Toronto Mike'd: The Official Toronto Mike Podcast - Leigh Steinberg on The Kawhi Leonard Saga: Toronto Mike'd Podcast Episode 1969

Episode Date: September 10, 2026

In this 1969th episode of Toronto Mike'd, Mike chats with legendary sports agent Leigh Steinberg about the ongoing Kawhi Leonard saga.A version of this podcast without programmatic ads is available to all Toronto Mike'd Patrons at patreon.com/torontomike.Toronto Mike'd, an award-winning podcast, is proudly brought to you by Great Lakes Brewery, Palma Pasta, Ridley Funeral Home, Nick Ainis, and RecycleMyElectronics.ca.If you would like to support the show, we do have partner opportunities available. Please email Toronto Mike at [e-mail]. Hosted on Acast. See acast.com/privacy for more information.

You've got to be aware of the inbounder here if you're filling. It's off the Leonard, defended by Simmons. Is this the tagger? Episode 1,969 of Toronto-Miked. An award-winning podcast, proudly brought to you by Great Lakes Brewery. Order online at Great LakesBeer.com for free local home delivery. in the GTA. Palma Pasta.

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And Ridley Funeral Home, pillars of the community since 1921. Today, returning to Toronto Mike to discuss the Kauai Leonard saga. It's Lee Steinberg. Hi there. Lee, how you doing? I'm good. Good to see you again. Nice to see you.

How are you doing these days? How are you holding up? I'm doing great. I've been on book tour with my new book, The Come Back, and I'm working on a concussion foundation that we established to deal with collision sports injuries. And the season's back, football. Right.

Oh, that's always a big thing. Busy times for you. Yes. For the listenership, just before we get into it, I know we only have limited time, but for the listenership, I want to let them know. Lee Steinberg made his Toronto Mike debut in September 2024. And Lee, I'm just going to read the description I wrote at the time. In this 1,549th episode of Toronto Mikeed,

Mike chats with sports agent, Lee Steinberg, about his 50-year career, negotiating over $3 billion in contracts for players, including Troy Aikman, Steve Young, and Patrick Mahomes, his fall from grace, his redemption, that would be your comeback, and whether he's the inspiration for Jerry Maguire. So we had a good chat there in September 2024.

But today, if it's okay with you, I'd like to dive into this Kauai Leonard saga. How does that sound? Sure. So I'll set the table by just like dropping three dates and what happened on these dates. And then I'm going to just be quiet and listen to you. You're the greatest sports,

one of the greatest sports agents in history. So I'll just be quiet and listen to you. But these are the three dates just to set us up here. June 30th, 2026. This was the day, that the Toronto Raptors, my Toronto Raptors, and the LA Clippers agreed to this blockbuster trade. Kauai Leonard back to the Raptors for Brandon Ingram,

Grady Dick, a couple of first round picks, two second round picks, a 2027 first round pick swap. That was June 30th. We all kind of got excited over here. Then July 9th, the Raptors announced they were putting the deal on hold because the NBA was investigating whether the Clippers circumventing, Vented salary cap rules in connection with Kauai Leonard. So that was July 9.

September 2nd, just about a week ago, the NBA completed its investigation and hit the clippers with enormous penalties like $30 million fine, five forfeited first round picks. That's 2029 through 233, a one-year suspension for Steve Balmer, and they fined Kauai Leonard $700,000. Now, Lee, I'm tired of my own voice at this point, but I don't know if I'm coming or going. There's so much going on here. This deal is still not finalized. Please, talk to me from your perspective what you think of what went down, the punishment. I want to hear from you.

The NBA has a salary cap, and the goal is to create parity between teams. So all money that's paid by a franchise to a player needs. or every other benefit needs to be reduced to money, and then a formula is used with it. What is alleged to have happened here, and alleged from the NBA standpoint is no longer an allegation, but a finding, is that the Clippers found a way to add extra compensation

to the package they already agreed to him by arranging for outside commercial enterprises to compensate him for basically being quiet Lennard. The NBA decided that was just disguised compensation that they were pulling out of the salary cap to give them lower cap numbers, but it should have been properly reported. And because of that, they went ahead and gave a death penalty type penalty to Steve Balmer, kicking him out for a year where he can't be with the club Lawrence Frank, I believe for six months. There were five first round draft picks. So it's not only a punishment for today, it's a punishment that takes away the ability for the club to get much better. So it doesn't press it well for the future. Kauai Leonard got to find $700,000. But whatever the deal was, the union made in terms of signing on to this,

