The Yankees’ winter could start with a familiar problem and a potentially unfamiliar kind of fight.
After barely getting through 2026 with their bullpen intact, New York is staring at another offseason where relief depth has to be addressed. Tim Hill faded badly enough to end up off the postseason roster, and Brent Headrick’s heavy workload eventually caught up with him. The unit survived, but only just, and the Yankees now have to rebuild it with two important pieces headed for free agency.
David Bednar sits atop the market as the top-ranked closer available, which all but guarantees interest from across the league. Paul Blackburn is also free to leave after reviving his career out of the bullpen and giving Brian Cashman’s patchwork relief corps a real boost in 2026.
Losing either arm would hurt. Losing both would leave a hole the Yankees can’t afford to ignore.
That’s where Jim Bowden comes in with a more optimistic read for the Bronx. In his ranking of the top 40 free agents for The Athletic, Bowden also mapped out ideal landing spots and contract ideas for each player. For both Bednar and Blackburn, he points to the Yankees as the destination.
Bowden’s prediction is that New York will go to work to keep Bednar, and he projects a three-year, $55 million deal. He bases that range on past contracts for elite closers such as Edwin Diaz, Tanner Scott, and Robert Suarez.
Viewed alongside Devin Williams’ three-year, $51 million deal with the Mets last offseason, Bowden’s number looks like a price the Yankees could live with. He also suggests the qualifying offer would help suppress Bednar’s market.
Blackburn is another story, but Bowden still sees the Yankees staying aggressive. His projection for the right-hander is two years and $22 million, a contract similar to the one the Mets handed Luke Weaver last winter.
It’s not without risk, especially with Blackburn carrying only one year of elite production, but Bowden clearly believes New York will pay to keep the momentum going. The expectation is that Matt Blake and the staff unlocked something real.
Even if those two deals happen, the Yankees still wouldn’t be finished. They’d simply be back where they started, with the bullpen stabilized but not fully built out. More help would still be needed, ideally another arm or two with velocity and strikeout stuff, whether that comes through free agency or a trade.
Bowden’s biggest wild-card prediction goes far beyond the bullpen. He sees a straight-up Yankees-Red Sox battle for Teruaki Sato, the Hanshin Tigers slugger who will be posted this offseason after the club agreed to honor his wishes.
That would fly in the face of recent reporting from Joel Sherman of the New York Post, who said the Yankees would look to move Ryan McMahon this winter but would not pursue Sato because of defensive concerns at third base. Bowden isn’t buying that limitation. He believes Sato can handle the hot corner, which opens the door to the kind of old-school bidding war that used to define this rivalry.
Sato brings huge left-handed power, but the whiff concerns are real. The profile has drawn comparisons to Munetaka Murakami, whose market took a hit before his two-year, $34 million deal with the Chicago White Sox. Murakami’s 35-homer season changed the conversation again, though, and Bowden seems to think Sato could benefit from the same logic: if the power plays, teams will live with the strikeouts.
In Bowden’s view, that means a massive payday is in play. He projects five years and $180 million for the 27-year-old.
Whether the Yankees would actually go that far to beat Boston is another matter, but the need at third base makes the idea at least plausible. If McMahon is on the move, the bar for his replacement may not be perfection.
It just has to be better than what was already there.
In Other News...
Yankees Could Finally Have A Real Answer At Third Base
Several big-market clubs are expected to spend the offseason looking for help at third base, and the Yankees are right in that mix after years of trying to settle the position. The search has been ongoing enough that it has become one of the more obvious needs on the roster, and it is not hard to see why a proven upgrade would draw attention from a team that expects that corner to produce more consistently.
One name that could complicate the market is Teruaki Sato, whose Triple Crown-winning season has put him on the radar of clubs chasing an immediate answer. If he reaches free agency, the Yankees are likely to be among the teams watching closely, especially with the Phillies and Red Sox also eyeing the same type of fix, which could quickly turn a thin third-base pool into one of the winters more competitive bidding zones. [Read more 🡒]
Yankees Have Two AL East Roster Holes They Can't Ignore
The Yankees are heading into the offseason with a familiar kind of urgency, the sort that comes after an October exit forces a hard look at a roster that was close but not complete. Following their ALDS elimination, they are expected to be active in free agency, and the front office has more than one area to sort through before spring training arrives. A batch of relievers are set to hit the market, but the needs go beyond the bullpen and into places that can shape a daily lineup.
Backup catcher, third base and center field all loom as spots that need attention, and the Yankees figure to have options if they want to patch those holes with outside help. Isiah Kiner-Falefa and Cedric Mullins are among the names being tied to possible upgrades, which gives the club a sense of the kind of roster flexibility it may seek. The bigger question is how aggressive they want to be in fixing multiple issues at once, because this winter feels like one where standing still would be the easiest way to fall a step behind. [Read more 🡒]
Yankees Fans May Need To Start Watching Kyle West Closely
Kyle Wests first full season in the Yankees system gave a glimpse of his power, but his Arizona Fall League run has made the 13th-round pick a lot harder to ignore. After a .226 season in High-A with 20 home runs and 75 RBIs, the 2025 draft selection has carried that pop into the fall, where hes hitting .282 through 13 games with three homers.
The biggest attention grabber so far has been the longest home run in the 2026 AFL, a blast measured at 462 feet. For a player still trying to climb the organizational ladder, that kind of raw power is the sort of development the Yankees will want to keep tracking closely as he builds on an encouraging showing. [Read more 🡒]