The last month or so has been a bit bumpy for the New York Yankees, but Aaron Boone’s squad is beginning to turn the ship around. The Yankees are still second place in the AL East, only three games behind first-place Toronto and well within striking distance of a top-two seed come October. As such, we can anticipate an active trade deadline for GM Brian Cashman and the front office.

New York is almost always a buyer — such is life as the Yankees — but there is more pressure than usual this time around. The Yankees are looking to claw their way back to the World Series after Juan Soto’s back-breaking decision to sign in Queens. Aaron Judge is back in the driver’s seat to win MVP, but the roster around him needs work. A lot of it.

One of the primary focal points will be the bullpen. The Devin Williams trade has not paid off like expected. Luke Weaver and Tim Hill are enjoying phenomenal campaigns, but neither is much of a long-term solution. The bullpen depth is lacking, to say the least. So New York needs to add a couple arms, ideally.

One target on their radar is Pittsburgh Pirates reliever Dennis Santana.

Yankees take interest in familiar face Dennis Santana at trade deadline

New York has been in “regular contact” with the Pirates, per NY Post’s Jon Heyman. Pittsburgh evidently has several players the Yankees are interested in, including a couple former Bronx Bombers: Isiah Kiner-Falefa and yes, Dennis Santana.

Santana was on the Yankees roster just last season, in fact, but he’s enjoying a highly successful campaign in Pittsburgh. The 29-year-old has a 1.56 ERA and 0.82 WHIP with 29 strikeouts through 40.1 innings pitched. What he lacks in pure velocity and strikeout stuff, Santana makes up for with elite command. He can get batters chasing outside the zone with his slider and he almost never surrenders free bases. Few relievers in MLB operate with more poise and precision than Santana right now.

So why is he in Pittsburgh to begin with? Because the Yankees DFA’d him after he began last season with a 6.26 ERA through 23 appearances and 27.1 innings. Pittsburgh added him for cheap in free agency and Santana has been a buzzsaw ever since.

Yankees’ Dennis Santana pursuit is an admission of own failure

Did Santana just suddenly get better in Pittsburgh? Or did the Pirates put him in a better position to succeed, allowing Santana to work in more concentrated doses while handling high-leverage, late-inning situations? Pittsburgh’s track record of pitching development is fairly strong, even if not much else goes right in that organization. But this feels like a reflection of how the Yankees deployed Santana more than anything else.

Adding an elite setup arm like Santana at the deadline would profoundly benefit the Yankees. This is good business if Cashman can get a deal across the table. But there’s also no way to process a trade like this without a tinge of regret. New York sure wishes Santana was able to achieve his current status as a shutdown, high-leverage arm while he was still in a Yankees uniform. Now it will cost precious assets to get him back.