The Herd with Colin Cowherd - 3 & Out - Jake Rosenberg: Salary Cap Guru joins the show

Episode Date: August 2, 2024

John is joined by the Philadelphia Eagles former salary cap guru, Jake Rosenberg. John talks with Jake about his role being a salary cap expert, working with Howie Roseman (22:01), and the importance and strategy that goes into every contract for every player (54:20). Later, the guys talk about the role that Jake is currently playing when it comes to NIL deals with the Oklahoma Sooners (57:43). Follow John on Twitter, Instagram and YouTube for the latest. Check out Gametime - the fastest growing ticketing app in the US, and the official ticketing app of 3 & Out and GoLow -  for tickets to all of your favorite NFL, NBA, NHL, NCAA teams. Concert and comedy show tickets, too. Go to Gametime now to create an account, download the app and use code JOHN for $20 off your first purchase. #Volume #HerdSee omnystudio.com/listener for privacy information.

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Yep, that's me, Clivert Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, The Clifers Show. This is a place for raw, unfilled conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to the Clifford show on the IHard Radio app, Apple Podcasts, or wherever you get your podcast.

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I'm John, this three and out podcast. You guys know the drill. Football was played Thursday night, but we're not going to talk any about that. Not that there's much to take away. But, and stuff is happening around the league. I saw Justin Herbert is going to be on the shelf for a little while with some foot issues. And that makes me reevaluate my charger bet,

which might shift to the bills. But today, we are going to be talking with, Jake Rosenberg. He was Howie's right-hand guy negotiating contract for a decade plus. Been with the Eagles since 2012 or 11. Me and him overlapped a little bit. And just left, starting a company to work with college programs. He's working with Oklahoma in the NIL.

And I just wanted to bring him on to talk contract for dummies, just some basic stuff. His story, his thoughts. a little on the NFL and just BS about money and football because, you know, understanding the way bonuses work, dead cap, not being able to sign guys because of it. I think he's got really interesting perspective because he's literally been a part of writing all these contracts, starting with Shady McCoy back in 12 to Carson Wentz through Fletcher Cox and Kelsey and obviously Jalen Hurd to take one Barclay this offseason. He just left, I think, a couple months ago.

So it's, yeah, it was cool. I'm glad me and him reconnected and asked him to come on the pod. And he said yes and fired up to have them on. We talked for, I think, about an hour. And that's going to be the podcast today. So no Fugazi Friday. We'll push that back until next week. And I'll probably do a big mailbag.

Not sure if I'm going on with Colin, we're going to do one on Sunday or not. But regardless, I'll have my own podcast. Might be a mailbag heavy because we've got a bunch of mailbag questions. We'll see. I mean, it's not like practices, stories are going to stop this weekend. So the next podcast will be Monday. And yeah, so obviously a lot of football content. Go low.

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Last minute tickets, lowest prices guaranteed. Okay, let's dive into Jake. Fired up, like I said, vice president of football administration for the Philadelphia Eagles. Before that, dude even slaying some commodities. There's a finance bro right here. He knows his numbers

and is now a partner in the athlete group helping programs like Oklahoma. I don't know if you ever heard of them, the Sooners. deal with NIL and the ever-expanding dollars that are growing in that world. So, yeah, Jake, fired up to have you. What's up, buddy? Awesome. Great to see you, too.

It's a reunion of sorts. How you doing? I'm great. Everything's good. You know, I'm not in training camp. I'm actually visiting my in-laws in Michigan in August. It's a strange new world I'm living in, but everything's great. just for everyone listening, you were, you leaving the Eagles was a pretty big story.

But I kind of want to rewind. Can you just give me a little background? I mean, I know it, but just for everyone listening, what you did out of college and then what led you, we overlapped a little bit in Philly and kind of what you've been doing for the last decade plus with the Eagles, Jeffrey and L. Yeah, yeah. I went to University of Pennsylvania, two years of management consultants, about 12 or 13 in commodities trading. I was on the floor at the Chicago Mercantile Exchange. I was off the floor trading bonds electronically with a group, built that up, did some stuff. Moved back east with my wife. My son had my daughter. But all the while I was sort of, I was looking for a way to pivot. I always wanted to work in sports.

I started a sports technology, a scouting app on a Palm Pilot in 2003. Failed Venture, but I got to know some people in the NFL, got a little bit of a taste of the whole thing. And then rolled out of trading, took an internship with the Eagles, had an opportunity. I commuted from North Jersey down to Philly for about 11 months. But really fortunate timing there. I stepped into an opportunity, primarily overseeing cap, contract stuff, negotiations. And then Howie and I worked really, really closely up until May 15th. And so I oversaw the financial side primarily.

But, you know, there's not a lot of people in an NFL front office. And having been there as long as I had and had Howie's trust in a relationship, I was involved in pretty much everything. You know, all the strategic decisions we made, a lot of the hiring and coaching searches and stuff like that. I got experience broadly, entire roster, staffing, etc. I want to speak really quick because I get asked a lot about younger people that have questions about their future or deciding whether to leave,

follow their passion and take a step back. Obviously there was a pivot point in your life. I would imagine you had done pretty well on, definitely on some given years with commodities. So to take an internship to fall of passion, how you were over 30 at the time. I'd imagine. 35. Yeah, it made a comedy about me starting an internship, kissing my wife and two children. Goodbye.

I mean, that was a pretty big financial. Do you remember what that internship paid? I honestly have no idea. But I. 50K? something? I mean, it couldn't have been. No, I don't even think I was making 50K as an intern, but it wasn't, it didn't last super long. And in full disclosure, typically when people are like crushing it in trading, they don't necessarily look for to, you know, to make career

pivots. My career in trading, unbelievable market timing when I first started trading, a lot of the electronic markets were just starting to come into their own. There was a lot of low-hanging fruit. It was, it was easy. I mean, for it wasn't, people didn't have these, these super advanced strategies weren't throwing a whole lot of technology at it. Um, so I did really well very quickly. Um, I had a lot of fun, enjoyed that life. Um, it was, it was very loose and lax and I was making money and it was great. But then as I got older, as the business got more competitive, a lot of capital thrown at it, a lot of technology. The Chicago trading scene was built on a lot of locals who had spent time in the pits where there's no technology.

