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TSN Senior Correspondent

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Underscoring how difficult the search for a replacement for chief executive Tim Leiweke has become, Maple Leaf Sports & Entertainment board members are planning to hire an executive search firm to help find Leiweke's successor.

The move comes five months after Leiweke first told the sports holding company that he plans to quit and leave Toronto next summer. The MLSE board initially planned to find a replacement for Leiweke on its own. But recruiting has been difficult.

Some candidates pursued by MLSE haven't been interested in being interviewed because of the fractious relationship between MLSE co-owners Bell Media, Rogers Communications and construction magnate Larry Tanenbaum.

"I think the temptation was too great for MLSE to just try to work off the list of people they considered two years ago when they hired Tim, but circumstances have changed since then," said a person close to the MLSE board. "It's become apparent that the board is going to be an issue for any incoming CEO to manage."

Some prospective candidates simply haven't worked out. MLSE has interviewed former Madison Square Garden executive Hank Ratner, but decided that wasn't a good fit. Others interviewed for the position include NHL executive John Collins, who has helped to build the NHL's business through savvy marketing and a host of outdoor hockey games, but he also was instrumental in awarding the NHL's Canadian TV rights to Rogers.

That might complicate his hiring, since Bell Media also sought those rights. Bell is TSN's parent company.

Large companies and sports leagues often hire executive search firms to connect with prospective candidates.  The CFL, for instance, has retained a firm to find a successor to former commissioner Mark Cohon.

If MLSE does, indeed, retain an executive search firm, the move would also suggest that John Cassaday, the recently retired CEO of Corus Entertainment, might not be as much of a lock for the job as some in the sports industry have suggested in recent months.

As recently as a December, MLSE board members discussed with Leiweke whether he might consider staying on as CEO.

But Leiweke's mind is set on leaving to become an entrepreneur. The latest proof of that is his move to quit work as a full-time employee of MLSE. Since New Year, Leiweke has been acting as a consultant to the MLSE board, not the company's CEO, a move that lowers his tax exposure, according to two people close to the MLSE board.

Leiweke will leave MLSE with a mixed legacy. He has helped to rekindle the Raptors, hiring GM Masai Ujiri, convinced the company's board to invest in a $30-million practice facility for the basketball team, and negotiated a $100-million expansion of BMO Field.

But he's also ruffled feathers.  

During his first days on the job, Leiweke talked about planning a Stanley Cup parade route through downtown Toronto.

"Occasionally my energy level and my drive and my bullish attitude towards attacking problems and solving problems is hard for some people," he said during an August interview with TSN 1050. "But that's, I think, why they wanted me here. They knew and I knew that that kind of style is not a style that lasts for 10 years."