While the World Series hasn’t even begun, the debates about whom the Yankees will pursue in free agency are already beginning to fester.
The outfield is the no. 1 priority for the Yankees entering this winter, as it was last winter, but the debate is about who Brian Cashman should sign to a big deal this winter.
On one side you have Cody Bellinger, the defensive wizard who brings versatility and speed who has shown he can play at a high-level in New York, it’s easy to envision his return to the Bronx.
There is one reason why he could leave; and that’s the option to pursue the best player on the market in Kyle Tucker, who would give the Yankees a superior chance of winning the World Series.
Despite some of the advantages Bellinger has over Tucker and the familiarity he has in New York, the Yankees have already showed their hand a year ago, and the team must act on it this winter.
READ MORE: Yankees will have a new infield free agent target this winter
Why Kyle Tucker is a Clearly Better Fit For the Yankees

When the Yankees lost Juan Soto, the organization had to pick up the pieces of a shattered pursuit that certainly created a sense of panic about where they’d replace his offensive production.
New York knew Max Fried would be part of this plan an acted swiftly, making an aggressive offer to secure a pitcher who will finish top five in Cy Young voting this year.
The next logical pivot was Cody Bellinger, whom the Cubs let known to the baseball world that they would look to trade in a salary dump.
What changed the Yankees plans briefly was a potential pursuit of Kyle Tucker, whom the Astros made available for trade, even having talks with New York about a deal.
Sources tell ESM that Astros’ Majority Owner Jim Crane had directed his front office to take a deal with the Cubs over the Yankees if the packages were similar since he didn’t want to send over a star to a hated AL rival.
Once New York got the hint that it would not get a fair deal with the Astros, their offer which included Ben Rice and Luis Gil would be pulled off the table, and the Cubs would end up with the slugging outfielder.

Kyle Tucker recorded 4.5 WAR with a 136 wRC+ in 136 games with the Cubs, dealing with a wrist injury that limited his offensive capabilities down the stretch.
While Cody Bellinger posted a 4.9 WAR in 2025, that occurred over 152 games, meaning that if you measure it on a per 150-game basis, Tucker has a 5.0 WAR and Bellinger a 4.8 WAR.
The gaps in WAR are within the margins of error for the statistic, but even in Bellinger’s second-best season as a big-leaguer, he wasn’t able to clearly surpass the production of a down year for Kyle Tucker.
Furthermore, what Cody Bellinger did in New York shouldn’t be viewed as a reason to retain him, it should be used as a reason to desperately want to import Kyle Tucker onto the roster.

Both Bellinger and Tucker have similar spray charts, with tons of pulled flyballs in the air that allow them to drive the ball out of the yard, and that is significantly hampered by Wrigley Field’s conditions.
The wind tends to blow baseballs back inside the field of play instead of allowing them to fly out of the yard, and right field in the North Side is way further from home than right field at Yankee Stadium.
Tucker had a marginally higher Pull AIR% than Bellinger, making him an even better fit for a ballpark where left-handed pulled flyballs are rewarded handsomely.
Among qualified hitters, Tucker also has the fourth-best BB/K rate (0.95), as he’s one of just three hitters with a top-10 K-BB% and a SLG% above .500 over that stretch.
The other two? Juan Soto and Jose Ramirez. Future Hall of Famers.
With more Baserunning Runs and stolen bases this past season and over the last three years, Kyle Tucker is also producing more value with his legs, but can the Yankees make this fit work defensively?

I could shut this argument down by pointing out that the Yankees didn’t care a ton about defensive fit when they were looking to sign Juan Soto to a 16-year deal, which would have put Aaron Judge in either CF or Juan Soto in LF.
They also didn’t care enough about defensive fit when they aimed to trade numerous young players for Kyle Tucker last winter, so any conversation centered around how important this is to the Yankees is hogwash in my opinion.
Remember, the Yankees could have never entered the Kyle Tucker sweepstakes last winter, which would have cleared the path for the Cubs to acquire him and make landing Cody Bellinger easier.
Brian Cashman, likely with the approval of Hal Steinbrenner, instead went hard after Tucker, and nothing’s changed in the last year for them to feel that differently.
2026 needs to be about building the best team in baseball; not just a team that’s one of the best in the American League.
The Yankees have never “deserved” to win the World Series. It was never an upset when they were knocked out. They have never assembled the kind of roster with Aaron Judge that was the best in baseball entering the postseason.

Why are the Dodgers two-time World Series Champions since 2017 with five NL Pennants?
They’re almost always the best team in baseball with the best roster. The playoffs are a crapshoot, which is why they don’t win it every year, but if you’re number one for long enough you’ll win a title.
Just because the 2019 Washington Nationals or the 2021 Atlanta Braves won it all doesn’t mean that’s the norm. The Yankees need to build the way the Dodgers do and that means signing Kyle Tucker.
It means assembling as many superstars as possible together, and that’s something they’ve failed to do with Aaron Judge in pinstripes.
They’ve had teams capable of winning it all, but never a team better than the other 29 teams, and until that changes they won’t win a World Series with the two-time MVP.
Hal Steinbrenner and Brian Cashman both know who the better player is; now it’s time to sign him and form baseball’s best offensive duo.
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