Uncover - S39 E2: The Boss | The Most Wanted Olympian

Episode Date: October 15, 2026

Former federal agent Brett Kalina is one of only a handful of law enforcement officers to come face to face with Ryan Wedding. In 2008, after years following the flow of money and drugs, Kalina arrests ‘The Boss’ and watches as the ex-snowboarder goes to trial.But once behind bars, Wedding turns the tables. He makes prison work for him, using his time inside a violent Texas detention centre to allegedly make criminal connections and cartel contacts. And the next time the police come looking for him, he’s already gone. This podcast is a co-production of Uncover from CBC and Suspicion from the Toronto Star.

I've been staring at my offer letter for three days. The salary is exciting, but trying to understand terms like group matching and flexible spending, it feels like reading another language. Congrats on the job. That's huge. But yeah, entering a new workplace comes with a big learning curve. I just want to make sure I'm setting myself up right from day one. It feels like there's so much to figure out about how all of this works. We all feel a bit out of our depth when starting out.

When I made my last jump, I was totally trying to make sense of my new paycheck and my real-life expenses. Glad, it's not just me. It helps to know that everyone goes through this phase. For sure. Honestly, just bringing it up in the first place is half the battle. Landing the job is just the start of the journey. Want to hear how others are navigating the early careers? Check out Count Us In.

A web series where host Michelle Spina sits down with members of Gen Z to share real perspectives and experiences on money, and what comes next. Paid content with Desjardin. Now streaming on CBC Gem. This is a CBC podcast. It's December 2008 at Reeves County Detention Center in Texas, and a riot has broken out. The United States prison system is notoriously overcrowded and often violent. But even among the worst scandals and uprisings, the riot at Reeves stands out. At the time, it was the world's largest for-profit prison.

An inmate, Jesus Manuel Galindo, have been telling prison staff that he wasn't receiving the proper dosage of his seizure medication for his epilepsy. He told his family he was worried. He even wrote to the warden. On the morning of December 12th, his body was carried out of solitary confinement

in what looked like a garbage bag. When inmates see that, all hell breaks loose. By that evening, a delegation of seven inmates from Venezuela, Cuba, Nigeria, and four men from Mexico meet with the authorities to protest Jesus' death and state their demands for improved conditions. Chief among them, better medical care. Authorities say they will do better, but little to nothing changes.

A month and a half later, the inmates riot and again are in control. What started out as a prison riot in Reeves County has now turned into a public relations battle. That's right. Earlier today, the inmate started another wave of phone calls to KMID and its reporters. We want better treatment. Food. Three people have died in the past six months. We had another riot back in December. For the same reason, this guy died for negligence. This time, the riot lasts for five days and ends with $20 million in damages. The unrest continues for years, and this is the scene that greets Reeves' newest mate, a Canadian, former Olympic snowboarder, Ryan Wedding.

You may think the odds are stacked against him being trapped in this hostile environment. But by all accounts, Wedding doesn't just survive. He thrives and makes prison work for him. I'm Michelle Shepard, and from CBC Podcasts and the Toronto Star, this is the Most Wanted Olympian. Episode 2, The Boss. Do you remember the first time you would have heard the name Ryan Wedding? Ryan was not known to me until he stepped off the plane in June of 2008.

Brett Kalina is a former FBI agent who retired after 20 years. He entered the agency after 9-11, working everything from Mexican mafia squad to helping investigators on the horrific mass shooting at Paul's Nightclub. a gay bar in Orlando, Florida. In June 2008, Brett was nearing the end of a money laundering-turned drug smuggling case. The investigation had been going on for nearly two years. One of the targets was a Russian-Canadian, a Vancouver businessman named Michael Crapchan. We knew him not to be a big player, but he was our conduit.

And we knew early on that Crapchan certainly wasn't the leader or the head of any type of organization. So Brett keeps watching Crapchan to see who he's dealing with, to get at the higher-ups. This is often how it works in organized crime investigations. Use a small fish to get at a bigger one. The FBI only knows Crapchan's contacts by their code names. One of them he calls the boss or the big guy. When a plan is made for Crapshan's contacts to come to Los Angeles, Brett is part of the surveillance team at LAX, covertly waiting for them to arrive. They've got a man on the inside, too.

