The New York Yankees don’t have time to waste this winter. After tying the Toronto Blue Jays atop the AL East but falling short in the postseason, Brian Cashman made it clear — there will be no rebuild, no half-measures, and no waiting for prospects to figure things out.
Aaron Judge is still in his prime, Gerrit Cole will soon return from Tommy John surgery, and the Yankees have a roster that’s too talented to take a step back. The mission is obvious: build on what worked and patch the holes that didn’t. Here’s what their three biggest moves could look like.
1. Cody Bellinger gets his long-term deal
Bringing back Cody Bellinger should be the Yankees’ top priority, and there’s every indication they feel the same way. After a resurgent season in which he hit .272/.334/.480 with 29 home runs, 98 RBIs, and elite defense across the outfield, Bellinger proved to be one of the most valuable pieces on the roster.
He also played 152 games — his most since 2019 — and gave the Yankees the durability they’ve been missing from their everyday players. His left-handed bat plays perfectly at Yankee Stadium, and his versatility makes him indispensable.
Extending Bellinger in the range of six years and $170 million seems like a realistic outcome. It’s a big investment, but compared to the $300 million-plus that someone like Kyle Tucker would command, it’s great value for a 30-year-old who’s fully bought into playing in the Bronx.
2. Devin Williams receives a two-year offer with a 2028 club option
The Yankees’ bullpen will look different in 2026, but one key decision should be simple — give Devin Williams a two-year offer that includes a 2028 club option. The 30-year-old closer had a tough regular season (4.79 ERA over 29.2 innings) but showed flashes of his dominant self during the postseason, posting a 1.50 ERA in six playoff innings.
A two-year deal allows the Yankees to see if Williams can bounce back without a super long-term commitment. He still generates elite swing-and-miss numbers when healthy, and if he returns to form, they’ll have one of the best late-inning arms in baseball again.
It’s a low-risk, high-reward move that protects the bullpen and buys time to evaluate younger relievers — and Williams has the kind of upside you simply don’t walk away from after one inconsistent year.
3. Trading for Steven Kwan to fix the leadoff void
The Yankees’ lineup needs more contact hitters, and that’s where Cleveland’s Steven Kwan comes in. Trading for Kwan would give New York a true leadoff hitter — a lefty bat who doesn’t strike out and plays elite defense in left field.
Kwan hit .272/.330/.374 this past season with 11 homers, 56 RBIs, and an 8.7% strikeout rate. His on-base skills and defensive value (22 defensive runs saved, five outs above average) make him exactly the kind of player the Yankees have lacked for years.
It would likely cost them one of their top prospects, perhaps even outfielder Spencer Jones, but Kwan’s fit is too perfect to ignore. Pairing him with Judge and Bellinger gives the Yankees a balanced top three that blends patience, contact, and power — something this offense desperately needs.
Building a contender around Judge’s prime
For the Yankees, this offseason isn’t just about spending; it’s about alignment. Extending Bellinger locks down a cornerstone, a two-year deal with Williams protects their bullpen, and trading for Kwan injects the kind of consistency that wins October baseball.
It’s not about making the biggest splash — it’s about making the smartest ones. And if these moves come together, the Yankees will enter 2026 looking not just reloaded, but truly built to win.