Inside the wild, star-studded sale of the Ottawa Senators

CLIP You are listening to a Frequency Podcast network production.

Jordan Heath Rawlings This story begins all the way back at a Stanley Cup finals game in 2007 between the Anaheim Ducks and the Ottawa Senators, and it’s still a legendary tale today.

CLIP Scott Oak: Welcome to Hockey Night in Canada. One of the world’s great contemporary musicians, the dog father, D-O-double jizzy. They got some this front planet. What’s crackling nephew? Snoop Dogg: Hey, hey. What’s up?

Jordan Heath Rawlings That hockey night in Canada interview between reporter Scott Oak and Rapper Snoop Dogg went viral in an era before the term was common. And it turned out that what Snoop said next, would predict a saga that would unfold more than 15 years later.

CLIP Scott Oak: What’s got you into hockey? Snoop Dogg: I love the way they move up and down the, you know, the ice with intensity, speed, the action. I’m just a fan of it. I love it every minute of it. Scott Oak: Know you played Ottawa a while ago and Ray Emery gave you a senator’s sweater. Did you think about wearing it today? He’s been playing great, by the way. Snoop Dogg: He’s been playing great, but I couldn’t wear it here tonight. I’d be barbecued if I wore that jersey in Anaheim, but I’m supporting him in the whole, you know, national Hockey League, Stanley Cup. I’m happy to be here. It’s a beautiful thing.

Jordan Heath Rawlings So a decade and a half ago, Snoop Dogg was a Ray Emery fan rocking the Goalies Ottawa, senator’s Jersey, though not in front of the hometown Anaheim crowd. And today he is a part of a group that’s trying to buy the whole Ottawa team, and he has promised publicly that he is more than just a big name attached to the project for fun. He says he’s all in on Ottawa and he is not the only megastar fighting over this hockey club. Somehow someway, the bidding process for the sale of the Ottawa senators has become the most star studded right out in public bidding process that anyone in the business of sports can remember. Nobody knows how it ends and here’s the inside story.

I am Jordan Heath Rawlings. This is The Big Story. Elliotte Friedman is a hockey insider with SportsNet. You’ve probably seen him on Hockey Night in Canada. If you’re smart, you’ve heard him as the co-host on the 32 Thoughts Podcast. Hey, Elliotte.

Elliottete Friedman I like the way you promoted, that’s very kind of you.

Jordan Heath Rawlings Well listen, we’ve got a sports business, slash Hollywood story I guess to get to today. But let’s start with the sports business cole’s notes, the Ottawa Senators are for sale. Why are they up for sale? How did we get to this point?

Elliottete Friedman Jordan, they are up for sale because the previous owner of the Ottawa senators, Eugene Melnyck, who’d owned them for around 20 years. He passed away in the spring of 2022 and as a result, his estate put the team up for sale. Now, his two daughters, Anna and Olivia, it is believed that they will, would like to keep a small percentage of the team somewhere around, five to 10%. But after, Eugene’s death, the team became available on the market.

Jordan Heath Rawlings So before we get to the bids themselves and like where we’re at in the process, you know, the reason we’re doing this episode is because this franchise has attracted a lot of attention. I guess my question is, when the Ottawa senators went up for sale, you know, how attractive a proposition was it thought to be? Maybe I’m wrong. I certainly didn’t think we’d be talking about this many bids, all these stars involved. Like it’s the Ottawa senators, right?

Elliottete Friedman Well, I think what it is, Jordan, is that. Let’s just forget about the sports aspect of it. Take a look at business. If you go back through the last 30 to 40 years and you take a look at the value of sports teams, they’ve gone up. They’ve gone up a lot. And at times there’s been questions about is there going to be a bubble? Like right now we’re talking about the regional sports network bubble, and there are challenges in the worlds of sports business, like there are challenges in any business. But I was born in 1970 Jordan, and if you take a look at the value of teams from 1970 to 2023, there is no question, the return on investment of them has been very good. And one of the things, did you ever see the movie about Ray Crock, the founder of McDonald’s,

Jordan Heath Rawlings Right. Yes.

