Maple Leafs Sports & Entertainment is looking for a new chief executive officer after news broke Thursday that Tim Leiweke will be leaving on June 30, 2015 or until a successor is hired.

Leiweke, who was hired in April of 2013, said the reason for leaving is to pursue the opportunity of starting his own business. With his impending departure, fans are left to wonder how their teams Toronto Maple Leafs/Raptors/Toronto FC will fair going forward.

Let’s start with the Leafs. After being 10 minutes from advancing to the second round of the Stanley Cup playoffs in 2013, the team failed to make the post-season this past season. In the aftermath, Leiweke hired Brendan Shanahan to run the franchise as the new president.

One of Leiweke’s first moves when he came on board was to fire Bryan Colangelo and bring in Masai Ujiri as general manager. Under Ujiri’s first season, the team surprised the entire NBA by winning the Eastern Conference’s Atlantic Division, then losing a heart-wrenching seven-game series to the Brooklyn Nets in the opening round of the playoffs.

After years of failure, Leiweke made a big splash with Toronto FC, overhauling the roster by adding Michael Bradley, Jermain Defoe, Gilberto and Julio Cesar (on loan). Now, the Reds are in position to make the playoffs for the first time in franchise history.

How will all this play out moving forward?

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