Brian Cashman faces a bullpen crisis as the trade deadline approaches. The Yankees’ bullpen has emerged as a major weak link, blowing 7 leads in the last 10 games. On Wednesday, an MLB insider handed the Yankees an ultimatum to fix the issue.

“They need to be better in the bullpen,” noted New York Post’s Joel Sherman on his podcast, Pinstripe Post. “They have got two-thirds of a season for that to happen before the postseason. They have to fix it in this third, both internally and externally, by either some of the guys getting better, calling up guys, changing jobs of some starters, reaching out of the organization, and making good trades.”

The Yankees have dropped five out of their last ten games, and they have seen some leads vanish in those games. The latest was on Friday during their 4-2 loss against the league-best Tampa Bay Rays.

With Gerrit Cole on the mound, the Yankees were leading 1-0 till the seventh inning. The ace delivered scoreless six innings, walking three and allowing two hits to the Rays hitters. But reliever Tim Hill blew the lead, while the Yankees’ offense went mostly quiet, other than a one-run triple from Jazz Chisholm Jr.

Hill came in to pitch in a one-run game in the eighth inning and recorded his worst outing of the season. He gave up four runs (three earned) on three hits. Hill was removed after 11 pitches, as the Rays took a 3-1 lead on a single and a two-run-scoring double.

Camilo Doval took the mound in the middle of the eighth inning and promptly gave up one more run, giving the Rays a lead of 4-1. The right-hander holds a 5.40 ERA and 1.10 WHIP in 23 games this year. The Yankees acquired Doval before the trade deadline last season.

During their mid-season crisis in 2025, Cashman acquired David Bednar and Doval via trade. Both relievers have underperformed, mirroring Cashman’s track record with bullpen acquisitions over the past decade.

According to the New York Post on X, Sherman observed, “There’s been a lot of bad Yankees trade for relief pitchers over, say, the last 10-15 years. This is a year they are good enough to win. They are going to have to hit it, making a trade or two, probably from outside, and still find some inside stuff.”

Against the New York Mets on May 17, the Yankees’ bullpen blew a 6-3 lead, as Bednar blew the save. Instead of closing out the Mets in the ninth inning, Bednar allowed a game-tying, three-run shot to Tyrone Taylor. Hill surrendered the final run on a ground-out single from Carlos Benge. In 23 games, Bednar holds a 1-3 record, posting a 4.70 ERA this season.

With their recent struggles and the trade deadline approaching, the Yankees should not delay in addressing the bullpen problem. As Sherman suggested, they could bring some internal changes, like using Ryan Weathers from the bullpen, when their rotation is at full strength. In 2026, Weathers posted a 3.14 ERA across 10 starts for the Yankees. Once Max Fried recovers from his elbow bone bruise, the Yankees can use Weathers from the bullpen.

Apart from trading some new relief arms, the Yankees can also call up top prospect Carlos Lagrange from Triple-A. However, Lagrange is throwing in the rotation for the Scranton/Wilkes-Barre with a 4.78 ERA across 10 starts. If the Yankees call him up, they will have to develop the 23-year-old into a relief arm.

Meanwhile, the Yankees have signed a pitcher to a minor league deal.

Peter Strzelecki to strengthen Yankees bullpen 

The New York Yankees’ bullpen is the part of their roster that needs major reinforcement. Gerrit Cole and Carlos Rodon’s returns have already strengthened the Yankees’ rotation, and the Yankees will have a surplus with Max Fried’s return. However, Ryan Weathers alone can’t anchor the bullpen if sent there.

The Yankees’ signing of Peter Strzelecki appears to be a step to fix the bullpen problems. They signed him to a minor league contract on May 23. He will head to the Yankees’ Triple-A affiliate, Scranton/Wilkes-Barre. His last MLB game was in 2024 for the Cleveland Guardians. He threw 11.2 innings in 10 games, recording a 2.31 ERA.

The Milwaukee Brewers signed him in February this season, but designated him for assignment this month before the Yankees signed him. He was out of options. This year, for the Brewers Triple-A affiliate, Strzelecki threw 19.2 innings across 16 outings, logging a 4.12 ERA.