19. Johnny Damon, 2005/Chase Headley, 2015: Four Years, $52 Million
Before "Aaron Hicks is the Left Fielder," there was "Bubba Crosby is Our Center Fielder."
That's just about the time when Brian Cashman pulled off the biggest heel turn in the history of the Yankees-Red Sox rivalry, heisting Damon after Boston's failed follow-up to the 2004 title in October 2005.
Damon went on to match seemingly impossible expectations for agitation in the Bronx after shaving his trademark "Idiot" beard, never making an All-Star team with the Bombers, but piling up two of the three best offensive seasons of his career and swiping two bases on a single play to help punch the Yankees' ticket to their 27th World Championship. Worth it. Better than Bubba.
As for Headley? Eh. The Yankees don't really make midseason trades they don't intend to extend (sorry, Andrew Benintendi), and Headley was perfectly average for three seasons/in San Diego for Year 4 of this deal.
Mostly forgettable, except when he flopped on the base paths in the 2017 ALCS against Houston.