Elliottete Friedman So there’s one scene in that movie where, and, forgive me if I’m not quoting it accurately, but they basic, he’s basically asked, what are you? And he goes, I sell hamburgers. Yeah. He says, and the person says, no, you’re not. You sell hamburgers. But that’s like a disguise for a real estate company. And like a lot of these teams, if you take a look at the real estate that comes around them, and real estate is a very big part of the Ottawa Senator sale. It’s not only the team and the teams are growing in value, but so is the real estate around them. And some of the things that come with it, for example, until recently, regional sports television, it’s a good investment. And that’s why people are interested.

Jordan Heath Rawlings But all that makes sense from a business point of view for, you know, millionaires, billionaires, investing in a team because, hey, listen, it’s, it’s gonna turn a profit almost, for sure. Tell me about what’s unique about this bidding process, though, in terms of just like the star power that it has attracted, not maybe leading the bids but associated with them.

Elliottete Friedman I think it’s a great question. So let’s look at three of the biggest names. Okay, so number one, everyone’s talking about Ryan Reynolds and everyone was very excited about Ryan Reynolds. Well, Ryan Reynolds took an initial four A into sports with Wrexham Football Club and it, and it’s been a fifth deck home run for him and the organization. Like Ryan Reynolds, not only is he a talented thespian, he is a very talented investor and business person. And I think you’ve seen almost anything he touches, he knows how to market it and he knows how to make money off of it. And so, you know, when you get that much adulation, he’s probably had more adulation for what he’s done with Wrexham than he has for maybe any of his acting roles. Whether it’s Deadpool, Green Lantern, Van Wilder or any of the other things he’s done, this has probably brought him more accolade than any of that. So you get that and you want more. Plus he’s obviously got the Ottawa connection, and when you have someone on Ryan Reynolds level who comes in and says, this is cool and I want to be a part of it, it attracts other people who look at it and say, you know what? This is cool. I want to be a part of it. And also as we’ve seen in this part of business too, is that other people say, oh yeah, you know him well, I know him, and now Snoop Dogg is on ESPN first take, and The Weeknd is part of one of the other bids now. I think that cool attracts cool, and because Ryan Reynolds has made this look cool, other people want to be part of it.

Jordan Heath Rawlings We’ll talk about Snoop in The Weeknd in a second because they are part of the active bids. Before we talked over The Weeknd, the Ryan Reynolds bid appears to have backed out. What do we know about that bid and, and why didn’t it go ahead. And I guess from your perspective, because you cover this a lot, how common is that in this process?

Elliottete Friedman It’s common all the time where people kick tires or are involved and then don’t make a bid. That’s not unusual. This one was, was different. Like there’s a lot Jordan to unpack here and I’ll try to help you do it the best I possibly can. With this particular bid, he went in with a group called Remington, and let me explain who they are. Remington is owned by the bratty family, B-R-A-T-T-Y. For those of you, like I live in Toronto, one of the areas just north of the city is an area called Vaughn. When I was a kid, Vaughn was a wasteland. There was nothing there when I was in grade 13, and that’s how old I am because grade 13 doesn’t even exist anymore in Ontario. My family moved from North York to Thorn Hill and it was still a lot of nothing there. This was 1988 and I remember the first time my friends came up to my new, our new house to play cards, they all brought their passports as a joke, like there was nothing there. And Vaughn is basically adjacent to Thornhill. They built Vaughn. He’s in his nineties now, I believe. But the leader of the family was Rudy Bratty, and my father used to be in the construction business or the development business, he corrects me.

