Larry Tanenbaum is the one member of the ownership group of Maple Leaf Sports and Entertainment Ltd. who is not like the others.
He has his own skin in the game, as the expression goes, as opposed to those who work for his institutional partners in the sports conglomerate, the Ontario Teachers' Pension Plan and Toronto-Dominion Bank. And he approaches the ownership of the company, which includes the NHL's Toronto Maple Leafs, the NBA's Toronto Raptors and Major League Soccer's Toronto FC, a little differently.
"Larry loves this business," said one Bay Street source close to MLSE. "For him, it's beyond money and it's always been that way."
Which means, unlike a pension fund or a bank, the prospect of cashing out isn't part of the picture, at least not right now, not when his pride and joy is scuffling along on the ice and on the court.
In an interview in 2008, the MLSE chairman said he has goals in mind - championships - and a long horizon over which he intends to pursue them.
"I will give it a 15-year time frame," he said, "and by that time I'll be 78 years old. And if I haven't achieved what I should have achieved during that time frame, then it's time to get out."
That time is not now, and after years as the chairman - the public face of MLSE, even as a minority shareholder - on teams that have fallen short in competition, it's hard to imagine a scenario in which he would be a minority partner again if the ownership were to change hands. Rogers has held preliminary talks about acquiring a controlling stake in MLSE from Teachers, though no deal is near.
"Larry has to be a party to this," said one source. "But you have to make him happy and he's not going anywhere. Larry's keeping this until he's 80 - that's what he says."
Mr. Tanenbaum was not available for an interview yesterday, but multiple Bay Street sources with knowledge of his passion for MLSE reiterated the same theme - that he might be interested in increasing his stake in the company, but not in reducing it.
"All I can tell you is he's been very consistent on that point with me … he's never indicated to me that he would ever be a seller," said one source.
Said another: "The one thing I can say clearly is he is absolutely not a seller of Maple Leafs Sports. He's always interested in more? Does that mean all? All is a lot, but I know he's a buyer not a seller.
Mr. Tanenbaum has the right of first refusal on shares owned by his partners and so has the potential to make his own play for the $2-billion sports empire. But could he come up with the estimated $1.3-billion required to take out Teacher's 66-per-cent share?
It seems like a stretch, even for someone whose net worth is estimated to be in the range of $1-billion. But sources say it's within reach.
"Larry is a lot wealthier than people think. He's wealthier than even people who think they know think he is," said one source. "And Larry will pick his own partners."
He has no shortage of friends with means. "Look who he sits courtside with," said one source, referring to Toronto's reigning power couple, fellow billionaires Heather Reisman and Gerald Schwartz. "They could be partners right there."
Another alternative would be to form a consortium of wealthy individuals to take out Teachers' stake, assuming the pension fund wants to sell.
"If Teachers wants out, Larry could get 40 very rich guys in Toronto together who would love to say they own a piece of the Leafs," the source said. The same source said it's not unrealistic that Mr. Tanenbaum, who has envisioned having all of Toronto's sports franchises under a single umbrella in partnership with a broadcaster, could cut a deal with Rogers that would bring baseball's Toronto Blue Jays into a new-look MLSE.
"That's as likely as Rogers buying MLSE," he said. "All deals go through Tanenbaum."