An ex-KGB agent turned FBI undercover source. The source goes with Crabtan to pick up the men from the airport. And he gets a lucky break. Because when their luggage comes down the carousal... These guys had bad tags, and the source was good enough to either... get a look at it or a quick snapshot of the bag tags with their names on them. So now the FBI has two new targets for their drug investigation,

a Canadian of Iranian origin and a very tall white guy whose bag tag says Ryan Wedding. This is the man who Kalina says was called the boss. We were looking at a totally different organization in Vancouver at the time. Well, these two individuals had nothing to do with that group. So you think you're going one way in the investigation, and then these two new people show up, and you don't really know what you have at that point? Yeah, not a favorite operational plan of the FBI to just go in blind. It's pretty rare that we would do those types of things.

So with their new suspects identified, a sting is planned. The FBI's undercover source will pose as a... the cellar, waiting to see if wedding and his associates will buy cocaine from him. In cops speak, this is known as a reverse buy. It takes a couple days for everything to be arranged. As wedding and his crew wait, they go shopping, smoke hookahs at cafes, and meet at a Denny's to discuss the details of the deal. Finally, everything is in place. The FBI's trap is set. Wedding goes to the hotel where Michael Crapchan is staying. He gives Crapchan the keys to their rental car so he can go buy the drugs.

And then he waits. And then they sat and were in the room the entire time. And coincidentally, they didn't even bring, they didn't have a key to Crabtzhan's hotel. So they stayed in the room and they realized they couldn't leave because they didn't have a key. So we knew that they had to stay in the room. Court testimony will later allege that during this time, Wedding took a nap. Meanwhile, the first part of the drug deal is underway.

Krapchan buys a kilo of cocaine from the FBI undercover. And then when Krapchan came, the deal happened very quickly. The source asked Krapchan to contact Wedding and let him know that he had. the product. And that wedding would be on the hook for saying, yes, okay, great, bring that kilo back to the room. With that evidence in hand, the FBI arrests crap chan. And wedding? He's next. And that's when we went to the hotel. We had this huge group of people. We had two SWAT teams out there because we had a lot of cocaine. As I was approaching the door to knock on the

door, they had just opened up the door to leave. I think they'd gotten nervous that it had taken Crapshanon so long to come back and we're finally going to leave. That's quite a scene. I can picture it. You know, you're about to knock and then the door swings open. You're like, oh, hi. Yes. It was. We were actually getting pretty nervous that they would try to take off because of the amount of time. And I also wanted to be there as the case agent to make sure that I was there to have that first conversation with wedding. And what was that like that first conversation? There wasn't a conversation. Wedding said, well, I don't know what this is for.

You know, I don't know what you guys are talking about. he said something to the fact of, well, I'm not going to talk to you. And so he was very quiet, at least at first. He wasn't necessarily argumentative or fighting. He just kind of held out thinking like, these guys have nothing. I'm not going to worry about anything. And took that posture pretty early on after we arrested him. Did that ever change or was he like that the whole time?

It only got progressively more amped up as we went along. He got angrier, more vocal. So the day's getting long. He's not happy to be in handcuffs for hours on end. And having someone as diminutive as me compared to him, you know, kind of bossing him around. And my partner at that time, who also helped me with the interviews as a female, He thought he could use his charm on her, which was comical at times. But obviously that never worked and just made him matter.

Is that kind of belligerence typical with suspects that you've arrested over your career? Not at all. He was very unique in that you usually get someone who'll say, you know, what is this for? I have no idea. Try to just feign that they know anything about why they might be arrested. But they're generally not either belligerent or angry because they know you're holding their life in their hands. As wedding is being processed, Brett is with him every step of the way.

I had to be there while he was changing into his new clothes and getting searched. And I'm there watching it. And he just yells at me to stop, calls me. a faggot and just stares me down. Wow. Really hostile. Very. He just wanted to assert his dominance. You know, it felt like, I don't know, you know, it felt like, you know, a kid on a playground, right? They just, they're, they're backed into a corner and the only thing

they know at that point in time is to use what power they have left. That confidence, the swagger, it also applied to those wedding was keeping in touch with, mainly women. As he sat in a San Diego jail awaiting trial, he would talk to them by phone asking for favors, phones that were being listened to. Hey, can you go take this package? Can you go pay my electricity bill? Can you go pay my rent? To all these different people, they were just people that did things for him while he was in jail. And they never obviously came down to meet him, but there was always the idea that, okay, I could be the last one when he gets out.

