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In the nine years under manager Aaron Boone, the New York Yankees have failed to win the World Series. Boone’s tenure without a title is the longest in franchise history. He leads a talented roster filled with superstars, yet the Yankees have repeatedly come up short in the postseason. After losing to the Los Angeles Dodgers in the 2024 World Series 4-1, New York has failed to make it past the AL Division Series (ALDS). The last two Octobers have ended with defeats to division rivals, as the Toronto Blue Jays and Tampa Bay Rays have knocked them out in back-to-back falls.
Once the Yankees likely confirm the returns of Boone and GM Brian Cashman for 2027, the focus needs to shift towards doing whatever it takes to win a title in 2027. New York has a number of holes across the roster. Second and third base, along with center field and catcher, need to be addressed. So does the bullpen, and likely designated hitter. A fourth outfielder who can routinely pitch in might be needed as well. Safe to say that Cashman has his work cut out for him this winter.
There are several avenues which Cashman can explore to improve the roster. After the team’s ALDS loss to the Rays, a number of players spoke to the press, including captain Aaron Judge. Despite dealing with injuries most of the season, Judge was “not satisfied” with how the season ended. At 34 years old, his window to lead the Yankees to a title is closing, and fast. Cashman needs to do whatever is possible to juice up a squad that’s come close to October glory quite a few times. His first move? A call to San Diego Padres GM A.J. Preller to see how much it would cost to deal for top closer Mason Miller.
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Mason Miller could be long-term answer at closer for Yankees
The Yankees have a storied history of strong closers. In addition to Mariano Rivera, universally considered to be the best closer of all time, the Yanks have employed a number of relievers who navigate the final frame with success. For the last year and a half, David Bednar has been Boone’s go-to choice at closer. Since his acquisition from the Pittsburgh Pirates ahead of the 2025 trade deadline, Bednar has essentially locked down the ninth inning in the Bronx, with a few hiccups along the way.
However, Bednar is slated to hit the free agent market this winter. Furthermore, the Yankees could lose fellow veteran relievers Paul Blackburn, Michael Fulmer, John Schreiber, and Tim Hill, plus swingman Ryan Yarbrough, in free agency. Cashman will need to do some serious retooling of the bullpen, regardless of whether Boone returns or not.
Sending a big package to the Padres for Miller, who has become the best closer in baseball, would likely be worth it. While Cashman likely wouldn’t part with George Lombard Jr. or Spencer Jones, sending the Padres prospects like starters Elmer Rodriguez or Carlos Lagrange, along with possibly an outfielder like Jasson Dominguez and another piece or two, could swing a deal for the Yankees. Using another young, major league-ready starter such as Will Warren or Ryan Weathers could help as well. In any case, Cashman needs to lock down the ninth. What better way than to trade for Miller this winter?
Matt Chapman would solidify the hot corner at Yankee Stadium
Since Alex Rodriguez’s retirement, the Yankees have not had a star third baseman in their lineup. The latest primary starter, Ryan McMahon, came over at the 2025 trade deadline, like Bednar. However, that trade didn’t work out quite as well as New York would have hoped. While McMahon has maintained his solid defense at the hot corner, his bat has regressed. At 31 years old, McMahon might be starting to regress from his prime.
While trading for Chapman would also add a 30+ third baseman, the veteran has maintained his strong two-way play. Furthermore, the Giants are reportedly looking to shed salary while they try to figure out which path forward they want to take. Although Chapman has become a relied-upon veteran leader in San Francisco, the Yankees could use someone of his skill set in the lineup. Sending McMahon back out West would likely help balance out the money.
Cashman could also part with a couple of quality prospects, much like he did when he dealt for outfielder Heliot Ramos at the 2026 trade deadline. Can the veteran GM once again trade for the Bombers’ next star third baseman, much like he did for Rodriguez?
Aaron Boone could use these moves to help Yankees capture elusive title
Adding Chapman and Miller to the roster would certainly cost the Yankees some solid capital. Preller paid a high price to bring Miller to San Diego, sending the team’s top prospect at the time, Leo de Vries, plus a few others, to the Athletics. Chapman recently signed a long-term extension with the Giants and could look to finish his career on the West Coast. While San Francisco had a disappointing 2026 campaign, Chapman still showed that he’s one of the best third basemen in baseball.
Let’s say Cashman sends Warren, Dominguez, Rodriguez, and righty Rory Fox, currently in Double-A, to San Diego for Miller. Shortly after, the Yankee GM agrees to send fellow Double-A arms Ben Hess and Bryce Cunningham, plus the rising infielder Core Jackson, to San Francisco for Chapman. While the price for both players is high, so is the price to compete for a World Series title.
Adding players like this to the roster would also show if Boone is truly ready to win a title. The longtime Yankee manager is entering the last year of his current deal next spring. If he cannot win the franchise’s 28th championship in his tenth year at the helm, will Boone ever get it done? If not, then Cashman should have seen all he needs to in order to make a potential change in the home dugout at Yankee Stadium.
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