You know, that's more just like playing a sport and reacting. And I don't know, a lot of us had a ton of friends that traded and a lot of people in the same situation where as business evolved, we were kind of stuck in what we were. stuck in what we knew and just sitting there playing a sport and people are like you know we're having we're fighting each other with like plastic forks and people are taking out machine guns it's you know so that all happened um in trading i loved the competitive side and how objective it was and there was no saying hey boss i did a great job i didn't have a boss but you couldn't weren't saying you did a great job. It's literally, I made money, I didn't make money.

How much money did I make? That's the scorecard and you really couldn't fight it, which is awesome. That's pure. That's very few businesses, I think, like that. And so that got harder and harder. I started picking up people and things in my life. And I never felt stressed trading knowing I never made a salary in the 13, not years I traded. It was all eat what you kill. And then it just got tougher over time.

And it was less like playing a sport and more like drudgery of, oh shit, I just put it in six months and I'm worse than where I started. But so that, it didn't make the decision for itself necessarily. But I was thinking at that point, like I need to figure out what's next. in sports has always, has always been my number one passion in life, without question. And so I was trading in New York, living in North Jersey. And there was a situation where the group I was trading with, our trading capital, was being held at a clearinghouse. That's supposed to be your money is just parked there.

It's not at risk necessarily. And there was some kind of issue where that all of a sudden, was held and we couldn't use it. And I'm just sitting there, not sure if we were going to get our trading capital back. And that was a breaking point. I was just like, you know what? I think this is a sign. There's just too much going on.

I need to figure out what to do with myself. And a few times I'd had conversations about whether I would be interested in doing some type of cap role or, you know, and taking this step. It wasn't something I could see doing when I was in Chicago. or when I was crushing it and I had tons of time, you know, an ability to kind of control my life. But then it was like, yeah, this makes sense. This is something that I really want to do. My wife was very consistent in saying this is a chance for you to do exactly what

you want to do. Don't sweat what's going to happen here because, as you know, this is a very difficult profession for wives and families. families in the sense that there's a lot of time. And my wife and I started dating and everything while I had a very easy schedule. We had a great life. We spent lots of time together. And then it pivoted to where I was at work a lot.

And for the beginning when I was commuting, leave an hour and a half each way. It was like 83 miles each way. So I'd be at my desk by 7 a.m. or so leave the house at 5.000. 30 and then get home, but left the office at 7.30 or on a week night. I'm not really seeing my kids during the week. So it wasn't awesome, but it was a means to an end. It was like something everyone else most people do in life. You got to do. Well, I wanted to do something with you called contract for dummies and, you know, millions of people watch the NFL and just no one comprehends these contracts. But you get out, you start working for.

for Howie and then within a couple of years Andy's gone, Chip comes in and within a couple years when Howie went on a sabbatical because you were working very quick, did that change your role? Did that all of a sudden become like what's going to happen here? Sabatical. I think that's what Howie calls it.

I think. I say we were in exile. It's fine. Did you get exiled as well? Oh yeah. I had a view of the dumpster over on Patterson. It was great. Yeah, I got exiled as well. I did a lot of the traveling around with Howie hitting up our networks and talking to teams and doing all kinds of stuff. And we were thinking, don't know if it's going to happen in Philly. But if it happens here or wherever it happens where we get a chance to come back and run a team,

let's make sure we're doing it in the smartest best way possible and not just the way it's always been done or the way we've seen here. So we talked to baseball teams, basketball teams, hockey teams, successful business people, and just got best practice on a million different things. So whenever we were taken out of the tower, out of exile, we were going to be ready to go. Who's your favorite conversation of that kind of little run? We had a lot of great conversations. I remember going down, we visited with the Braves. We talked to every, I mean.

Then you go San Antonio, R.C. Buford? How we became, how we, how we became close with R.C., yep, through that process. Bezos? No, we weren't in that type of spheres. No, sports-wise, I mean, at the time, we went to Chicago, met with the Blackhawks. the Braves. I mean, it was there was a lot of stuff.

We went to New York. We hit up, you know, some successful business people that we knew. Yeah, it was a really interesting process. And then I think actually,

it sort of still shapes the way I think. And a lot of the, a lot of what's gone on in Philly since how he came back. in 2016 is a direct result of that. You know, we talked to baseball teams and talked about player development and things that in the NFL are, you know, there's a thing where people sometimes will just throw their hands up.

They'll be like, ah, we can't do that because of like these five things, you know, and I'm actually seeing this in college right now, which I know we'll talk about later, but everything's just in total chaos. You know, this is a mess. we're screwed, you know, basically. Put your head between your knees, assume grass position. And player development in the NFL

because of the rules and because of how players' time is so carefully regulated how long they could be in the building for that period of time, eight or nine weeks in the off season, dead period between the end of the season and the start of your

off season, and then dead period from the day your offseason program ends until your report for training camp. people just think that you can't thoughtfully develop the back end of your roster. I think that's just a prevailing notion because you don't have enough time. It's a physical sport so you can't put extra physical demands on them. And then during the season, time is short, particularly on the coaching side. So it's rare.

You're not really going to ask your coaches to spend extra time to help develop players because they're heavily engaged in game planning and getting starters and key players ready. So I think that's the norm. And then when Howie came back after a lot of the things that we had seen, we'd seen baseball teams who were signing kids at like 16 years old who didn't even speak English. And they had seven years or six years to get them to the big leagues and function in American, you know, in American city they were going to live in. that's incredible amount of development, right?