agreement, it did not involve suspension or time away from the sport. So the trade was put on hold, but I would expect that trade to go through. And Quy Leonard had his best year ever last year and is still at his age at the top of his game. So at the end of it, Toronto will be happy. And the poor clippers, you know, will be struggling to maintain relevancy. Were you surprised at how hard the NBA came down on the clippers? This is a very touchy issue. And it was also played out years ago in the NFL. Because in order to circumvent the salary cap and,

essentially put more good players under the same cap numbers. A club may be tempted to put together public relations deal, some side deal, money that's never reported, and the leagues are dead set on enforcing uniformity to the way that people report about their expenditures under the cap. So this was not messing around. It's sad for those of us in Southern California who have been Clipper fans because Steve Ballmer has been a great fan owner. And the team is in a brand new facility. So it's a chance for a resurgence. but these limitations make it very difficult to rebuild.

Without a doubt, now, in 2019, when Kauai played his one and only season thus far with the Raptors, he, of course, led us to NBA championship, or one and only, flags fly forever, Lee. So he had a lot of power coming off that season, and of course he chose to go home to L.A., but when you represent superstars, I named dropped a few off the top. Like, is it typical for a superstar player like Kauai Leonard to have this much leverage when he's a free agent? Yes. And the reality is that if he has contractual freedom at the point that he's hitting a peak in terms of performance, then he's a franchise. builder. He's

someone that by his presence alone changes the dynamics of a team. And he's that good. And he doesn't look to be slowed down any. So the

answer is yes, he had leverage. Now what you do with a free agent is sit him down and you say, look, let's make a list of priorities. How important is short-term economic gain? What about long-term economic security? What about family?

What about geographical location? What about being on a winning team? What about the quality of coaching? And you make a list of what the priorities are. So in that case, he valued going back to Los Angeles because he basically could have gotten better deals elsewhere and similar deals easily. So, but he made, made that choice.

And now the Clippers have sent him back to Toronto. And Toronto is a very desirable city. It's one of the five great cities in North America. And it's got multiple advantages. it's not like he was sent to exile in a small market. You know, he goes back to a place where he's a star with huge corporations and companies and sponsorship opportunities and a multi-ethnic population base, a place people want to live. Yeah, and we pay our players in American dollars.

So there's that too. But when I go back to 2019 for a moment here, I remember, you know, there was a lot of noise in Toronto about trying to get Kauai to re-sign, right? Like the whole city was trying to like recruit the man. Hey, sign here. We can win. You know, we can have a dynasty here. Stick around.

And then when he chose L.A., I recall, he had one stipulation that he wanted Paul George on the team. So I'm wondering, you talked about the leverage that superstars like Kauai Leonard have. But how commonplace is it for like a free agent to be like, get me this guy, this specific player, and they'll come? LeBron James did this multiple times. And he assembled in Miami and different, someone who is at that level. And LeBron James arguably for years,

the best player in the game, why Leonard not that far behind him. And so they do have the power. It just, it didn't work. Paul George was not where he was in Oklahoma City. And it just didn't work. Los Angeles is a city that loves stars, but they like winning.

And we're a fairly front running place, except for the Dodgers. And so it just wasn't working on. It's been years of frustration for the clippers. I mean, they had three big stars in Lake Griffin, in the center. And it just never quite worked for them. And they have a problem in that they're a little bit in the shadow of the Lakers.

Oh, without a doubt. Now, I know Uncle Dennis, I'll call him Uncle Dennis. This is Dennis Robertson, but he was Kauai's uncle, obviously, and business manager. And I remember all these reports about demands Uncle Dennis was making on behalf of his nephew. So you, Lee Steinberg, as a super agent representing these superstars, if your client is asking for things that might circumvent the salary cap, and cause the issues we're seeing. Now, like, how do you tell your client,

no, you can't ask for that? Well, you point out the settlement in the Lai-Clipper-Lylander situation, and that the team may be able to agree to something, but it doesn't mean that it will last and it may put the player in jeopardy, or at risk himself. I mean, to an ordinary person a $700,000 fine is mind-boggling. Obviously, star NBA players make a fortune.

