“We pursue options,” Yankees GM Brian Cashman said in early July. Now, with the trade deadline approaching, the whispers behind the closed door are getting louder. According to one MLB insider, the GM is already in talks with the Pittsburgh front office.
That .500 skid in July is a stark contrast to how well they started the season and how inconsistent they are at present. It’s not any one area but the whole roster. And they haven’t targeted just one or two players from the Pirates. Instead, there are five players on the radar.
Recently, MLB insider Jon Heyman revealed an update on his X account. “Yankees have been in regular contact with the Pirates, who have a few players who’d interest NYY: Hayes, Bednar, Santana, Keller, IKF.” Ke’Bryan Hayes is a Gold Glove infielder, while Isiah Kiner-Falefa is known for his versatility in the infield. Additionally, David Bednar, Dennis Santana, and Mitch Keller are promising starting pitchers. Each of these players brings unique skills that could enhance the Yankees’ performance.
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
The Yankees need new pitchers badly because their bullpen metrics are not looking great. Their July ERA was ranked 29th in MLB, and their WHIP was 1.43. Getting high-leverage players like Bednar and Santana would make things more stable. Bednar is a seasoned closer, and Santana’s 1.56 ERA makes the bridge even stronger. They would work together to ease the strain on their arms and turn wobbly late innings into a controlled finish. This is important for Aaron Boone as he deals with ailments and inconsistency.
With Cole, Schmidt, and Gil on the IL, the Yankees’ rotation is struggling. Adding Mitch Keller, a workhorse with a 3.48 ERA and 119 innings pitched, offers the staff a reliable mid-rotation arm. The Yankees need someone who can eat innings so that Max Fried and Carlos Rodon can stay fresh and the bullpen doesn’t get overloaded.
With Cabrera out for the season, and Anthony struggling to click, Hayes and IKF could strengthen the struggling third base and utility positions. Hayes excels at fielding third base, while IKF can play anywhere on the diamond. If this trade happens, the Yankees will have a much stronger roster.
With the trade deadline approaching, these acquisitions could strengthen the bullpen, defense, or lineup. Given their recent inconsistencies, a decision needs to be made soon.
Team-wide slumps push Yankees into emergency trade mode
July has been a pressure cooker for the Yankees, with pitching, offense, and defense all struggling. After starters were injured, skipper Aaron Boone chose a bullpen game in Atlanta on July 18, which went disastrously. In his one inning, Ian Hamilton gave up three runs, and relievers followed suit as New York lost 7-3, revealing their pitching weakness.
Image Credits: Imago
Then there was the base-running mistake that summed up the problem. In the same game, youngster Jorbit Vivas tried to tag up to third base but then slowed down and got doubled off in front of a loud YES broadcast crew, who called it “inexcusable.” That mental error eliminated the chance to rally, sending Judge out of the on-deck circle and demoralizing the offense. It wasn’t merely a one-time mistake; it highlighted how the team is falling apart at the seams.
New York’s offense has struggled, particularly due to Anthony Volpe’s performance. He posted a .125 batting average in July after a poor June, and teams have exploited weaknesses in his swing. Additionally, he has made defensive errors, including a throw that hit Judge in the head as well as costly overthrows.
Conversations with Pittsburgh are intensifying as the Yankees need improvements beyond just their bullpen. With pitching issues, costly errors, and a struggling offense, GM Cashman is urgently trying to resolve these problems before the playoff run slips away.
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