35. Paul Caddick - $225m

The little-known Paul Caddick was, for a time, a star of rugby in England. For those of you who don't know what rugby is, picture an NFL game and then imagine the players without the padding. If you think that looks like it would hurt, you're right. Injury forced Caddick to retire from playing the game in 1980, but his involvement in the sport would continue.

He'd trained as a civil engineer even before he stopped playing rugby and opened his own engineering firm shortly after retiring. Fast forward thirty years, and that firm is now one of the largest in its sector in the whole of the United Kingdom. Caddick, like Dave Whelan, decided to invest the profits of his success back into the sport he loves, and purchased the Leeds Rhinos rugby team in 1997. With his financial backing, they finally ended their 32-year championship drought by winning the 2004 Super League Final.

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