Two years ago, the Yankees broke the bank to sign Aroldis Chapman to a five-year, $86 million contract. The deal set the record for the largest contract ever signed by a relief pitcher, one that still stands today. Remember when the Yankees used to break records in free agency?
That deal, of course, represented an uncomfortable piece of arbitrage by Brian Cashman and the Yankees. Cashman acquired Chapman as a distressed asset, with Chapman’s standing unknown after his involvement in a domestic violence incident in the fall of 2015. After picking up Chapman for pennies on the dollar and rehabilitating his value in the first half of 2016, the Yankees flipped him at the trade deadline to the Cubs for a stellar package headlined by stud prospect Gleyber Torres.