Does the Yankees GM Really Believe New York is Set, or is He Planning a Daring Deal?

New York Yankees general manager Brian Cashman spent the day fielding questions from the media. He emphasized that the current roster is not the same team that was humbled by the Toronto Blue Jays in the ALCS. After an offseason focused on reeling in their big target, Cody Bellinger, Cashman knows fans aren’t impressed with simply running it back. Now, rumors are swirling that the Yankees are working on an under-the-radar move that could change the conversation and reinvigorate hope in the Bronx.

With the Yankees’ offense lacking true firepower despite respectable numbers on paper, pitching has become their default target for improvement this season. Brian Cashman and the front office know that if the lineup can’t consistently overpower opponents, the team’s best chance for contention lies in run prevention, especially through a dominant bullpen. It’s an area where Cashman has a proven track record, and this year’s moves reflect a clear commitment to fortifying the relief corps. This direction was made clear through two recent acquisitions for young arms.

The trade for Colorado Rockies reliever Angel Chivilli perfectly illustrates this strategy. Chivilli, just 22 years old, is a high-upside arm with a fastball that routinely sits 96–98 mph and can touch triple digits. According to MLB Pipeline and scouting reports, his fastball has late life up in the zone, making it a true swing-and-miss weapon. He pairs that heat with a sharp, mid-80s slider that has flashed plus potential, and a developing changeup that he’s shown more confidence in over the past season. Some scouts have also noted the emergence of a cutter, giving him a legitimate four-pitch mix, rare for a reliever his age. 

MLB evaluators describe Chivilli as a raw but electric talent whose command is still a work in progress. However, he possesses the kind of stuff that could thrive under the Yankees’ pitching development system. The organization’s pitching coach, Matt Blake, views him as a project with huge upside. The Yankee pitching whisperer believes that with some mechanical tweaks and refinement, Chivilli could become a late-inning weapon for years to come.

The Yankees’ pursuit of Ryan Weathers, expected to be used as a long-relief swingman, further cements their bullpen-first approach. By targeting power arms with multiple secondary pitches, New York is building a pitching staff designed to shorten games and cover for offensive inconsistency. In a season where run prevention may decide their fate, adding arms like Chivilli gives the Yankees a shot at turning their biggest weakness into a strength. This is just the kind of move where Cashman thrives. The other thing he does well is the trade that no one sees coming.

Brian Cashman has built a reputation for pulling off at least one surprise a year, and the Yankees’ rumored pursuit of Tarik Skubal fits that mold. Skubal, a two-time Cy Young winner, is a flourishing ace with front-line stuff and team control in 2026, is the kind of pitcher who could instantly transform the Yankees’ rotation. Detroit’s sky-high asking price, reportedly including Cam Schlittler, Ben Rice, and top prospect George Lombard Jr., reflects not just Skubal’s value but also the Tigers’ awareness of the Yankees’ urgency and deep prospect pool. For Detroit, demanding three premium young players isn’t just about talent; it’s about leveraging New York’s desperation for an ace and their well-stocked farm system.

This leaves the Yankees with a franchise-defining question. Do they believe Cam Schlittler, who flashed electric stuff in the Wild Card Series, is a future rotation cornerstone, or are they willing to trade that potential for proven present value? Is Ben Rice’s emergence as a young power bat, and Lombard’s projection as the next great Yankees shortstop, worth sacrificing for a legitimate shot at a title right now? Cashman will have to weigh the allure of immediate contention against the risk of mortgaging the team’s future, a calculus that could shape the Yankees’ identity for years to come. Skubal brings the Yankees into the World Series title conversation. It's been quite a while since they had that conversation.