You're teaching the language and customs and also trying to make them freaking good players. So that wasn't going to be what we did. But full-time development people, a legitimate formal program, you know, this is something as I ran like the undrafted free agent signing period for us for a long time. And when you're trying to get kids who are dejected that they weren't drafted, right and you don't have a lot of money to spend these are the things that you're trying to sell them on like look

we don't just sit here during the season and have our practice squad read cards and you know draw a big line in a sand like we'll see you next july we'll try to develop you then they have extra periods and there's all kinds of things where we're still trying to improve you and the coaches are are on it it's everyone is pulling that direction and i think those are those are legitimate takeaways from having a process like that you know, before we dive into contracts, you went on record to all the Philly people because that thing is covered like an S football team or something, the Eagles,

that one of your reasons to leave, it's not like you got fired or anything. I mean, how he didn't want to lose you was that your aspirations, you want to be a general manager in the NFL, correct? Is that fair to say? I would say that that has been my aspiration for sure. To do this,

to do what I did for every year and learn the kinds of things that I did and get that level of experience. It's like Stout says. It's like bars of gold every day. You know, you learn all this stuff. And so, yeah, I had ideas. I worked within a very specific system in terms of working for Howie and how all that went. But I felt like I acquired the breadth of knowledge and skills and I have the personal traits to lead an organization, I felt like I got the most incredible education in running a team. Even if you don't, you know, Howie makes all the decisions, there's no question about that. But I see people get hired in the NFL who have neither made decisions, nor have they actually seen it executed in terms of team building, organization building,

everything that goes into it. It's not just about picking players. You know what I mean? There's so much that goes into having a continually successful organization. There aren't coincidences. There might be a one year like lightning in a bottle type of thing, but you don't have the consistent success that the Eagles have had by coincidence. So I've seen how all these parks contribute to the whole.

and I've seen the way you can find edges in every single department in football, right? This isn't just about scouting better and coaching harder. Like that's, I think some people think that. And sometimes the people who think that the most tend to be the decision makers, it seems, that are making these hires. But yeah, I felt like I could run an organization. I would run it differently than Howie. My skill sets different.

Everyone's is. I would run it differently than most of the scouts who get hired. I would need to hire someone to oversee personnel. That wasn't necessarily going to be me. I wasn't going to be the head evaluator. But I didn't really see that as a challenge. I mean, you look at Fortune 500 companies, you know, they're pulling CEOs who are, who have strategic vision and can execute on that and build an organization.

It's not about one like tactical skill. And for me, I feel like that skill in the NFL is overvalued. See, I don't even think you need to go to the business world. Look at baseball and basketball. Correct. You were in your position with the success you had. You would 100% be a GM in basketball or baseball. Or at least have had, you know, maybe screwed up the interviews or whatever.

But you'd be interviewing. We're in football. I mean, you're closer to it than me, given that you've just been inside for the last 12 years. Is it safe to say that there's still stigma with someone like you? to be hired to run the personnel spot? I think it's not talked about as much. It's not talked about as much. I think, you know, even in Philly, you know,

Howie, like, was given a very hard time for a very long time for a lot of reasons that were, you know, beyond, you know, there was a background. By the time I got there, he was the boss and it was less, I think, than probably years previously. Yeah, you know, he wasn't going to roll with Andy. Right. And I think like the, his track record at this point is irrefutable. So he has risen above, you can't really say a lot of those things.

But the football guy, non-football guy, or what it's supposed to look like or what someone's background is supposed to be to run a football team still feels like that hasn't changed as much in the NFL as it has in other sports. I think that I have thought that there are owners or different profile of owners who have come into the league where, they would transcend, like break out of this trend. And I think there are advantages to be gained by doing things a little differently. Like we see that all the time. But it really hasn't happened in the league. So I had no intention of coming out publicly in the way that it did that I was leaving. You know, there was a, I had started telling some agents and people in the league that I was leaving May 15th.

One of our beat writers had heard it. And I wasn't telling people, hey, you know, don't say anything. And so he grabbed Howie and said, hey, I know Jake's leaving and I'm going to write an article about it. And then it was, well, you know, I'll talk to him because I want to make sure to frame the right way. This isn't a negative situation. No one's telling me to leave. I'm one of the few people who I, you know, I just basically stood up and walked myself out of the office. I left in great terms.

I talk to people, you know, in there every single day. I hope, I think players, staff, coaches will be my lifelong friends. I just stayed in my family and I stayed with a coach for two days at the shore a couple weeks ago. But, yeah, I aspire to be a general manager. Do I think that that's going to happen? No, I don't think that that's going to happen. My intent in that article was to try to balance the, this is the general manager. framing of what's going on.

I didn't want to close any doors. I didn't want to say I am leaving at this place, F the NFL. I never felt that way. And you never know what's around the corner, so I don't want to close the door, but I can't say my phone's been ringing off the hook at all,

which is interesting to me. But it means, honestly, it means that I read everything correctly. Which is crazy because you guys, you know, I'm a West Coast guy, Niners get crushed. for doing these contracts late and you guys get all the credit for doing them early. So it's like you guys had a point of difference that it get so much credit for with the financial ability to construct your team.

Obviously, you're Howie's right hand guy for the, where you did no one even call and be like, hey, we want you to run our cap? None after you were leaving? None. Even consult or like a Mike Brayble situation? I got one. I have one. One. Were you a little surprised by that?

Had you interviewed before for a jam job? No. Had you ever done a formal interview? No, I interviewed for a job in Washington. The day before my contract ended in Philly, that came up very suddenly, didn't know Adam, had no expectations of that happening.

I went and I did interview because I felt like for me, it wasn't that I was leaving in a, like I said, like not screw this place I'm over, I just felt like I had done this job for a long time. And I knew what the landscape was internally, you know. And so I wasn't necessarily moving up internally. I'd hired Bryce Johnston, 2016. He was doing a great job, and he loves doing a lot of the stuff that I don't love doing by any means.

