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Sidney Crosby and Alex Ovechkin

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Ovechkin Ted Leonsis

Photograph By AP Photo/Nick Wass

"I'm a risk-taker. And if you're going to make a long-term investment, who else would you do it with?" And with that, Caps owner Ted Leonsis signed Ovechkin to a 13-year, $124 million deal in 2008, the first $100M deal in NHL history.