And everybody knew Rudy Bratty and Rudy Bratty put fear into people, what he wanted he got. He was a very strong, powerful, sharp businessman. Well he’s older now and his children have taken over and years ago they almost purchased the Arizona Coyotes and they backed out late, late, late in the process because they didn’t like the real estate deal. And that bothered the NHL at the time. They were really upset. So anyway, when this became available, and again, like we talked about earlier, real estate is a very big part of this sale and what you’re gonna be able to do around the projected new arena and what you could do with the current one. Like they were interested because that’s what they do, they build. And Ryan Reynolds had met with the NHL and I think what happened was, I think the NHL wanted Ryan Reynolds to stay neutral. I think they said don’t join a group. And we will place you with the winning group. And Ryan Reynolds made the choice to join this group. And very recently with the bids due this week, they asked for an exclusive window and they were rejected. And when they were rejected for that, they said, we’re not going to bid. And you know, I checked with some people who know this world better than I do, and they said that the NHL, the bankers and the Senators were right not to allow the exclusive window.

And I said, why not? And they told me, because you don’t know if they’re gonna have the biggest bid, you have a responsibility. It’s called a fiduciary duty, legal responsibility, to see all the bids. So you know if one is greater than the other. If it turned out that you gave them an exclusive window and someone was willing to bid the same as them or more, you didn’t do your proper duty for the sale. Especially because there’s creditors here. There’s some debt right now. There’s some hard feelings. I’ve heard. I haven’t spoke to him, but I’ve heard Ryan Reynolds is upset and the NHL is not going to win a public PR fight with Ryan Reynolds. But I think the NHL feels, you know, Hey, we warned you this could happen. You shouldn’t have done that. So we’ll see how it all plays out. Like people have told me this is dead. It’s over. Ryan Round’s not gonna be part of it. Jordan, I’ve been around long enough to know that you can be mad at somebody one day, but if there’s a marriage of convenience a week later people find ways to do things. Let’s just see what happens when this is all over.

Jordan Heath Rawlings And in the meantime, there are a few bids that did make the official deadline. Can you just briefly outline what those bids are and who’s in this process?

Elliottete Friedman Sure. The reported bids are, one of them is Michael Andlauer. He is a minority share of the Montreal Canadians. He’s been involved in the American Hockey League and the Ontario Hockey League in Hamilton. He’s been the quietest, like nobody has heard from him, and in a process where the NDA has been completely disrespected, not that I care remind you, and this has been very public. He is the one guy who has been very, very quiet. He has had his eye on the Ottawa Sanders for quite some time. And, he’s in, in good standing with the league. There’s Steve Apostolopoulos. He is a billionaire in the Toronto area. He put a bid on on the Washington Commanders. I believe that, he also has had some contact with Gary Bettman about not buying theArizona Coyotes, but maybe helping him talk to some people who might, you know, depending on how this vote goes in Arizona, influence the future of the Arizona Coyotes. He’s another person who in NHL circles isn’t as well known, but he’s someone who around sports team circles has become better known recently. There are the Kimmel brothers, Jeffrey and Michael, they’re also based in Toronto.

They had a minority ownership of the Pittsburgh Penguins. They were bought out when Fenway sports owned the team. I know, their family a little bit, you know, the family name is on the pool at, Bloorview Children’s Hospital, which is a hospital that I support. They also, know the NHL and the NHL knows them very well. That’s the group that The Weeknd is part of. And there’s also, I think, the most interesting bid, Nico Sparks, who’s a producer based in Los Angeles. And he’s the one that Snoop Dogg is part of the bid. And I had heard the rumour is that in the first round of the bidding, the non-binding process, he had the highest bid at about $925 million. Now, at that point, they’re just sort of separating the groups and now you’ve gotta put that money up for real. I think he’s been upset that he feels he hasn’t been taken seriously at times. I’ve never spoken to him. I’ve spoken to people who know him and they say he’s a really interesting guy, but at this point in time, there’s been some questions about does his group have one major owner or is it a whole bunch of different people combining for percentages? And that’s not what the league is gonna want. You want big percentages if you can get them. People have told me don’t underestimate him. Don’t underestimate his will. And he’s been pushing because I’ve heard he feels that with all this talk about Ryan Reynolds, know who I know, like Snoop Dogg. So it’s pretty fascinating.