And he's great at it. Like a fucking mad scientist, you know, contract guy. So that for the good of the team, I mean, you're giving stuff like that up. You're helping develop people, but I knew I wasn't going to pick up and learn different areas necessarily in Philly. And for better or worse, I was never, yeah, in the NFL, there's a balance between putting yourself out there and like, you know, versus being the guy who is a self-promoter or always kind of looking for the next. next job before he's even settled into his current job. I think that that's a balance. The stability in terms of being in one place from a whole career was awesome. My kids have been in the same schools, you know, their entire public school life or their entire, you know,

grade school life. Yeah, yeah. But is there at some point, I think, having to work so closely together, we did so much of this together, agents. I think with most people just to, assumed I would either never leave or want to leave. And so I just was a little bit of the part of the furniture. And when I did tell people I was leaving, I still don't think a lot of people thought I was really going to do it. Like I was some type of like bluffing or negotiation strategy. But no, I did it.

Praise. I've known Adam even before I got Philly. He's a good example of a guy that, you know, in a league full of stuff. promoters, it's not really his style. It's not really his. It's not really his. And it's hard, right? Because it's such a public job and the money is so much greater with every step you take, whether it be an assistant coach who coordinate the head coach or be the third in command

to assistant GM. It's tricky. And now the game's never been more popular. Like you said, the moment when gets out that Jake Rosenberg's leaving, you got a beat writer and other people get win. But I think more and more NFL teams are being. you know, being covered like that. And it's only going to grow, at least for the foreseeable.

Yeah, I think that my story, or at least this was probably covered a little bit more than normal is because it's odd. Yeah, that's fair. It's odd. I was like Jerry McGuire, you know, grabbing goldfish and running out of the office with Dorothy Boyd. But, yeah, I didn't really feel that way. But I think that was a little bit of like, wait, there's got to be an angle here. There really was no angle. And especially because the team, right, obviously it didn't finish.

It's great, but there should be pretty good this year. And you've had a good little run. No, it's been a great run. I know. It's been great. There's never a good time. And I kept telling myself, when I leave, just like the day after the season ends, when you feel the absolute worst, you know, you feel like you got punched in the nuts.

That's best time. Just leave. That's your last day. Cool. I'm out. Once you stay, once I stayed through free agency in the draft and all that stuff, then it tugs at your heart. You feel like this is my team now.

And I'm rooting for them. I hope this is a great season, but I'm not, I'm, if this gets to where I hope it does, well, I feel a little bit of like, man, I could have stayed through a Super Bowl season or something, sure. But you got to just pick a

point and make it happen. Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced games. Some call it grotesque. others say it's unleashing human potential. Either way, the podcast's Superhuman documented it all, embedded in the games and with the athletes for a full year.

Within probably 10 days, I'd put on 10 pounds. I was having trouble stopping the muscle growth. Listen to Superhuman on the I-Hard Radio app, Apple Podcasts, or wherever you get your podcasts. A win is a win. A win is a win. Yep, that's me, Clipper Taylor the 4th. You might have seen the skisks.

hits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment, and the next we'll talk about life, mental health, purpose, and even music. The Clifford Show isn't just a podcast. It's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger.

So, if you've ever supported me or you're just chasing down a dream, this is right where you need to be. Listen to The Clifford show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. Do you remember when Diana Ross double-tap Little Kim's boobs at the VMAs? Or when Kanye said that George Bush didn't like black people. I know what you're thinking. What the hell does George Bush got to do with a little Kim? Well, you can find out on the Look Back at it podcast.

I'm Sam J. And I'm Alex English. Each episode, we pick it here, unpack what went down, and try to make sense of how we survived it. Including a recent episode with Mark Lamont Hill, waxing all about crack in the 80s. To be clear, 84 was big to me, not just because of crack. I'm down to talk about crack on day, but just so you're just so you're

y'all know. I mean, at this point, this is the second episode where we've discussed crack. So I'm starting to see that there's a through line. We also have AIDS on the table right now. Thank you for finishing that sentence. Yes. I don't think there's a more important year for black people. Really? Yeah. For me, it's one of the most important years for black people in American history. Listen to look back at it on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Okay, contracts for dummies. Yeah, here we go. When you're dealing with bigger star players,

AJ, Jalen, whoever, what is the first thing on the team side? Where do you start? Well, I do think that that changes. That's a little different by team. Different teams prioritize different things. I think for us, we prioritize cash flow. in terms of fewest dollars out the door fastest. In the NFL, there's a theme here in my mind in terms of managing cap or doing contracts.

That's consistent with everyday life or being in the market, you know, wealth advisor, etc. is you need to be responsive to what the current market situation, what your outlook is, right? Like, you shouldn't necessarily have the same stock bond allocation that you did 10 years ago. Now, if the interest rates have changed and if all these other things have changed. I'm just using an example, right? You always should look around and say, is this still the best way to do it? So I think the way that the league has gone, having more options in terms of players get traded more readily, but things are a little bit more contentious maybe.

Player empowerment is higher now. So I think the idea that... I think you're seeing it all around the league during training camp with these holdings, the guys pissed off. I mean, you can name 10 off top of your head. Yeah, I think it's been increasing every year for a while. I think NBA set the trend to some extent in terms of players who become the foundational piece. The entire thing is built around them.

And then they decide one day, like, get me out of here. And that to me is like, oh, my God, it's maddening. The league players have certainly gotten a bigger voice and have been able to sort of force their way a little bit more. So I think it's even more important to maintain, you know, optionality. It's like, you know, the example would be, you know, Jordan Love, if you, if a lot of cash leaves the door in year one, and this isn't going to happen on a deal like that.