So you point out that past examples of where even if you could get a team to agree to something, then ultimately you'd be waiting for the other. shoot a drop if at some point everything becomes public. Because you make a great point that for the amount of dollars that Kauai Leonard got beyond the salary cap during his term with the Clippers, like $700,000, and I'm sure you can speak to why it's that number, but that's not a very severe punishment for Kauai Leonard himself. I think they needed the NBA Players Association. to sign off on the penalties or wanted them to be part of this.

And they were very protective of Kauai. Now, you know, this is Toronto-Miked, and I'm speaking to a primarily greater Toronto area audience, and most of the listenership right now are Raptor fans and the inherent bias there. But when I look at, you know, we're the only non-American team in the NBA. and we know Kauai brought the championship. He helped bring the championship here in 2019,

his one and done year here. And then we trade this, what I think was a huge package to bring him back. He's 35 years old, Kauai, even though he's coming off a great year. And then suddenly the NBA is like, not so fast. And now this entire saga has been

unfolding here. It doesn't feel, to me, it doesn't feel fair to Toronto, Ontario, Canada, and the Toronto Raptors franchise? Well, remember that they're like a bystander to everything happening in Clipper Nation. They're not involved. No one has made any allegations against Toronto's.

Their judgment that he is so dynamic and so transformational that he was worth all of that. and I mean, people may have mixed feelings, but the first time he hits a triple double, he'll be Toronto's favorite again. Good point. So what do you, and I was going to save this for the final question, but I got to ask it right now is,

as we speak, and I got to timestamp it because, I mean, things could change in 10 minutes here. But as we speak, this trade is still not official. Do you have any insight, any idea what the holdup is? Well, I'm sure the trade will become official, but this deal was just made and it's probably still being papered. And once it's done, I'm sure the trade will be approved. And I mean, Toronto's a great sports market.

I mean, my beloved Dodgers came very close to losing. So the fact that you have a World Series baseball team, and I had a good time years ago with Ricky Williams with the Argonauts. And he loved it up there. He said that he would have played forever if he could have played in Toronto and the CFL. But it is worth noting that this franchise started in 1995 and now we're talking how many years later, 2026. what is that, 31 years or whatever that is. I got to do better math here. But I do note that no top-tier NBA free agent ever chooses to sign in Toronto.

Like, it's worth noting Kauai will now be hopefully a two-time Raptor, and both times we needed to trade for him. I think the biggest free agent signing, believe it or not, is like he do Turko-Glu. Like, I don't think there's ever been a top-tier free agent who said, I'm signing in Toronto, unless they were already. Radioraptor? Then probably the teams have to do a better job of showing the player of the city and understanding all the benefits and advantages that you get from being in a sophisticated metropolitan area

like that and showcased it. I mean, I haven't checked on the differential tax treatment yet. and what effect that has on valuing money. But like I said, from my perspective, Toronto is one of four or five great metropolitan areas. And it basically is geographically very close to the United States. and incidentally Mike don't blame everyday Americans for the policies of our government I'm glad you brought that up only because we're you know mired in a trade war right now

we love everybody you know loves Canada loves going there loves the Canadian people thinks they're amazing but you know I don't control the government at this point you can say everybody there loves Canada except the president

yeah but it's like it it's sort of amazing because Canada's always been the U.S. as closest ally were

you know cousins from the same revolutionary situation. And people in Canada, by and large, are really nice. And it's a great experience to interact with them. It's the solemn anniversary of 9-11 coming up this week. And I remember that many Americans were not able to fly because there was no commercial flights allowed that day. And us Canadians took Americans into our homes and fed Americans

and took care of Americans like they were Canadian during that terrible, terrible day. And fought with us in World War I and fought with us in World War II. And it's always been supportive just as a citizen of one. country to another, let me tell you, this is not something that most Americans are excited about. I would like to go back to the way it was. Well, I'm glad you're saying that, Lee. It makes me feel good to hear you, hear you say that. So just to get back to Kauai Gate or whatever we're coining this saga here, but this

coming down hard on the clippers and Balmer, and devastating the franchise with those first round picks they're going to lose. Do you think now this message has been received by every superstar in the NBA that you can have enormous power but you can't dictate the financial architecture of this league? Resounding, yes.

