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14. Aroldis Chapman, 2016: Five Years, $86 Million
The Yankees pulled off their favorite gambit when they traded for Aroldis Chapman at a discount following the 2015 season (as he dealt with a pending domestic violence suspension), traded him at the 2016 deadline to the Cubs and secured Gleyber Torres, then re-signed him to a mega-deal in the offseason.
Wow! What a lose-lose!
Chapman had an option to depart after 2019, but somehow, the Yankees further extended this contract and kept him around for an additional three seasons and $48 million. Cool.