But, you know, if it's a, we'll pick an example, if it's a $50 million average to use a rough number, right? And you pay $80 million in the first year. And then there's only $20 million coming to them in the second year. players don't necessarily have the perspective to be fair about looking backwards, they look forwards. And so all of a sudden, it's like, I know or you know that there's an average to this deal, right? And there may be big cash flow in the beginning, but then it's got to come back to the average over time. Player just looks forward and he's like, man, all these guys are making $50 million a year and I only have $20 million coming to me.

And then you're like, yeah, that's because you got 80 last year. You're like, no, I only have $20 million coming to me. That's crazy. I'm not playing for that. And so I think that's one part of it. And then secondarily, trading players has become a much bigger part of it too. And if the money is still in your pocket, meaning it's going to be paid in a salary or a roster bonus or some other way, you could trade it until it's earned or paid.

and so there is an advantage to on a $50 million deal, I'm just saying, having 50, 50, 50, 50, rather than, you know, 90 and 10 or whatever. Normally it's normally it will take a little bit longer to come back to a baseline average. But you understand the point. I think cash flow is a big thing. And players want the cash in their hands faster for investment reasons. I think, yeah, Jordan loves a good example because I was looking before we hopped on. You got a $75 million signing bonus.

And typically I always thought when you get a signing bonus that comes within like a 10 to 14 day period. But you can write it out. Like his is 125 now, 25 in October, 25 in December. Is that one that people argue over a lot? Yeah, because it's become a thing where certain teams will defer it a year, two years. out. So signing bonus really means you've earned it when you sign, right? It doesn't mean it's paid out right when you sign. And how soon it's paid out is absolutely negotiated. Some teams, it's just organizational policy or they'll say this is their precedent and they will hold on to

it for a while. So, you know, to use the Bobby Bonilla type of thing or Shohei Otani or their deferrals. I mean, you are deferring it. So the longer a team could hold on to the money, it's worth less in present value, but that's not necessarily the intent of it. And but that is a point of negotiation. And with draft picks, particularly in the first round, that's turned into one of the items that is negotiated, how fast they get their signing bonus. What about the escrow thing? That's something you dealt with a lot? Oh, yeah. Funding. If I guarantee.

Yeah. So if I guarantee Jordan Love, let's just use that. There are other numbers, but that $75 million signing bonus. Do I have to have the $75 million signing bonus on in reserves, even if my next two payments, one's in October and one September? How does that? So typically they don't necessarily go all the way to the next funding deadline. But it really is about fully guaranteed payments in subsequent years.

I really am afraid we're going to lose people here. You're going to see people like going samurai style. There you go samurai style like airplane. So January 31st is the funding like threshold. So anything that's fully guaranteed as of January 31st, what hasn't been paid out yet is subject to funding. And then by April 1st, with some other little permutations, the team basically needs to move however much money

there was as of January 31st that qualified into this escrow account. Now, anything that becomes fully guaranteed after January 31st is not subject to that April 1st. So that's why you see a lot of guarantees that are intended or the spirit of it is to be fully guaranteed, but not vest to fully guaranteed until after January 31st. January 31st is before the Super Bowl. So it's a prior season. The first day of the waiver period is really the earliest. You'll see someone have a vesting date, like the Monday after the Super Bowl as a 4 o'clock.

Most teams don't want to do that. That happens very infrequently because it puts them in a very difficult situation. You really can't do anything with a point. player there. You have no optionality to keep using that. So very typically, first day league year, third day league year, fifth day league year, you'll see an injury only guarantee turn into a skill injury and cap guarantee because if it's for the following year, it would have to be funded following April 1st. If that makes sense. Let's pick the number 50 for guarantee.

guarantees and then or true guarantees and then we'll go to a hundred for the injury guarantee. Am I doing that backwards? No, that's right. The full guarantee, it'll be less. Explain to me, can you explain to people what the differences of the guaranteed and the injury guarantee? Yeah. Injury guarantee is a guarantee that, so there's three buckets you could cut a player under a skill. which means the player from a skill perspective is not worthy of being on my team. Injury means the player has not kept himself physically in condition to be on my team and cap,

which is a little bit tougher to explain, but basically I could find the same kind of player at a lesser price. That's more or less it. So the most valuable guarantee is skill injury and cap. that's synonymous with full guarantee. And that means that outside of a few conditions, more or less an injury that's not sustained murder would be one. An injury, you know, not on a football field somewhere or in a football building.

It's very difficult to cut that player, right? you effectively that's full. An injury just means if the player is healthy and you don't think he's good enough or you think his number's too high, you can cut the player. You just can't cut him if he's hurt. And typically those injury guarantees will convert at some point to a full guarantee. So yeah, and so that winds up being, that comes to the forefront in the forefront in the sense that typically that conversion date is, like I said,

it's either in the waiver period or within the first few days of the league year. If a player is injured from prior season and by that vesting date is not healthy, you would not be able to cut him and that guarantee will vest to full. And so the behavior that that winds up triggering is when you have a player that you're almost certain that you are not. going to want for the following season who has a guarantee that converts it's dicey putting that guy on the on the field in the prior season because a major injury he sustains will basically mean his salary for the following years guaranteed or some part of it depending on i think the best

example because russell was a different example because he had so much contract left it remember two years ago derrick car with the raiders yeah the last three games i think the number would have been like $25 million or $30 million. That happens. And so they got bench. The Russell thing is a good example of when you have these huge guarantees. I think one people struggle with the dead money. Because when I do a signing bonus and the guaranteed, if I push that back on my cap,

so my cap that's smaller, early, bigger later, if I cut that player, I, you're Russell Wilson. That accelerates forward. Is that correct? You're using all the right words. I like it. I would say, you know just enough to be dangerous, is what they say. The dead money is money that has been, so you have the ability to pro-rate bonuses in the NFL, right?

