Remember when Brian Cashman said, “We’ll go to town to improve our weakness.” It looks like the Yankees are following through with it. They are going all in for a solution by ruining the dreams of the team that broke their heart, the Blue Jays.

The Yankees suffered injuries to key pitchers like Gerrit Cole during the season, which took a heavy toll on their rotation. 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. Because when asked about his chances to return to the Mets, the $102M star responded, “50-50.” He has been open about not favoring the Yankees’ cross-town rival. “I love New York. I would love to stay in New York, but if I have to go another place, I would be happy… I like the organization. You know, if they came with the best deal for me, I’d enjoy to stay with them, but at the end of the day, I don’t know what they’re thinking.”

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.

Meanwhile, 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.

The competition seems head-to-head, though. While Díaz “loves New York,” he has also mentioned his desire to “win a ring.” And Toronto’s heat is probably still echoing around LA!

Edwin Díaz’s 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

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.

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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.