Owner: Maple Leaf Sports & Entertainment

Wealth: Sports ownership

The MLS&E company owns the Raptors, Toronto Maple Leafs, as well as the Air Canada Centre. The company was founded in 1927 as a way for owner Conn Smythe to protect his hockey team's assets. Ironically, the largest shareholder in the company today (which has a valuation of $1.6B), is the Ontario Teachers' Pension Plan. That's right, retired teachers collectively own the Raptors. You see, Vince Carter was just appeasing the retired owners of the club with his loafing!

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