The New York Yankees suffered a heartbreaking defeat in the World Series against the Los Angeles Dodgers, and the team must quickly pivot to improving their roster for another run at the Fall Classic. The Yankees will be active in free agency, but general manager Brian Cashman must also look to the trade market to improve his team this offseason. There are several holes on the Yankees’ roster, from the bullpen to the starting rotation and the lineup. Below are four Yankees trades the franchise must consider this winter.

The Yankees must acquire a shutdown closer

One of the most important things that the Yankees must do this off-season is acquire a bonafide shutdown closer. That’s one thing that the team never truly had this season.

Yes, Clay Holmes was elite in the early going, and Luke Weaver emerged as a critical asset down the stretch and into the postseason, but there was never that one guy who truly felt automatic. And when the Yankees had a one or two-run lead going into the ninth, there was always at least a little bit of concern.

Furthermore, even if Weaver is the real deal and his dominance continues into next season, there’s no such thing as having too many shutdown options. The Yankees likely would not have blown Game 1 of the World Series if they had another option to go to after Weaver.

Luckily for the Bronx Bombers and their fans, the perfect player is available this off-season, although he won’t come cheap.

The Oakland Athletics are consistently one of the league’s cellar dwellers, and they are also a notoriously frugal organization that won’t pony up the money it takes to re-sign top talent. The Athletics also happen to feature arguably the league's best closer in superstar reliever Mason Miller.

Miller features a lethal combination of a fastball that tops out at 103 or even 104 miles an hour with plenty of movement along with a nasty portfolio of offspeed breaking pitches that cause hitters to swing wildly out of their shoes.

In many ways, Miller is like a younger and even better version of Aroldis Chapman without the wild accuracy issues and off-field baggage.

Adding Miller would give the Yankees a true shutdown closer with a proven track record. The combination of Weaver pitching the eighth and Miller coming on for the ninth would be terrifying to opponents and would make a win virtually automatic any time the Yankees have the lead after the seventh inning.

The Yankees need to add a star pitcher from a small-market team

Detroit Tigers pitcher Tarik Skubal (29) throws against Cleveland Guardians during the fourth inning at Game 5 of ALDS at Progressive Field in Cleveland, Ohio on Saturday, Oct. 12, 2024.
Junfu Han / USA TODAY NETWORK via Imagn Images

The next thing that the Yankees must be preparing to do is to add another star starting pitcher. Assuming that the team picks up the extra year to void Gerrit Cole’s option, they’ll have Cole leading their pitching staff along with the emerging Luis Gil. Beyond that, though, nothing seems to be a sure thing. Nestor Cortés Jr. is talented and fans love him for his grittiness, but he’s really a top-end number two at best.

Also, Cortes might miss next season due to Tommy John surgery. Carlos Rodon has ace-level stuff, but he’s maddeningly inconsistent. Clarke Schmidt doesn’t have quite the ceiling as Rodon nor does he have as low of a floor, but he’s also somewhat inconsistent and is really a second-level pitcher of best.

The top targets for the Yankees this off-season must be pitchers with ace-level talent who may be on the trade block if their teams feel that they can’t afford to pay what it will cost them around once they reach free agency. One player who has been heavily rumored to be available on the trade market would be Garrett Crochet from the Chicago White Sox.

Two other players who might be dealt if a godfather offer is tendered are Tarik Skubal of the Detroit Tigers and Shane McClanahan of the Tampa Bay Rays. Skubal emerged this year as one of the top five pitchers in the world, and he has a couple of years remaining on his current deal, which will make him very expensive.

McClanahan is in a very similar situation, except that the Rays have a track record of trading players before free agency and McClanahan also has a somewhat concerning injury history that could drive his price down slightly. That would probably be offset by a premium Tampa Bay would love to extract from the Yankees for trading to a divisional rival, but a deal could get done.

For both of these players, any offer would likely need to begin with Spencer Jones and Roderick Arias. Cashman’s counterparts will likely ask for Jasson Dominguez, but Cashman should be ready to counter by offering additional young players with upside in order to keep Dominguez on the big league roster.

A first base power bat from a divisional rival

The Yankees declined Anthony Rizzo’s team option, allowing him to become a free agent and sign with anyone. The Yankees may make an offer to Rizzo, but it shouldn’t be too much above the veteran minimum and Rizzo likely won’t accept.

At this point in his career, Rizzo isn’t the defensive stalwart that he once was.

Ryan Mountcastle is significantly younger and would likely provide more value on the defensive side of the coin just because of his superior athleticism. At just 27 years old, he has plenty left in the tank, and it can be argued that his athletic prime is still ahead of him. Mountcastle would be able to make the kind of plays at first that Rizzo failed to make in the postseason. He’ll be able to field balls and beat runners to the bag.

Mountcastle is also a legitimate power threat with a 30-homer season already under his belt.

The biggest downside to trading for Mountcastle is that it would require the Yankees to do business with their archrival Baltimore Orioles. It’s already tough enough to see a consequential deal signed between two AL East rivals, and the Orioles figure to be contenders for the next several seasons, which makes a deal even less likely.

That doesn’t mean it’s impossible, though. Cashman might just have to pony up more assets and tack on a higher premium than he would likely be comfortable with. That being said, it could be worth the extra assets for a potential game-changer at a position of need.

A potential offensive superstar and middle-of-the-lineup bat

Luis Robert Jr. will be one of the most sought-after players on the trade market this offseason because the White Sox have indicated that they would be willing to deal him, his performance has somewhat dampened the acquisition cost, and he still has superstar outside if he can put all the pieces together. Granted, that’s a tall ask if it’s possible, but he has always been a talented and exciting yet flawed player.

However, the Yankees have to be intrigued by his pure talent and what he could be if he can unlock his potential, which is a true five-tool player who can play shutdown defense in centerfield while hitting for average and power in the heart of the order.

Brent Rooker is a future star at just 27 years old who gets on base at a near 40% clip while hitting for power as well as average. Rooker is the type of player who a team can build around, and he would form a three-headed monster with Aaron Judge and Juan Soto if the 26-year-old Dominican superstar can be re-signed in free agency. Rooker is a right-handed hitter, but that shouldn’t stop the Yankees from pursuing him because he’s one of the game's best, in terms of hitting triple average in power.