Toronto Maple Leafs’ president Brendan Shanahan didn’t win the number one pick in the draft lottery in April – a selection the Edmonton Oilers will convert into generational talent Connor McDavid. But on Wednesday he landed what is undoubtedly the top off-ice prize entering the June draft, as the Leafs announced the signing of former Detroit Red Wings head coach Mike Babcock to an eight-year contract worth a reported $50 million.

The deal instantly makes Babcock, who stewarded Detroit to a Stanley Cup championship in 2008, the highest paid coach in the league. He also won two Presidents Trophies with the Red Wings after the team captured the most regular-season points in the 2005-2006 and 2007-2008 seasons.

Babcock, perhaps the most sought after bench boss since Mike Keenan left the New York Rangers after winning the Cup in 1994, was in play after his contract with Detroit expired when the Tampa Bay Lightning eliminated the team from the playoffs. The Buffalo Sabres, who will pick second overall in the draft and are expected to select Boston University pivot Jack Eichel, were thought to be strong contenders for Babcock’s services.

Ultimately, however, it appears Shanahan, himself a former Red Wing, was able to convince Babcock to move north of the border. It could not have been an easy sell. The Leafs finished the current campaign with an Eastern Conference record of 30-44-8, missing the playoffs for the eighth time in the past nine years.

Head coach Randy Carlyle was fired midway through the season, while general manager Dave Nonis was let go after the campaign. The Leafs have yet to name a new GM.

Shanahan has indicated that he’s ready to make major changes to the current roster and start a full-on rebuild, something his predecessor Brian Burke was unwilling to do. That puts the fate of numerous key players into question. Team captain Dion Phaneuf, a favorite source of criticism for frustrated fans at the Air Canada Centre, may well be on the block. The same may go for leading scorer Phil Kessel.

The only real untouchable on the Leafs roster may be Morgan Rielly, the team’s fifth overall selection in the 2012 draft. The Leafs own the fourth overall selection in June, and are thought to be targeting Mitch Marner, a center with the London Knights of the Ontario Hockey League, or center Dylan Strome of the Erie Otters.