Any money, like paid an assigning bonus, for instance, you could pro-rate up to five years. So you divide the amount of the bonus, divide it evenly amongst the first five years of the contract, and it keeps the cap number lower than what the actual cash at a price. pocket, right? Player gets it all. Pro ration has nothing to do with player payment. And then if at some point, that contract gets terminated, any of these pro-rated amounts that are out into the future will come back onto your cap, depending on whether they're before June 1st or after, whether it's this season or the following season, that's where you get acceleration. I think that the term dead money.

is bandied about thrown around in press conferences you know there's like fear factor about dead money there are a lot of people

talk about well our cap wouldn't let us do this and you know we're in cap hell we're doing all these things to me those are those are not well thought out strategies and you should never not

if you're not able to do what you wants where your owner is willing to commit X amount of cash in a current season, regardless of how miserable certain things look about your football team as far as the contracts and the structure, you should be able to figure out how to spend the cash. To me, it's a huge fail. And fans just take that. They're just like, oh, okay, cool. We're in cap hell.

We'll see you in three years. Maybe we'll be competitive then. Like, I think that's crazy. but there are some instances when you say like let's use Russ Wilson as an example because he had so much contract

but those numbers are pretty prohibited and just pretty massive I mean I think aren't they historic they're massive like yeah I mean it doesn't mean you can't do stuff it's just too right

it doesn't mean you can't they technically could they technically have eaten a whole thing this year like eight five millions that split it out I think that correct depending on when they did it and how it worked

but the issue that I think is you always have players who have salaries that are larger than minimum that you can restructure to pro-rate amounts. So you have a lot that you can do. It just comes back to what is your philosophy on managing cap. And I think a lot of teams will tell you, or they don't need to tell you, you just look at their contracts and look at what they do. And you will see that most of what they do is the exact same structure. that they used, pick a point, five years ago or 10 years ago, which is what I just sometimes my eyes glaze over about because part of this, there's an art to this.

You have to anticipate where the cap is going to go in what the current economics are. If you're doing something the exact same way you did under completely different circumstances, says, I just think you're not doing a great job. I'll just say that. I think this offseason, you guys took advantage of something that once, what, three, four years ago was looked at crazy. Then these running backs became a major discount. I mean, it'd be like a million dollar home five years ago. Well, it's now worth $650,000.

And Sequehuan Barclay, you guys sign them. He gets less than 30 guaranteed. but I look, his cap hit this year is, I think, less than $4 million. So when you do something like that, there has to come a time where some of that money gets allocated on and give you're bigger. But this year, you could, like Jaylen last year, wasn't his cap hit really, really small? Yeah, I think that this is right. These are all parts of larger strategies, I would say, in terms of just maximizing how much cash you could spend. If your ownership wants to spend in excess of what the salary cap is in a given year,

if you use proration well, you should be able to do it regardless of these other albatross sort of dead money things that you have. I mean, this is a feature, not a bug of the way that better teams manage cap in terms of if you are planning and doing scenarios, you shouldn't have to cut players because of a cap situation. You shouldn't be hamstrung from adding players because of a cap situation. You just don't want to. That's the reality of it. Or you're not creative. Some owners have more cash than other.

Right. But my point would be even if you have someone who's got $50 million of dead money on your cap, so you have this $50 million hole, if you will, that you can't spend on players, just utilizing proration really well, you should still be able to spend $200 million of cash. Yeah. So it's just how you want to present it. It's not that you can't. It's just you don't want to.

It's an excuse. It's not. What about the mechanisms when it comes to the salary gap on trading guys? You were part of when Carson was traded and a couple years ago when Matt Ryan was trade and they had big, a lot of money and cash paid. Is that more complicated than just all out cutting a player than Russell? No, not complicated. The benefit of trading is they take these cash flows or they take, if there's guaranteed

money, they're just taking that dollar for dollar right off of your books. The acceleration part of it is the same as if you would cut that player at that particular moment. So if it's before June 1st, any acceleration, any of the proration that you had on there comes back into that year. But the advantage to trading over cutting is that guaranteed monies leave, right? Or no longer your responsibility. If you were to cut a player who has a full guarantee, you're on the hook for paying that full guarantee. If you were to cut them. That makes sense.

Yeah, it does. What's your favorite contract you ever worked on? my favorite contract I ever worked on, man. I don't know. I'd say like 2012, LaShawn McCoy, maybe. I don't know. Certain reasons I can't say,

but I mean, I love LaShawn McCoy. I've seen him in a long time. But I love that. I also would say Jailen's too, because I love Jalen. I have a great, great personal relationship with Jalen. I think the world of him is a person. Tons of respect for him.

And I really like Nicole, too. Nicole and I worked awesome together. I appreciate what she's done. It's been a meteoric rise. I don't know of any agent whose first real deal was a franchise quarterback type deal. So that's incredible. And that's, yeah, I mean, ultimately, whether or how, he was having the day-to-day conversations on a particular deal, whether I was more involved,

how it worked. It really is a very incredible thing to see in your very eyes. I sat with every single player who signed a contract while they were signing, and you're just part indirectly. I mean, you're watching someone's life change instantaneously, everything they've worked in, you know, I've worked for and put in. That is an incredible, incredibly powerful and awesome, awesome thing. I mean, I've seen it with so many players I love, and I've seen how they change, too, like for the better over time and grow. It's incredible.

Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced games. Some call it grotesque. Others say it's unleashing human potential. Either way, the podcast's Superhuman documented it all, embedded in the games and with the athletes for a full year. Within probably 10 days, I'd put on 10 pounds. I was having trouble stopping the muscle growth.

Listen to Superhuman on the IHard Radio app, Apple Podcasts, or wherever you get your podcasts. A win is a win. A win is a win. I don't care what I'm saying. Yep, that's me, Cliver Taylor the 4th. You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement

to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment. And the next, we'll talk about life,

mental health, purpose, and even music. The Clifford Show isn't just a podcast. It's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger. So if you've ever supported me or you're just chasing down a dream, this is right where you need to be.

