It’s not easy finding the downside in the hiring of by MLSE of Tim Leiweke.
In fact, we’ll come out and say it: There is no downside; it’s a lottery ticket; scratch and win baby.
The list of candidates that can hold a candle to his resume in the world of sports and entertainment doesn’t exist.
He ran a company, Anschutz Entertainment Group, widely considered the most significant of its kind. He was on the board of the Los Angeles Lakers; had his fingers on the pulse of the Los Angeles Kings and the paid very close attention to the Los Angeles Galaxy of the MLS.
Add it all up and Leiweke had his fingers in 11 championships in his 17 years running AEG.
And he wasn't an anonymous suit. The Kings won their first Stanley Cup in 2012 and Leiweke was enough of a presence that Kings captain Dustin Brown lamented his departure from AEG last month thusly: "I knew him really well off the ice. We've been through a lot," Brown told the Los Angeles Times. "He was very adamant and very passionate about the Kings and everything that was what this organization was about. … He always had my back."
Not that anyone has forgotten, but the next championship an MLSE team wins in any sport will be the first in its 15-year history.
So it's hard not to get excited when Leiweke, after his hiring by MLSE was announced Friday, says things like:
"We need to win some trophies and hang some banners."
Or: "I think about winning the Stanley Cup in Toronto and what it would mean to the sport and the city and to the organization and I can't think of anything I want to build that is better than that."
Or: "The Raptors have 36-million fans (as the only NBA team in Canada); it's the No.1 market in the NBA I want them to act like it. I want them to be the dominant franchise in the NBA. And in order to do that we have a lot of work to do there.
Or: "That soccer team (TFC) wrote the book on how to do an expansion team in the MLS and it lost its way … but I'm excited about soccer, we have some ideas on how to bring that to the next level and reward those fans and bring back the fans that have left."
He can say those things with conviction because he's helped teams win championships in all of the leagues MLSE has failed to win in.
It's completely refreshing and a necessary change in the conversation in Toronto, where the narrative has long gone stale: On one hand you've had well-heeled and well-intended owners fail to quite grasp the nuances required to win big in big-time sports. On the other you've had capable and experienced management seemingly trying to rush the job to please the well-meaning owners who in turn want to reward the long-suffering fans.
The result has been more of the same: good intentions that miss the mark and lack a clear mission.
Under Leiweke the mission is plain. "Win championships."
Breaking that cycle will be Leiweke's signature.
Given his background pursuing an NFL team for AEG and Los Angeles, there's little doubt that landing an NFL team for Toronto will be on the agenda, somewhere.
It's the one piece missing from the sports and entertainment monolith that MLSE minority owner Larry Tanenbaum and his right-hand man Dale Lastman have been scribbling about on napkins for more than 15 years now; painstakingly assembling pieces and assets and partners in the longest of long games.
Leiweke might be just the man to spearhead such a venture and if a decade from now the MLSE empire includes a massive, state-of-the-art stadium with an NFL team to put in it, owned either by Tanenbaum in partnership with MLSE or by the Rogers family in partnership with MLSE, the news on Friday will be an obvious place to start the back-story.
But if over all those years the Leafs and the Raptors and even TFC fail to win some championships, the headlines won't have changed, and Leiweke will have failed.
And this is where it gets tricky.
As welcome as the news that Leiweke and his family are going to call Toronto home certainly is; he wears a suit, not a jersey.
Arguably there has never been a time when a charismatic executive could have less of an impact than in the NHL and the NBA today.
For all the talk about Leiweke's passion and leadership with the Kings, last we checked they won their Cup thanks to rock-solid goaltending by Jonathan Quick; an exceptional post-season run by stud defenseman Drew Doughty and depth, size and quality upfront in the form of Anze Kopitar, Brown and Jeff Carter, among others.
The Los Angeles Lakers have been winners in the NBA because they had the foresight to acquire Kobe Bryant on a draft night trade in 1997; the presence of Hollywood to lure Shaquille O'Neal as a free agent in 1996 and over the years the wherewithal to spend well over the NBA's luxury tax threshold to keep them both or add other stars as needed.
Leiweke getting hired is yet more evidence that the people who own MLSE really do want to win and their latest move demonstrates they are desperate to find someone to who can show them how to do it.
But the challenges remain the same the day before Leiweke arrived as they do now that he's shown up.
In the NHL there's a hard salary cap and big market teams don't have nearly the advantage over their weaker cousins that their bottom line suggest they should. And while the ingredients required to win a Cup haven't changed, assembling them has become an almost random-seeming exercise bolstered by hot goaltending. The Leafs are big market in every way, it's just that in the NHL the system is rigged against them taking advantage of it, and Leiweke can't change that.
In the NBA the salary cap has become much more restrictive meaning that cost of spending like the team with the potentially biggest fan base in the league has never been more expensive. Will BCE and Rogers -- owners of MLSE -- be willing to pay the kind of exorbitant luxury taxes that recent NBA champions have had to swallow? Also, with a cap on individual salaries the games' biggest stars -- who championships tend to follow -- will likely continue to congregate in warm and/or glamourous places.
Toronto, for all its strengths, is neither, meaning it either needs to bottom feed and hope to get lucky in the draft or hope that stability and consistency of approach -- think Indiana, Memphis, Utah, Detroit in the mid-2000s -- will yield results.
It's why news Friday that Leiweke would make a determined run at bringing 10-time NBA champion coach Phil Jackson to Toronto as team president -- and presumably replace Bryan Colangelo -- should be greeted with a grain of salt: Having the Raptors simply mentioned in the same breath as Jackson is flattering, but does paying a rookie executive (Jackson) $10-million a year turn DeMar DeRozan into Kobe Bryant, circa 1999?
Toronto winning an NBA title may very well take long and committed tank job. If Leiweke is willing to shoulder that burden, more power to him, but there is no need to pay anyone $10-million a year to help.
And as for soccer -- well, in a league where the commissioner seems to control which teams get the best players, maybe Leiweke's charm and influence with the league office might help TFC win a title or two, so there's that.
But in the NHL and the NBA the challenge for Leiweke is that winning doesn't necessarily correspond with a force of personality. A lack of leadership surely is detrimental, but a presence of leadership guarantees nothing.
If there is a downside to MLSE going out and signing the No.1 free agent in the sports executive market that might just be it:
When it comes to winning an NBA title or a Stanley Cup all the leadership and vision in the world don't equal a big, gifted No.1 centre for your hockey team; or a guy who can hoist an MVP award for your basketball team.
If Tim Leiweke can figure out how to get some guys like that that to Toronto, he's better than even his resume suggests.