It doesn't sound like he's particularly charming. I wonder if it was just the prestige of being a Olympic snowboarder and the, I don't know, the badness of being in jail. It wasn't that he was necessarily cruel or, you know, talked down to these people when he was on the phone with him. He was nice with them. and never did anything that made you concerned that there was other things going on between them.

I just think he was a big player in Vancouver. He just had some clout. So while Wedding was using his clout to keep his lights on and bills paid on the outside, inside he's making new connections. Because he's locked up in a pretty diverse place with a lot of people passing. through. This is the one federal lockup. So everybody that's getting arrested at the border for

bringing something across, everybody that's getting arrested by customs for not having documentation. And that's the entire holding facility until sentencing. And you're talking about high-level individuals, individuals that have been arrested by federal law enforcement. It's not a nice place. It does sound like someone used the phrase, you know, a graduate school for criminals. If you do go in there and are guilty, you could come out with a higher degree from the contacts you meet. Yeah, we knew from listening to his calls that he was making contacts. Not only was he meeting some people, I am sure he was getting legal advice or what he thought was legal advice, getting information about the process, not just legal, but how those other people were in there

and how they got caught or what they might have done wrong to be in jail versus getting away with it. And so he was learning quite a bit. After almost a year and a half in pretrial custody, Ryan Wedding heads to court to try to apply whatever legal advice he's just learned. He's charged with conspiracy to possess and distribute cocaine. The minimum sentence for a crime like this is 10 years. The maximum is life. I almost bailed on brunch this morning.

I opened my banking app before leaving, saw a few unexpected expenses, and just felt that instant wave of stress. I hear you. Money stress is real and it's exhausting when it feels never ending. Yeah. It feels like every time I get a handle on things, three unexpected bills hit it once. I'm just trying to get to a point where managing money doesn't feel so overwhelming.

Honestly, just being open about it helps take away some of that pressure. You're definitely not alone in feeling that way. Thanks. It really does help to just talk it through and hear how other people are handling it. Money is a big part of life, but you don't have to navigate the conversation alone. If you're looking for real stories, an open dialogue, check out Count Us In. A web series where host Michelle Spina sits down with members of Gen Z to share real perspectives and experiences on money, life, and what comes next. Paid content with Desjardé.

Now streaming on CBC Gem. This ascent isn't for everyone. You need grit to climb this high this often. You've got to be an underdog that always over delivers. You've got to be 6,500 hospital staff, 1,000 doctors, all doing so much with so little. You've got to be Scarborough. Defined by our uphill battle and always striving towards new heights. And you can help us keep climbing. Donate at lovescarbro.cairbo.ca.a.

On November 16, 2009, the trial against Ryan Wedding begins. Brett Colina, who testifies at the trial, remembers that Wedding's mother and one of his sisters that come from Canada to support him. The stakes are high. He's facing a possible life sentence. But wedding seems unfazed. At one point, the judge threatens to charge him with contempt. He's caught passing notes to his sister.

One of the intercepted notes reads, See you soon, dear. Ha ha, ha, miss you, love you, Ryan. All work and no play makes Jack a dull boy. All work and no play makes Jack a dull boy. He was so arrogant. He really thought he was going to get off. He just assumed that somehow he could convince the jury or the judge that all of this was just a deal made up by Crapchan and he's taking the fall.

But that wasn't looking like the case. Well, it didn't take long for Crapchan. to agree to testify against him. Even so, Wedding's confidence doesn't seem to waver. We knew that from his phone calls. He was very confident that he was going to walk out of their free. Wedding's defense positions him as innocent, a good Canadian boy from a stable family, an athlete, a former Olympian.

Wedding, his lawyer tells the judge, had just made some mistakes, that he came on a trip to California for fun and a bit of business. to take a look at properties that he might be interested in buying. He was pulled into the drug deal, not the one who arranged it. His relatives provide statements speaking about his athleticism and discipline and note how family-oriented he is. But it's not enough. When recorded conversations between wedding, his crew,

and the FBI's confidential source are played in court, his defense just doesn't hold up. On the 30th of November 2009, the judge, jury is discharged to deliberate. They returned after just two and a half hours to find wedding guilty. When he is sentenced six months later, Brett clocks a very different demeanor in court. He was defiant up and through trial, and it wasn't until sentencing that he all of a sudden admitted, okay, maybe it made a mistake here, but I want a second chance.

