Larry's holding a winning ticket

When considering who stands the most to gain from an expanded sports betting market in Canada, there is one name that surfaces rather easily.

Over the past 50 years, Larry Tanenbaum, chairman and minority owner of Maple Leaf Sports and Entertainment, and his close-knit network of business and political leaders has been central to Ontario’s story of pro sports teams, venues, media and legalized betting and gaming. We at The Parleh believe Tanenbaum has positioned himself and his partners to cash in from what may be the TSN Turning Point of sports betting in Canada.

Tanenbaum’s connection to gaming goes back at least 15 years to when son-in-law Jordan Gnat, then CEO of Boardwalk Gaming & Entertainment (funded by Tanenbaum’s Kilmer Capital), initiated a plan partially financed by Ontario Lottery and Gaming Corporation to convert bingo halls into gaming centres. In 2010, Paul Godfrey, who had previously aligned with Tanenbaum to try and bring the NFL to Toronto was appointed to the OLG board as chairman, along with Tanenbaum’s lawyer Dale Lastman as a board member.

Not long after that, in 2011, Tanenbaum orchestrated the biggest coup to date in Canadian sports and media when he brought both Bell and Rogers into MLSE as his partners. Together, Tanenbaum and the two telco giants control not only Canada’s entire sports broadcast industry but also the Toronto Maple Leafs, the most valuable Canadian sports franchise, as well as the NBA’s Raptors, MLS’s Toronto FC, the CFL’s Argonauts, the G-League’s 905, the AHL’s Marlies, and a pair of esports franchises.

With that kind of control over content, it’s no wonder that MLSE was DraftKing’s first Canadian sponsorship deal way back in 2015.

Tanenbaum is also likely one of the most involved and hands-on owners in all of North American professional sports, along the lines of Robert Kraft or Mark Cuban. Not only is he a member of the NHL and MLS executive committees, but he is also the NBA’s Chairman of the Board of Governors - that would technically make him commissioner Adam Silver’s boss.

Of MLSE’s properties, Tanenbaum is well positioned to exert the most influence over the CFL through Lastman’s role as chair of the board of governors combined with MLSE’s ownership of the CFL’s linchpin franchise, the Toronto Argonauts. There’s also Tanenbaum’s partner Bell Media, whose CFL broadcast rights deal for TSN and RDS has been the league’s white knight over the last decade.

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While Tanenbaum watched his teams win championships over the last few years, his son-in-law continued on his gaming apprenticeship. Gnat spent six-plus years at betting technology giant Scientific Games followed by a stint at The Stars Group (before it was acquired by Flutter) and finally Fox Bet. More recently, Gnat has launched Playmaker Media, which is backed by Toronto based venture capital fund Relay Ventures, which just also happens to be heavily invested in Score Gaming and Media.

That would be the same Score Gaming and Media behind theScore Bet mobile app that just secured access to its fifth market in the United States and is determined to own the Canadian market once single-event betting is legal.

As is the case in every dynamic sports destination, Toronto sports media pundits tend to obsess over the comings and goings of players, coaches, management and ownership. Turn the calendar back just a few years, and Toronto’s magazine for the city’s social elite painted a bleak picture around Tanenbaum’s last stand. His teams have collectively won five championships since that article was published. If the planets align - and the likes of Auston Matthews, Mitch Marner, and, of course, the Maple Leafs’ current messiah of the mesh Jack Campbell keep chugging along -  the city’s most coveted prize possession may be had after 60 years of failing and futile flailing. In what has become a common theme, betting against Tanenbaum is a losing proposition.

So how exactly might Mr. Tanenbaum profit from a legal single-event betting in the true north strong and free?

The Parleh is an objective observer, a gatherer of data, and a sharer of insights to inform and educate on all things sports betting. We are your servants of speculation and we also take great pleasure in connecting the dots that underpin what’s driving the sector.

As states south of the border continue to legalize betting, we’ve begun to see a fusion of professional sports teams and sportsbooks. In Washington, DC, fans at the Capital One Arena can place bets at the William Hill sportsbook on premise. Renderings recently surfaced of a planned sportsbook located within Wrigley Field. Therefore, it seems inevitable that we will see in-person sports betting come to Real Sports Bar & Grill. Owned by MLSE and located within cheering distance of Scotiabank Arena, pre-pandemic, Real Sports was a popular destination to watch notable sporting events and an on-premise sportsbook makes far too much sense not to happen.

It has also been speculated in several corners that Tanenbaum and MLSE are the driving force behind the CFL’s forthcoming arrangement with the XFL. Is there a play there for Redbird Capital’s private equity to bet on a combined XFL and CFL, and deliver a pro football property to satisfy football-crazy sports bettors in the NFL offseason? Redbird does have ties to Tanenbaum through his former co-owner at MLSE - current Redbird partner Nicole Musicco spent over 16 years at the Ontario Teachers Pension Plan.

In whatever way sports betting plays out in our houses of government, the sports and entertainment venues and broadcast media channels tied to MLSE will capitalize on sports betting. And why shouldn’t they? They are the most valuable sports and media assets across our great land.

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