Jordan Heath Rawlings The big names like Reynolds as you mentioned, but mostly now Snoop and the Weeknd. What do we know about how involved they are, what kind of role they might have? Or are these guys just, you know, big celebrity names that can make a bid look really flashy and stylish and you know, we’ll never catch them dead sitting out in Canata?

Elliottete Friedman Well, you know, we’ll talk. We talked a lot about Reynolds. What I would also say about Reynolds is he presented a marketing plan, which I heard was like Ottawa against the world. And I heard people just loved it. First of all, he’s got a connection to the region. It’s legit. I mean, you know, when he throws himself behind a sports project, we’ve seen him with Wrexham. Like, you don’t have to question him. He’s all in. He does a good job. Snoop Dogg, he loves hockey. I remember Scott Oak interviewing Snoop Dogg before the start of a period during the 2007 Stanley Cup final between Ottowa and Anaheim. Scott went over to him. Snoop was, it was set up. He knew it was happening. He was sitting in his seats. It was a great interview. We were all laughing our heads off, and we played that clip in our intro to this show, just so you know. Well, I should credit Scott’s son. I believe it was Darcy, who’s the magician now? If I remember correctly, Scott called Darcy, before that interview and said, look, this is who I’m talking to. How do I speak to him? And Darcy was the one who gave Scott the notes, on how to ask the question. And it was, it was brilliant stuff.

So like, Snoop Dogg loves hockey. If you watched his interview on First Take on ESPN, you know, like, how could you not want that guy in the game after hearing what he had to say? And it’s legit. I don’t like, sometimes people talk and you think it’s BS, I don’t think any of that is is BS from Snoop Dogg. He loves the game. Now, the Weeknd we first mentioned his potential interest in on hockey night in Canada and our pod last fall or winter. And the connection with him is, first of all, he and the Kimmel’s, they own like an ESports gaming team. So they know each other, like there’s a history between the two of them. And also, The Weeknd has close friends, including one of his managers. Amir Esmailian grew up in Ottawa, so he has connections to the market. And the one thing I’ve also heard is that like The Weeknd is legitimately part of the financial package for the bid he’s involved in. Like one of the things people always debate is when someone lends their name to this, do they put in cash or, or do they get a piece? And like for example, when Macklemore and Marshon Lynch became minority partners in the Seattle Kraken, like I heard, you have to put in cash. And I think some relationships are very different. But most cases you’re required to put something in. I’ve heard that The Weeknd is definitely a part of this financially.

Jordan Heath Rawlings Now that we’re at the process where, the cutoff is passed and the bids are in, or at least the bidding groups that are in, are in. Who decides which bid to take? Is it the NHL and are they looking because I have another question about the Sparks bid in a minute, but are they looking for anything more than who has the most cash? Who will pony it up? Who will separate themselves from the pack? ,

Elliottete Friedman Who has the most cash is a lot of cases the winner of these things. Yes, that is what you have to default to. But there are other parts at play. First of all, can you prove the financing. Secondly, what does your ownership group look like. Thirdly, is there, are there any red flags in your history. Like I think if it’s all close, it can go to, is there one person we like better than, we don’t for any particular reason. It can be anything from a history of working with them to something that goes wrong in a meeting and you say, I don’t like this person. But it starts with money and it goes from there. Now the other thing too is there’s the family that’s selling the team, represented by Anna and Olivia Melnyck. There’s the bank, which is handling this, and there’s the league, and basically between the league and the family, I don’t think anybody can really force anyone to do something, bu they can block someone from doing something. So at the end of the day, everybody kind of has to be on the same page. Like for example, the Melnycks, in theory could say that we wanna sell to this person, and the league can say, we don’t like that person, and you can do what you want, but we’re not gonna approve it. Like, I think at the end of the day with, with this or any of the other bids, it’s gonna come down to do you have the money or not? And B, what’s your structure like in the NHL? In most structures, there’s one person who owns a lot, or there’s two people who own a lot. One of the more unusual ones is Maple League sports and entertainment, where it’s one telecom, 37 and a half. One Telecom 37 and a half, and then Larry Tanenbaum 25%. But most of them are not like that. Most of them, it’s one person with a majority share, and that’s generally the way that the leagues like it, in all sports. Like they don’t really like, like I remember one thing that happened with Vegas was after Bill Foley got the franchise. He sold, a bunch of partnerships in the team, which has worked out very well. But I remember at the beginning the league wasn’t sure they were happy about that. So they like it to be one primary person or two primary people. Like for example, the Devils, at least for now, Harris Blitzer, they’re good with that. But generally you want one person with control.

