The New York Yankees really messed up with this move two years ago, and they are still feeling the effects.
Two years ago, the New York Yankees cobbled together one of the best bullpens in baseball with a bunch of names that even the most diehard baseball fans had never heard of.
Among them was Dennis Santana, whom the Yankees signed as a free agent in December 2023 and ultimately placed on the big-league roster thanks to an impressive showing in Spring Training.
Except Santana did not last long in the Bronx.
The right-hander made all of 23 relief appearances for New York before being waived and claimed by the Pittsburgh Pirates, where he has since developed into one of the best relief arms in the sport.
To be fair, Santana posted a 6.26 ERA during his brief stint with the Yankees, but you could clearly see that there good stuff there. I remember even thinking he was potentially closer material while watching him pitch.
He certainly flashed it after landing in Pittsburgh that season, logging a 2.44 ERA while racking up 50 strikeouts over 44.1 innings. Then, last year, Santana pitched to the tune of a 2.18 ERA with a minuscule 0.867 WHIP across 70.1 frames. He also collected 16 saves. What do you know? He can close.
Pittsburgh Pirates pitcher Dennis Santana. Credit: Kevin R. Wexler-NorthJersey.com / USA TODAY NETWORK via Imagn Images.And those numbers are All-Star level stuff.
To put even more salt in the Yankees' wound, Santana has posted a 1.00 ERA through his first nine appearances of 2026.
It seems relatively safe to say that Santana is a stud, and with New York's bullpen imploding over these first couple of weeks, the Yanks could definitely use him right about now.
It's rare to see the Yankees miss that badly on a pitcher. The organization has typically been pretty sound in its evaluation of arms, especially with Matt Blake in tow. But clearly, New York whiffed on Santana.
Now, the Yanks are left with David Bednar, Camilo Doval and Fernando Cruz at the back of their rotation, and while Cruz has been solid, both Bednar and Doval have been helter skelter thus far in 2026.
Heck, they've been like that ever since the Yankees acquired them at the trade deadline last summer. New York landed Jake Bird, too, and we see how that has gone.
The bullpen is one of the Yankees' biggest weaknesses right now, and while Santana wouldn't solve it all on his own, he would definitely be a major help.
One caveat: Santana is slated to be a free agent at year's end, so if the Pirates fall out of the race by early August, perhaps New York could re-acquire him at the trade deadline.
Yankees Roundtable also offers a fan community and message board. We’d love to have you join us to talk all things Yankees. Click the “Join” button at the top of the page to join our community for free.