Listen to the Clifford show on the IHeart radio app, Apple Podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. Do you remember when Diana Ross double-tap Little Kim's boobs at the VMAs? Or when Kanye said that George Bush didn't like black people. I know what you're thinking.

What the hell does George Bush got to do with Little Kim? Well, you can find out on the Look Back at it podcast. I'm Sam J. And I'm Alex English. Each episode, we pick it here, unpack what went down, and try to make sense of how we survived it. Including a recent episode with Mark Lamont Hill waxing all about crack in the 80s. To be clear, 84 is big to me, not just because of crack. I'm down to talk about crack on day, but just so y'all know.

I mean, at this point, Mark, this is the second episode where we've discussed crack. So I'm starting to see that there's a through line. We also have AIDS on the table right now. So, I'm finishing that sentence. Yes. I don't think there's a more important year for black people. Really?

Yeah. For me, it's one of the most important years for black people in American history. Listen to look back at it on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. When you see these situations, I mean, you know, former Eagle, Hassan Reddick, this Matt Judon, when you're having these conversations and a guy wants more money, Sometimes it's like, well, we don't have the capability. Like, this is not something we're that interested in, and we really don't have the room to do what these guys want.

Like, you just have to draw a line in the sand. Like, do you always know there's like a line or it's, I mean, I know Howie and you guys, feels like that can move. Like, well, we can make this work if we really want to work. Like, you've been kind of alluding to this whole time. Well, yeah, I mean, but you have a roster of 53 players. You know, if you only had a couple of players and you make an exception for one, that's fine, but you know that then you're going to have 10 more players at your door.

It's no different than if you have kids and you treat one different than the other. So I think that it's that you can do it, but the complication of all these moving parts and when things have some level of equilibrium and you feel like people are relatively happy, your team is stable, when you have to put yourself in a very difficult situation. I mean, the nature of the job is how he has. a ton of decisions every single data make. Some of them are relatively minor.

Some of them are significant, people never even know about. But when a player is asking for more money and you're making an additional commitment going forward, you're looking at your entire team, the whole balance. You're looking at where you are next year, how old the player is going to be. Then you're looking at analytics

and where do players fall off because no player maintains their performance forever. So you're always afraid of being one year or two, late rather than one year too early. It is, yeah, it's complicated. There's a lot there. It's easy to second guess if it doesn't go well. But it's not easy.

No. I know I've kept you a long time, so I want to hit on the athlete group, and I know you parted with Oklahoma. I was talking to a buddy of mine that runs a major Power 5 team, and he was telling me about this guy, they gave $800,000 high school recruit. And I was, I knew you were coming on. I was thinking, what is the, what's the draft slot? where it's $800,000 cut off.

Like, I mean, we talk about, is that mid-second round? I mean, that's pretty high. Yeah, no, it's a lot of money. It is a lot of money. I would say that I've heard far larger numbers. But I also would stress. This was a lineman, not a quarterback.

Yeah, yeah, alignment. This is just an 18-year-old lineman. Yeah. No, I have heard a lot of those things. Well, I'd say, like, my role, though, I am not. negotiating on behalf of a team. They're not outsourcing team building to me by any means. My main function here in college sports right now, the way I see it,

is these programs as a whole. It may be an athletic director that wants to assess where they are now versus where they need to get to, or it's been lately a lot of football offices themselves who realize that they need to help, that they're just not structured in the right way. You're not equipped to evaluate this many players, to understand how to live in an environment where building your team is based on allocating assets

and spending money, not about just recruiting the crap out of players. Like it's a completely different mindset. It's a completely different process. If you're going to evaluate, I don't know exactly what the number is, but with the portal, if it's twice or three times the number of players that you have in the past, how do you adapt to meet that need?

You know, evaluating players is far more important than it was in the sense that you have that many more. And you got to compare, you know, is it a one-year portal fill in? Is it building through high school, which roughly equates to an NFL draft versus NFL free agency being the portal? How do those prices compare in terms of what you're going to have to give a kid out? of high school or maybe it's two players out of high school equal one portal guy. And is that better for the culture? There are just so many different changes in mentality that need to go on to build a team in this way.

You know, the first instinct, everyone always thinks about it is like, oh, well, I could help them me personally with my background. I could help them figure out how to pay better, like what the comps are, how to effectively match a player's salary with the quality of play. And I believe I could help. There are certain techniques or things we could do. But the real issues at heart here are that the way college football, I'm saying college football,

because it's the easiest thing to talk about the moment. But college sports as a whole, the way they've operated going way back, it no longer is effective anymore. There's just so many new dynamics. And if you are scouting, recruiting, everything, the way that you have done in the past, this has actually been a theme for however long we've been talking, but that you have to adapt.

You have to look at what is the situation right now? And are we best set up? Are people doing what they're best at? Do we need to specialize? Like, how do these things change? You know, coaches do what in college football? Coaches coach? They recruit and they scout.

Coaches in the NFL do a little scouting. They don't do much, you know, a little recruiting, sort of. The coach. And what do scouts do? They scout. And if you watch a player, if you watch players all day, every day,

that's what you do. You're going to get better at it. If you are splitting your time between three different things and you're watching players and, like, it's just normal efficiency and whatever you, save in terms of efficiencies,

resources, flow to the players. So everyone in that office now, they're used to having analysts, you know, up the ass. Save an analyst, they had a player, maybe. If you find improvements elsewhere, that's the reality of it, you know,

efficient. So you partner with Oklahoma who's going into the SEC and obviously a lot of pressure with the money that's going to be involved there. you immediately, I saw you were down there within the last couple of weeks, right? You go meet with Venables, the athletic director.

