Remember when Brian Cashman said, “We’ll go to town to improve our weakness.” It looks like the Yankees are following through with it. After a hard end to the 2025 season, the Yankees had a lot of problems they needed to solve, especially their fragile pitching department, which fell apart before the season started. And got worse as the season progressed, but now, they are going all out trying to solve this problem by ruining the dreams of the team that broke their heart, the Blue Jays.

We know the Yankees suffered injuries to major pitchers like Gerrit Cole during the season, and it took a heavy toll on the Yankees’ rotation. But even other parts of their pitching, like the closer and relief pitchers, broke down and could not step up this season. And one of them was Devin Williams. After Williams’ move failed in 2025, as reported by Fireside Yankees, “The Yankees have interest in signing Edwin Diaz this winter, per Ken Rosenthal.”

The New York Yankees and Toronto Blue Jays have shown interest in free-agent closer Edwin Díaz. Díaz posted a 1.62 ERA with 28 saves and 98 strikeouts across 66.1 innings last season. Toronto has met with its agents and could move Jeff Hoffman to the 8th inning. The Blue Jays aim to strengthen their high-leverage relief and are willing to spend significant money.

The Yankees face a pressing need for a top closer after Devin Williams struggled in critical moments last season. Edwin Díaz’s four-seam fastball consistently sits in the upper 90s, paired with an elite slider, fitting New York’s bullpen profile. A contract of four to five years, around $20 million annually, would make him the highest-paid reliever in baseball. Adding Díaz would allow Aaron Boone to manage multi-inning outings and stabilize late-game situations effectively.

If the Yankees sign Díaz, he would provide a shutdown presence in the ninth inning, increasing team confidence. Toronto remains a potential competitor, but the Yankees’ urgent bullpen requirement gives them a strategic advantage. His WHIP under 1.00 demonstrates consistent command, further justifying a high-value investment for New York. The addition of Díaz could transform late innings, addressing one of the Yankees’ biggest weaknesses last season.

The Yankees’ pursuit of Edwin Díaz shows Brian Cashman is serious about fixing bullpen disasters decisively. Toronto may flirt with Díaz, but New York’s desperation for a closer makes it the frontrunner. If Díaz signs, expect late innings to no longer feel like high-stakes guessing games for fans.

Other bullpen arms the Yankees could go after

The Yankees have made it clear they won’t settle for “just fine” in the late innings; patchwork relief and wishful thinking won’t cut it in 2026. With October dreams on the line, Brian Cashman’s office is scouring the market for arms that can actually close games instead of creating highlight reels of blown leads. The right acquisitions could transform the Bronx Bombers’ bullpen from a weak link into a full-blown weapon.

The Ryan Helsley case is clear: in 2025, he posted a 4.50 ERA over 56.0 innings, with 63 strikeouts and a 1.54 WHIP. He has shown bounce‑back potential after leading the league with 49 saves and a 2.04 ERA in 2024. For a franchise seeking late‑inning reinforcement, Helsley offers a mix of proven success and urgency to perform under pressure.

Meanwhile, the Raisel Iglesias profile brings veteran stability: in 2025, he recorded 29 saves, a 3.21 ERA, and a 1.00 WHIP across 67.1 innings. He amassed 147 saves from 2021‑2025, marking him as one of the most reliable closers of recent years. If a team restructures its bullpen with intent, Iglesias could serve as the anchor in the 9th inning while Helsley builds or transitions into a high‑leverage role.

If the Yankees land Helsley and Iglesias, late innings could finally stop feeling like a gamble. Cashman’s strategy would replace bullpen chaos with calculated firepower, demanding respect from every opposing lineup. Fans watching could trade anxiety for excitement, imagining Bronx late-game heroics instead of another blown lead.