With the Ryan McMahon experiment failing, the New York Yankees are prioritizing an upgrade at third base this winter.

However, the Bronx Bombers will likely look to the trade market instead of free agency. The team does not feel comfortable pursuing Teruaki Sato due to his defense at the hot corner. At the same time, Sato is by far the best available third baseman on the open market, with a steep drop-off after him. So if the Yankees don't want Sato, free agency is not an option.

New York may not need to look too far for an intriguing trade option, though. The AL East rival Baltimore Orioles are desperate for starting pitching and outfield upgrades, to the point that they're willing to listen to trade offers for any player besides star first baseman Pete Alonso (per Andy Kostka of The Baltimore Banner).

While shortstop Gunnar Henderson would be the biggest prize should the Orioles make him available, there is another option that the Yankees should be interested in: Jordan Westburg.

How Jordan Westburg solves the Yankees' third base problem

Westburg would be a high-risk, high-reward trade target, as his biggest obstacle is staying healthy. The 27-year-old has been plagued by injuries throughout his young career, playing just 107 games in 2024 and 85 games in 2025. He also missed the entire 2026 season due to a torn UCL that needed Tommy John surgery.

But when healthy, Westburg has been an asset on both sides of the ball. He bashed 18 home runs in 2024 and 17 in 2025 and recorded an OPS of .792 and .770 in those respective seasons.

Defensively, the right-hander split time at second and third base in 2024 but looked far more comfortable at the hot corner, with a Fielding Run Value of +3, per Baseball Savant. Westburg subsequently spent most of 2025 at third, registering a +1 FRV.

Westburg's power plays well to all fields, being capable of pulling rockets to left and driving the ball the other way with authority. His opposite-field power makes Yankee Stadium's short porch an attractive target. A free swinger, Westburg doesn't walk much and has a less-than-ideal .312 career on-base percentage. However, he can improve that over time thanks to the Yankees' emphasis on developing good plate discipline.

If Westburg can avoid injury, his hitting prowess and solid glove at third would be an instant upgrade over what the Yankees currently have. His youth and club control (still under pre-arbitration) also give him plenty of room to grow.

How the Yankees can pull off a Westburg trade

While trading with a division rival would be a roadblock for the Yankees, it should not be a concern after the trade deadline. New York negotiated with the Orioles for catcher Adley Rutschman when Baltimore made him available. Rutschman ultimately went to another division rival, the Red Sox, further indicating that Baltimore has no problem dealing within the AL East.

The Red Sox's package for Rutschman was centered around starting pitching and outfield help, and those remain the Orioles' main priorities in any additional trades. The Yankees should have no problem finding a starter to include in a package for Westburg; right-handers Elmer Rodriguez and Carlos Lagrange are two highly regarded pitching prospects, while fifth starter Will Warren has multiple years of control and untapped potential that can interest Baltimore.

Finding an outfielder would be more difficult for the Yankees, as they wouldn't want to part with Spencer Jones. The need for Jones only looks to increase with Trent Grisham on his way out.

However, 23-year-old Jasson Dominguez can be used as a trade chip instead of Jones, thanks to his high ceiling that can be realized with a change of scenery. Perhaps the Yankees can also entice the Orioles with Heliot Ramos, as he'd see more playing time in Baltimore than he would in the Bronx, although it's far more likely that Baltimore would want Dominguez or Jones.

Sending promising futures to a division rival will certainly be a bitter pill for the Yankees to swallow. But the sheer amount of rotation depth and high-end outfield talent makes it more palatable in the short term, and getting a player like Westburg can fill an immediate need and provide long-term value.

Aaron Judge wants the Yankees to go all-in this winter and assemble the best roster possible. Trading for Westburg, while risky, is the kind of creative all-in move the Yankees should make.