Jordan Heath Rawlings I guess my last question is just, and you kind of touched on it a little bit there, as we wait to see what eventually happens, you know, what are the next steps? And from your point of view, as somebody who’s covered a bunch of these during your time working this beat, how strange has this one been? I mean, I’m a layperson, you know, I follow the NHL for sure. It’s probably the star power doing it, but I can’t remember a recent bidding process at least that has generated these kind of headlines.

Elliottete Friedman Well, this has been unusual. You’re, you’re right about that, Jordan. Like, you know, if you look at football, they just had a pretty public sale process with the Washington commanders, but that one was not as crazy as this one. This is one of the craziest ownership sales I’ve ever seen. And as a reporter, I love it. I think it’s great that this is out in the open, right. But I’m betting that the organization and the league didn’t like it very much. You know, I don’t know if you listen to our podcast, and you’re probably more sensible if you don’t, but we had a conversation, Jeff and I, a week ago about how someone called me and said, does a NDA mean anything in sports?

Jordan Heath Rawlings Right. I remember that.

Elliottete Friedman He said to me like he couldn’t believe how much talking there was going on. So this has been very, very unusual for sports and I think in most cases, sale or sale conversations tend to stay more private.

Jordan Heath Rawlings One tiny last question. Because you just mentioned the NDA I know the NHL’s probably not thrilled about that part of it, but isn’t this great press for the league? I mean, how could they imagine like national, international media would be interested in the sale of maybe the smallest market Canadian club?

Elliottete Friedman Oh, I think they’ve gotta be ecstatic, I think. I think overall, Like I, I remember at one of the Board of Governor’s meetings, it must have been the one in December when we were asking the commissioner about Ryan Reynolds and he had that grin on his face. Like, this is awesome. And I, I think it has been very good for the league look like having Snoop Dogg on ESPN on First Take is very good for the league. The Weeknd potentially being interested is very good for the league, but I know the commissioner, he likes control and they did lose control of this process and he won’t like that. But I think overall, yes, it’s been good for the league. One of my friends actually this morning was saying to me, Jordan, he thinks it would be hilariously funny if like one of the groups would out a celebrity after they actually got the team, after all of this. He said, that would just be so hilarious. At the end of it.

Jordan Heath Rawlings And so typically NHL, you have to admit.

Elliottete Friedman Yeah. It would be like, I’ll tell you this, they wanted Reynolds in the league. They did, and someday this will all come out like it always does. And I think that was part of the frustration of the last two weeks. It’s because I think Reynolds was frustrated and I think the league was frustrated because like I said, I think the league preferred Reynolds not join a group and Reynolds was obviously very happy with what the Remington group was willing to do with them.

Jordan Heath Rawlings And when it all does come out, you gotta come back here and tell us all about it. Thank you, Elliotte.

Elliottete Friedman My pleasure, Jordan. Anytime.

Jordan Heath Rawlings Elliotte Friedman of SportsNet of Hockey Night in Canada, and of course of the 32 Thoughts podcast, which you really should listen to if you want more inside stories like those. That was The Big Story. For more from us, head to TheBigStorypodcast.ca. You know, by now you can follow us on Twitter @TheBigStoryFPN. If you want to write to us, the email address is hello@TheBigStorypodcast.ca. And if you wanna call us up, (416)-935-5935 is how you leave us a voicemail. You can find The Big Story in any podcast player you like and you can ask for it on any voice device by saying play The Big Story podcast. Thanks for listening. I’m Jordan Heath Rawlings. We’ll talk tomorrow.