I want to go back to my life of snowboarding. that type of thing. Wedding reads a statement at his hearing. All right. Well, I prepared something just in case I got tongue tied up here. We don't have the audio of the court proceeding, so I've asked a colleague to read sections of the transcript. I would like to apologize to the court, to the government, and to my amazingly supportive family

for the stupid and irresponsible decisions that I made that resulted in me coming down to San Diego to buy drugs. In the past 24 months, spent in custody about an opportunity to see firsthand what drugs do to people. And honestly, I'm ashamed that I became part of the problem. Your Honor, what I did was completely out of character for me. And it is a personal mission of mine to rebuild my reputation. And I'm actually looking forward to incorporating some of the things that I've learned

over the last couple of years into my daily life. As an athlete, I was always taught that there was no second chances. And well, I'm here asking for exactly that. The judge seems somewhat sympathetic to wedding, but he's not letting him get out of jail free. He sentence his wedding to four years. It's not anywhere close to the 10 to life he could have gotten. But it's not nothing. The judge may have bought wedding's contrition, but Brett, he didn't.

He was never sorry for what he did. It wasn't a mistake. He knew full well what he was getting into. He just didn't think he'd get caught this quickly. And that's when wedding is sent to Reeves County Detention Center in Peacost, Texas, the sprawling immigration prison where inmates had been rioting. Being a Canadian snowboarder in a Texas jail means absolutely nothing. Being a white Canadian, you don't fit into any of the groups that are already there.

So you have to tow the line, you have to be quiet, you have to do things. things under the radar. You just don't want to stick out, especially for someone in that position who just wants to get back to Canada. You just want to go under the radar. And so he presumably did a pretty good job of that, but at the same time, he was clearly making contacts.

Do you think he was making cartel contacts at that time, too? It's hard to tell. I suspect so, but I don't know for sure. You know, once the trial's over and he's been convicted, it's not as easy for us to maintain that same type of surveillance over somebody because we don't have a reason to do so anymore. There may not be surveillance, but there is a paper trail documenting one connection wedding made in prison, dated February 14th, 2011.

It's his wedding certificate. Nine years to the day, after his Olympic performance, he's about to put another Valentine's Day anniversary into his calendar. I first learned that there was a wife, that there was a partner in the picture around the time that wedding was in jail through his source, and I wasn't given much to work with. Toronto Star reporter Calvillian again. I was told that you should look into his wife. This is what your source is telling you, but not directing you. exactly where to find this information.

Correct. And so I just did some digging. I was looking into different names that had surfaced in court documents from his previous drug offenses. A little digging online and she finds someone on social media who is probably her. So Calvi reaches out. And I just said, hey, this is who I am. This is how I found your name. It lists you as being married to Ryan Wedding in 2011.

Can you confirm this? Would you be open to chatting? here's my phone number. And then from there, we went back and forth. We were messaging for several weeks, and she actually answered multiple of my questions. She tells Calv that, yes, they had a prison wedding, and she confirms that they lived together briefly when he was later released from prison, but that their marriage was short. CBC journalist Thomas Daigle also interviewed the woman, who said she believed wedding was innocent and wrongly detained.

You married him while he was in prison. Didn't you have many? concerns about his lifestyle at the time? No, he said that he was just there with a friend and he got convicted, like he was just at the wrong place and wrong time. There was one other Canadian who we know was incarcerated at Reeves at the same time as wedding. His name is Jonathan Asabeto Garcia, John to Friends. He's a dual citizen of Columbia and Canada and grew up in Montreal.

Before he was caught, he was getting by as a low-level drug dealer in the U.S. But one day, while driving in upstate New York, he was pulled over by state trooper for speeding. He was also carrying 23,000 ecstasy pills. Like wedding, he was sent to Reeves to serve his sentence. On December 7, 2011, wedding is released, a little early due to good behavior. He's handed over to ICE, U.S. immigration, and customs enforcement, and sent back to Canada. His friend, Jonathan, would spend another 11 months in Reeves before also coming back home. Wedding and Jonathan both end up in the Montreal area, and the pair would

stay in each other's lives for over a decade. It's hard to know the full details of what wedding was doing after his release, but court documents fill in some gaps. In 2014, wedding files for bankruptcy, saying he was more than $670,000 in debt. And despite his pledge to the judge that it was his personal mission to turn his life around. It appeared to be turning in other ways. RCMP seized cash, guns, and more than 250 kilograms of cocaine. Transactions were made at sea and the drugs continued on to cities in California, Texas and Florida, as well as Toronto, Montreal, Halifax, and St. John's. In the spring of 2013, the RCMP received a tip that someone in Canada was attempting to import large amounts of cocaine

from South America into Nova Scotia. That launched an undercover sting operation that led from one target to the next and would expose a web of accomplices across the country and beyond. The RCMP called it Operation Harrington. I think it was in total. There was 15 suspects for eight separate conspiracies.