How do you even get like your hands around this? Because in the NFL, there are rules. Yeah, right? I mean, you get a punch a little bit. There's no rules. It's a lot. It's a lot more relaxed. Yeah, I mean, in terms of, you know,

I've never done this before. Oh, I did. I imagine we consulted, like when I first got college, but I knew what my background was, what my experience was, and how I thought I could help. I know I can help now after having conversations with, you know, AD, head coach, GM. Like, I know I have a lot I can help them with. And not just me, this whole thing, you know, my idea here with athlete group in this business is that my network is probably the best thing that I have going for me. like I know a lot of people.

I've built a lot of great relationships. There are a lot of people who are looking for ways to help who are in the NFL, you know, in the NFL one year, then they're out of the NFL. And they're looking to consult. They're looking to help evaluate. And I figured to myself this problem in college football, there's going to be things that I'll encounter in one of these engagements where a scout needs to help them. A scout needs to work through a better grading scale or a better way to evaluate. wait, I know those people. I'll bring in great scouts to work with them.

I'll bring in great coaches who can sit there and talk to the coaches and explain why they might be better off if they're not primary evaluators. And I thought it was a great way to use my experience and what I've seen. Help them, help make a difference now because this is, this thing is coming. You know, and everybody needs to help. It's here. Oh, it's here. But in terms of like this hard cap and it's not just like asked for more money to the collective, it's, no, there ain't no more money. there ain't no more money, dude. You got to figure it out. And so I thought I could

legitimately make a difference. I could explain this is every day. This is a different way of thinking than what they have thought in the past. And so I'm going to see how I can help. And I'm going to see every school will have a little bit different plan or what they need. I think I'll help some schools hire. I think I'll help some A.Ds just get the lay of the land and because 80s are a little panic too. They don't know what's going on either. This is their money that's going to be spent. So that's what I'm helping with.

If you had to, I know you've just kind of dip in this last couple months, but I've got the lay in the land. Do you think a potential NIL cap is on the horizon as college football kind of figures everything out? I mean, it's going to be too hard to happen. I'm not involved in any of these, you know, conversations at a high level, but whatever,

what, whether this. Would you recommend that? Would you recommend that? Executed. An NIL cap, no, because I think players are worth, players are worth. And no one is really going to be capping that in the sense that if a player has a huge social media following, plays a premier position, is in a premier college,

and has the opportunity to move the needle and sign, I don't know, pick a sponsor or whatever. You know, whoever, a Bose deal. $5 million. That's legit. And they should be allowed to do that. It's just a question of the pay for play type of stuff that has been disguised as NIL. And if there is a good way to take that out, and then you have a legitimate cap, you will have players who still can monetize if they're able to move the needle and do stuff like that. And that seems like a much better system.

But there's a lot of you need to keep on order there. That's always the issue. I guess I separated the two. I looked at pay for play, which is technically illegal, but it's obviously happening everywhere. There's the guys getting the commercial stuff, which I guess I didn't factor. Obviously, that is an I L.

Yeah. I almost think it's different because pay for play is pretty out of control right now. Yeah, the paper plays are going to come in-house, though. I think that the revenue share and the settlement schools will opt in, they will get rev share, and they will know each football program, for instance, will know what they have to spend. on players. The question is above that from an NIL perspective, how that functions and whether the cap becomes the floor. What was it, Jordan said? The roof is the ceiling.

Yeah, the ceiling's the roof. Yeah, sorry. Or whether the cap is the floor and these schools that have these huge collectives can still pile money on through other means. That would be, that would be a little sad to me. I like caps. Caps are fun. They make you, really be strategic and solve problems and try to build a better mouse trap and not just it's not just a crazy arms race yeah I know you got to go but eagles 49ers part uh part two uh nFC championship game this year I'm here for it I would love it I'll be there because that yeah I'll be there that I don't want to get into it but the amount of the amount of whining and crying and like was so unbecoming.

Unbecoming. Take it. Just take it. Just take it. That's it. A year later, we saw the No, if this didn't happen. Yeah, but there was no crying. There was no crying. Look at the Super. And it did. I'll just say this. I'm proud of this. It didn't. Look at this. We lost the Super Bowl. Very, very,

like. See, now you're crying. No, I'm not. I'm saying we all know that to have happened. There was not a single trace of that from a single person within the Philadelphia Eagles. And I like that approach. Different approaches, different people.

I'd say Bradbury's a little quieter. Not just him, though. Everyone had an opportunity. I mean, come on. Anyway, you guys said it. I mean, you guys just got a blessed. All right. Yeah.

But I hear, I think the Eagles are going to be good. I've been on a regular. Oh, so. Yeah. So I'll be proud. I'll be happy for everybody. The line's going to be good. Packers going to be it.

The NFC is going to be really good this thing. That's what we think. We'll say what happens. That's why we all watch. You never know. Okay, Jake. Good luck. Keep rocking and rolling.

And don't forget about us in two years when you're in NFL team. Run the show. I wouldn't hold your breath, but cool. The volume. Another podcast from some SNL late night comedy guy, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Bob Odenkirk to David Letterman, help make you funnier.

This week, my guest, SNL's Mikey Day and head writer, Streeter Seidel, help an a cappella band with their between songs banter. Where does your group perform? We do some retirement homes. Those people are starving for banter. Listen to humor me with Robert Smigel and friends

on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts. A win is a win. A win is a win. I don't care which I'm saying. Yep, that's me. Clifford Taylor the 4th. You might have seen the skits,

my basketball and college football journey or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, The Clifford Show. This is a place for raw, unfilled conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated.

So let's get to it. Listen to The Clifford show on the Iheart radio app, Apple Podcast, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok podcast network on TikTok. Imagine an Olympics where doping is not only legal but encouraged. It's the enhanced games. Some call it grotesque. Others say it's unleashing human potential. Either way, the podcast's Superhuman documented it all, embedded in the games and with the

athletes for a full year. Within probably 10 days, I'd put on 10 pounds. I was having trouble stopping the muscle growth. Listen to Superhuman on the IHart Radio app, Apple Podcasts, or wherever you get your podcasts. This is an IHart podcast. human.