Jay-Z, Robinson Cano and Roc Nation Sports — Will Rapper’s New Agency Fail?

Today (April 2), New York Yankees second baseman Robinson Cano left his agent Scott Boras to sign with Roc Nation Sports, a new arm of Jay-Z's fledgling management company that will represent athletes.

"Because of my love of sports, it was a natural progression to form a company where we can help top athletes in various sports the same way we have been helping artists in the music industry for years," Jay-Z said in a statement.

Sources tell ESPN that in addition to his rap career, Jay is planning to become a certified agent, dealing with baseball first, then basketball and football.

This is not the first time a rapper has gotten into the sports management business -- Master P infamously launched No Limit Sports Management in the late 90s -- but there's obviously more at stake here because, well, it's Jay-Z. And Jay-Z's not just a business man, he's a business, man.

Or is he?

Make no mistake, Jay stays winning. His list of accomplishments is longer than ours (and yours, most likely) ever will be. But in his storied career, he's taken a few Ls along the way. Will Roc Nation Sports be another? Hopefully not. Still, let's not forget Jay's biggest missteps.