It's, I mean, to lose five first round traffics, you know, the $30 million dollars can be afforded by a billionaire, but it's, and they've spent what at that time was the record $2 billion for the franchise and now be suspended for a year. And Steve Bomber, with forgetting what happened in Kaua, his situation, has been a popular and great owner of the team, willing to do whatever it takes to bring a winner. That franchise seems cursed somehow. It's had an interesting background.

I mean, for the years in which they had Chris Paul and Blake Griffin and still couldn't, and a really good center, and still couldn't make. take it. But it's, that's an interesting background. It started in Buffalo and then moved to San Diego. And then they were talking today about what the derivation of a clipper name is. Why the clippers in Los Angeles? Well, why the jazz in Utah? That was the same point that the fellow I was listening to. That's true, right? Even Calgary Flames, okay, in our NHL here, that was because Atlanta's fire, that was the Atlanta Flames.

Well, sadly, there have been too many fires in Canada. Well, I was going to point out with that 9-11 reminder of how Canadians helped America that when there are fires in California, you know, we sent over our, you know, just we sent over, I don't know what you call them, the people who have the water planes, They scoop up the water and they help put out these fires. And I think when we had fires here in Ontario, your president basically went out and said he was going to tariff us. I think he did.

Tariffed this country because of the pollution that was crossing the border. So there you go. I know enough politics, but go ahead. Yeah, my reaction to the Canadian fires is to have empathy and sympathy and support for them. And this situation won't last. I mean, it will normalize again because the majority of people want it to be like it was. All right.

So we're winding down here. We only have the half hour here. But if we went back to 2019, Lee, I know we're going back to 2019. I like to live in 2019 as a Raptor fan, to be honest. But if we go back to 2019 and Kauai Leonard walks into your office and he says to you, I want to control where I play, who I play with, how I structure my business. What would your advice have been to Kauai Leonard in 2019? As I said, to do an internal inventory as to what priorities are really interesting.

For some people, it's just money. For some people, it's the ability to win a title and get to an NBA championship. For some people, it's the quality of the coach or the teammates. for some people it's geographical location. It's being able to live in a certain market with a certain lifestyle. So the first step in that would be to prioritize what really is more important. It's not different than a young kid going off to college. And this campus has better dorms and this one has better athletic teams.

and this one has smaller class size and this one. And what happens, you're trying to clarify the thinking process. So cognitive dissonance, the tug between multiple poles, doesn't overwhelm someone and force them to make a decision. So decision making that's reflective of his individual values is what I would emphasize. but I think it, except for the fact that it didn't produce championships in Los Angeles, it's worked the way he wanted it to. Okay, last question, Lee, and again, thank you for your time today.

This won't be the last time we talk. It's pretty awesome I get to connect with the man who inspired Jerry Maguire. Okay, that's not an everyday occurrence, so we'll talk again. But so I mentioned the dates off the top and the most. recent date of significance is September 2nd, because that's the day this investigation was completed and the NBA announced the penalties, those enormous penalties. And then I asked you already in this conversation, like, why hasn't this deal been gone through yet? Why isn't it finalized? And you mentioned, you know, it's, because we're a week out.

Is there any possibility either the clippers or the raptors are trying to change this deal? Like, is there any possibility that one party wants to try to get more or get less, or, you know, give less? Like, I'm wondering if that's possibly the hold up here. If it is, I don't have any knowledge of it. And I would assume the trade will go through as originally negotiated. And do you have a prediction? I know the crystal ball might be a little blurry there, but, The 2020, 627 Toronto Raptors with Kauai Leonard back, how do you think the Raptors will do?

They're going to be good. And, you know, they're going to be good. You know, you've got the Knicks and the Thunder and a variety of good young teams, but they'll be excited. They'll be fun to watch. They'll score a lot of points. They'll do some razzle-dazzle. be entertaining.

Well, Lee, thanks again for your time today, my friend. You're an FOTM, a friend of Toronto Mike, and again, we will talk again. Nice talking to you. And that brings us to the end of our 1,9th show. Go to trotomike.com

for all your Toronto mic needs. Much love to all who made this possible. That is Great Lakes Brewery, delicious fresh craft beer. I can't wait to see everybody at TMLX 23 on September 28th, 2026 from 6 to 9 p.m.

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