Maple Leaf Sports & Entertainment's efforts to find a replacement for chief executive Tim Leiweke have stalled in recent weeks, with some board members musing that the company should try to convince Leiweke to stay on board.
The board has spent months interviewing possible replacements for Leiweke and has been collectively surprised that some qualified candidates haven't been interested in even interviewing for the job.
MLSE is jointly owned by Bell Media, TSN's parent company, and telecom rival Rogers Communications. The perception that those companies are often at odds has made some sports executives contacted by MLSE wary.
Leiweke said in August that he plans to leave MLSE by June 2015. He has since confirmed to Bloomberg News that he has talked with Live Nation Entertainment chairman Irving Azoff about starting a joint venture that could include assets that belong to Madison Square Garden Co.
Leiweke joined MLSE in 2013 after working for 13 years for the Anschutz Entertainment Group, which owns the Los Angeles Lakers and Kings. After a rough start, when he drew criticism for a plan to remove photos of Leafs legends from the hallways of the Air Canada Centre, Leiweke won praise for his hiring of Raptors GM Masai Ujiri, and for navigating local politics to get a new $30-million practice facility built for the Raptors.
John Cassaday, chief executive of Corus Entertainment in Toronto, is widely considered a front-runner for the job. But even he has his detractors on the board. Cassaday is 60, according to Forbes.com, and some MLSE board members, a source told TSN, would prefer a younger CEO.
One person familiar with the matter told TSN that the board has realized in recent months the talent it is poised to lose when Leiweke leaves.
Several board members had discussions with Leiweke about staying on as recently as December, but that option has been abandoned, the person said.
Leiweke and MLSE part-owner Larry Tanenbaum have a fractious relationship and unless Tanenbaum sells his minority stake in Canada's highest profile company - a development that probably won't happen - Leiweke is unlikely to change his mind about leaving.
Leiweke has spent recent weeks addressing issues with TFC. Star player Jermaine Defoe won't return to the team next season and Leiweke has been trying to get MLSE the best return for him, and plotting a plan to replace him.
The story of who will replace Leiweke has percolated in sports business circles for months.
Several Toronto-based sports business executives said perhaps the best candidate to replace Leiweke would be his own brother.
Tod Leiweke, Tim's younger brother, is the chief executive of a sports holding company that owns the Tampa Bay Lightning and its arena. He previously was the CEO of the NFL's Seattle Seahawks.
"Tod's so well respected in the industry, but I really don't see it happening," said one Toronto-based sports industry executive. "How does that conversation go when Tod calls Tim and asks, 'what do you think of the board? Should I interview for the job?'"