It was conspiracies touching on St. Kitts, Antigua, Guyana, Colombia, all sorts of other places. Journalist Brian Fitzpatrick extensively covered Operation Harrington and its fallout for the National Post newspaper. So Operation Harrington was a RCP sting, if you want to call it, into a number of different cocaine importation conspiracies

dealing with individuals who were moving cocaine from Latin America north into the eastern seaboard of Canada. It's a hell of a suspect list. A Canadian Department of National Defense contractor, someone who works with the Coast Guard, a real estate agent, a trucker, a guy who runs a Peter restaurant, and is a beloved high school volleyball coach.

And there's Philippos Caleros. Caleros was originally from BC. he was living in Montreal in a downtown condo. He was known to police as a drug trafficking guy connected to Greek organized crime and also listed in documents that I found connected to the Sinaloa cartel. He was also connected to Ryan Wedding. They both lived at apartments that were super close to each other.

Do we know how they met each other, Clarice and Wedding? We don't. We don't know exactly. how, you know, but these things are super fluid. A lot of these people just tended to fall into the same circles. It's, although there's a lot of people importing cocaine in Canada, there's probably not that many in between Toronto, Montreal, Ottawa, on a scale like this. So it seems they all kind of either knew each other or knew of each other. So everybody's a friend of a friend, probably. Yeah, to a degree among these guys for sure, you know, they definitely, they had that six degrees a separation thing going on.

Court documents suggest wedding and Caleros were tight, and there was a wider network building. You know, it does seem that those connections were kind of made pretty quickly. His friend there, Calaros, had been spotted in Montreal with the wife of Alex I Fuentes Villa, who was basically the right-hand man of El Chapo. Yes, that El Chapo. the former head of the Sinaloa cartel. His right-hand man, who sometimes was known as Alex El Chapo, would move freely between the mountains of Mexico and Montreal.

That's where he's allegedly rubbing shoulders with Caleros and his friend, Ryan Wedding. It's very clear that the main players, or some of the main players, they were all in different ways connected to the Sinaloa cartel. Operation Harrington lasts two years until finally at the end of April 2015, the RCMP makes their move. Over three-day blitz, they arrest nine suspects facing charges of importing and trafficking drugs and weapons. Warrants are issued for another six accused who can't be found. Among them, 33-year-old, Ryan James Wedding.

How did he slip through the net of Harrington and not get arrested at the end? he may have been tipped off and decided to, you know, make a break through at that point. Ryan Wedding was never apprehended and was kind of never seen since. So if he was such a big deal, how did he get away? And where did he go? Like, it's easy for a guy like Ryan, no matter how tall he is, to blend into these neighborhoods. And given the level of corruption here in Mexico,

no one is going to toadge a hair of this man. But now things could change because, you know, he's in this boat lie right now. That's on the next episode of the Most Wanted Olympian. This podcast is a co-production between CBC podcasts and the Toronto Star. Our series was written and produced by Phelan Johnson, Calvie Leon, and me, Michelle Shepard. At CBC, Emily Connell is our coordinating producer. Our senior producer is Andrew Friesen,

mixing and sound design by Evan. Kelly. Executive producers are Cecil Fernandez and Chris Oak. Tanya Springer is the senior manager and RF Narani is the director of CBC Podcasts. Additional audio from KMID, Texas. For the Toronto Star, Calvi Leon led our reporting. Our producer is Julia DeLerentis Johnston. Team editors are Sean Paddenin and Ed Tubb. Keith Pinell is Deputy Managing Editor. J.P. Foso is our executive producer. And special thanks to executive editor Grant Ellis and editor-in-chief Nicole McIntyre.

Tune in next week for an all-new episode of the Most Wanted Olympian, or you can listen to the full series now by subscribing to CBC True Crime Premium on Apple Podcasts or by subscribing to the CBC True Crime channel on YouTube.

Links in the description. For more CBC podcasts, go to cBC.c.ca slash podcasts. Thank you.