14. Pedro Feliciano: Two Years, $8 Million, 2011 Offseason
Pedro Feliciano's story has an exceedingly sad ending, so we won't dwell on his Yankees career or get vitriolic; after being diagnosed with a heart condition in 2013, the ex-Mets reliever passed away in 2021.
Still, this deal must be included on any list simply because of what the Yankees received for their money: nothing.
Feliciano signed with the Yankees after a successful 2010 season with the Mets, where the sidewinding left-hander posted a 3.30 ERA and led the league in games pitched with 92, his third straight year of leading in that category.
That made it exceptionally ironic when he went on to appear in a grand total of ... zero games with the Yankees in two years, diagnosed with a torn anterior capsule and rotator cuff, due in large part to the Mets riding him so hard during his time in Flushing.
Feliciano tried to come back in 2012, but never did. Fittingly, he finished his career with a 3.97 ERA in 25 games for the 2013 Mets. Some franchises have all the fun (with Pedro Feliciano specifically).