The New York Yankees have been in “regular contact” with the Pittsburgh Pirates as the trade deadline approaches. The players the Yankees are interested in are David Bednar, Ke’Bryan Hayes, Mitch Keller, Isiah Kiner-Falefa, and Dennis Santana. So says baseball insider Jon Heyman of the New York Post.
Heyman: Yankees Interested in Several Pirates Players
Hard-thinking fans and pundits joke that the Pirates are merely a farm team for the Yankees. However, the reality is that the Pirates have done as well with former Yankees as the Yankees have done with former Pirates. While the Yankees fleeced Pittsburgh in deals for Jameson Taillon and Clay Holmes, the Pirates also benefited from one-sided deals for A.J. Burnett and Francisco Cervelli. On the free agent front, the Yankees signed Gerrit Cole, who neither the Pirates nor the Houston Astros could afford, while Pittsburgh outbid New York for the services of Russell Martin. The Yankees fixed the issues that plagued Holmes, as the Pirates did with waiver claim Santana.
Yet, if indeed all five of the aforementioned players are headed to New York, the joke will become a reality. Pirates insider Noah Hiles recently gave all five players a greater-than-50 percent probability of being traded by the deadline.
Yankees have been in regular contact with the Pirates, who have a few players who’d interest NYY: Hayes, Bednar, Santana, Keller, IKF
— Jon Heyman (@JonHeyman) July 20, 2025
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Yankees Looking for a Third Baseman
With the Yankees releasing DJ LeMahieu, Jazz Chisholm Jr. has moved to second base, leaving third base for Oswald Peraza. The Yankees would love to upgrade third base. Entering Sunday’s action, Peraza is hitting a woeful .147/.210/.240, 3 HR, 13 RBI, 26 OPS+, and 26 wRC+. That’s where Hayes or Kiner-Falefa, a former Yankee, would come in.
Not that the disappointing Hayes would be much of an upgrade with the bat. He’s hitting .237/.284/.293, 2 HR, 33 RBI, 62 OPS+, and 60 wRC+. However, he’d be a significant upgrade defensively. He won a Gold Glove Award in 2023 and should have won one in 2022, when he led all major league third basemen with 3.1 dWAR. This season, Hayes has been worth six Fielding Runs Above Average (FRAA) and 13 Defensive Runs Saved (DRS). Peraza, with four FRAA and four DRS, hasn’t been terrible there. The Yankees might figure that in their strong lineup, a defensive upgrade may be enough, and they might even unlock whatever hitting potential is still hiding inside Hayes.
Hayes, the subject of many trade rumors, wants to finish his career in Pittsburgh, while Kiner-Falefa wouldn’t mind rejoining his former team. “IKF” has been one of the more outspoken Pirates, including recently lamenting that the team isn’t constructed for PNC Park. Unlike Hayes, Kiner-Falefa would represent an offensive upgrade. He’s hitting .279/.321/.346, 1 HR, 24 RBI, 86 OPS+, and 86 wRC+. He’s been the Pirates’ regular shortstop, but the versatile Hawaiian native will man third base with ease.
Yankees Searching for Pitching, Too
The Yankees were recently linked to Keller, who’s in the second year of a $77 million extension with the Pirates. Cole, New York’s ace, has been out all season due to Tommy John surgery. Now, Clarke Schmidt has learned that he, too, will need the surgery. The Yankees are in desperate need of a fifth starter, a role for which Keller is overqualified. He has a deceptive 3-10 record to go with a 3.48 ERA, 3.33 FIP, 1.143 WHIP, and 123 ERA+. The former All-Star is also in the midst of a 13-game streak where he’s gone at least six innings.
In addition to the usual deals involving expiring contracts, rumor has it that the Pirates would deal players like Keller and Hayes, who are under contract for a while, to free up money to obtain a hitter, either at the trade deadline or in the 2026 free agent market. On the other hand, the Pirates don’t have to deal Keller, either. They extended him with the thought that he could be a veteran rotation anchor in the future, and he still can be. The Pirates are listening on Keller, as they are with virtually the entire roster. But they’d probably have to be bowled over with the return.
Every contender could use another reliever or two, and the Yankees are no exception. The two-time All-Star Bednar is 2-5 with a 2.53 ERA, 13 saves, a 2.03 FIP, 1.125 WHIP, and 170 ERA+. Santana is 3-2 with a 1.56 ERA, five saves, a 2.49 FIP, 0.818 WHIP, and 275 ERA+.
The Return
This writer doesn’t do mock trades, as they generally strike me as foolish, and I can look like a fool without their help. For whatever it’s worth, the Baseball Trade Values website determined that an equal trade value for Bednar and Hayes would be outfielder Spencer Jones, the Yankees’ No. 2 prospect, and right-handed pitcher Cam Schlittler, No. 6, for example.
Indeed, Pittsburgh pundits and social media denizens are obsessed with the idea of the Pirates giving up several players to the Yankees to obtain Jones. Thus, we’ll give Jones a little space before we end here. He’s a 24-year-old left-handed hitting outfielder who the Yankees drafted in the first round in the 2022 Amateur Draft out of that baseball factory known as Vanderbilt University. He was promoted to Triple-A Scranton/Wilkes Barre in late June. There, he’s putting up Ted Williams-type numbers, hitting .397/.459/.841, 8 HR, and 18 RBI in just 15 games. He’s also stolen six bases. MLB Pipeline says he’s scheduled to arrive in the major leagues this season. Will that arrival take place in Pittsburgh or New York?
Main Photo Credit: Denis Poroy-USA TODAY Sports at Petco Park
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