How Former Yankee Pitchers Became the Trade Deadline's Biggest Losers

Heaney, who struggled mightily during a short 2021 stint in the Bronx, is a one-year deal. The left-hander owns a 4.79 ERA, 1.27 WHIP, 89 ERA+ and 20 home runs allowed in 107 innings this season. Once viewed as a back-end starter who might bring back a mid-tier prospect, Heaney's rough July likely cooled interest. Still, several teams in need of rotation depth reportedly checked in, but the Pirates didn't bite.

Then there's Santana, maybe the most surprising non-move of all. The reliever is having a breakout year with a 1.39 ERA, 0.838 WHIP, 36 strikeouts and six saves in 45 1/3 innings. Santana is also on an expiring deal and despite a seller's market for relief pitching, his value may never be higher. Yet, the Pirates held him, too.

The irony? They dealt Bednar, a former Yankees farmhand now under control through 2026. Bednar goes to the Bronx for a package of three prospects: Rafael Flores, Edgleen Perez and Brian Sanchez. Bednar brings a 2.37 ERA and 17 saves to a bullpen in need of stability. The Pirates moved their most controllable asset while sitting on rentals they will likely lose for nothing this winter.

It ads up to frustrating deadline for Pirates fans and a quiet loss for Heaney and Santana, who now finish the year on a non-contender after missing their best shot at joining a contender.