Yankees Among Favorites to Poach Red Sox’s $120 Million 2-Time World Series Champ
The New York Yankees are among the betting favorites to poach Boston Red Sox star Alex Bregman.
The New York Yankees have a long history with the Boston Red Sox, but Vegas has the Bronx Bombers potentially poaching one of the rival’s star players in MLB free agency. New York has seemingly been linked to every major MLB free agent, but it is for good reason given the club’s usual willingness to spend.
Alex Bregman’s future with the Red Sox is in doubt after just one season in Boston. Could the Yankees be among the teams pushing to land Bregman?
The Yankees are third in the odds to sign Bregman if the star bolts Boston, per BetOnline. New York sits at +400 just behind the Philadelphia Phillies (+250) as well as Chicago Cubs (+300) in the betting odds.
If you are feeling like Bregman just went through this last offseason, this would be correct. We are less than one year removed from Bregman signing a three-year, $120 million contract with Boston in February. Bregman is best known for being a 2-time World Series champion during his previous nine seasons with the Houston Astros.
Bregman opted out of the deal this offseason to once again test the free agent waters. Could the Yankees be a fit for the rival infielder?
Let’s explore the latest Yankees rumors.
The Yankees Rumors Linking Red Sox 3B Alex Bregman to New York Have Quieted
Beyond the betting odds, rumors appear to have cooled on the Yankees’ potential interest in Bregman in recent weeks. Back in September, ESPN’s Jeff Passan linked the Yankees to the Red Sox third baseman.
“Bregman has taken over the Red Sox’s clubhouse and become their unquestioned leader: a baseball rat whose wisdom is exceeded by his willingness to help his teammates find the best versions of themselves,” Passan wrote in a September 4, article titled, “Early MLB free agency intel: Tucker, Imai, Schwarber, more.” “It’s rare to find a player who has such a wide base of knowledge and the ability to teach it, too.
“… Complicating matters for the Red Sox, though, are the teams in need of better production at third that might be willing to spend for what Bregman provides. The Phillies. The Yankees. The Tigers. And it will take more than three years this time even though he’ll be going into his age-32 season. After one of the more lucrative pillow contracts ever, Bregman is bound to get the five-year-plus deal at an average annual value of $35 million-plus that eluded him last winter.”
How Will Trent Grisham’s Return Impact the Yankees in MLB Free Agency?
The Yankees received a bit of a surprise when Trent Grisham accepted the team’s qualifying offer. It is unclear how Grisham’s return will impact the Yankees’ efforts to re-sign Cody Bellinger or land another big fish in free agency.
“The Yankees likely extended Grisham the qualifying offer unsure whether he would accept it,” The Athletic’s Brendan Kuty detailed in a November 18, article titled, “Trent Grisham accepts Yankees’ qualifying offer, will return in 2026: What it means.” “As the team briefly pondered selling at this year’s trade deadline, it received inquiries on the availability of Grisham, another league source told The Athletic. So Cashman surely knew which teams might have been targeting Grisham again this winter
“… The Yankees are expected to continue pursuing Cody Bellinger, who mostly played left field for them last season but could take over in center field next year.”
Pursuing Bregman would likely be an expensive move for the Yankees and third base does not appear to be the club’s biggest priority. Spotrac projects Bregman’s market value to be a 4-year, $110 million contract.
NFL Report Delivers Major Broncos News; Denver Could Lose Rising Coach
Webb is Denver’s offensive pass game coordinator and quarterbacks coach, working closely with head coach Sean Payton and second-year quarterback
My annual look at the NFL’s rising young coaches is here, featuring potential candidates for head jobs this year, plus dozens more names their colleagues say to remember for years to come:
NFL Names Davis Webb a Top Young Candidate in 2026 Hiring Cycle
Pelissero’s annual “young coaches to know” piece focuses on assistants under 45 with no previous NFL head-coaching experience who could realistically land interviews this cycle. Webb fits the template almost perfectly.
A quick snapshot of his rise:
- Playing background: Webb was a 2017 third-round pick by the New York Giants and spent parts of six seasons with the Giants, Jets and Bills as a backup quarterback and trusted locker-room presence.
- Fast-track into coaching: He joined Payton’s first Broncos staff in 2023 as quarterbacks coach and was promoted to offensive pass game coordinator/QB coach before the 2025 season, giving him a larger role in game-planning and pass concepts.
- Preseason audition: Payton even turned play-calling over to Webb in a preseason game against the Arizona Cardinals, when Denver’s backups scored 24 points in the first half — a small but telling audition for a bigger future role.
Pelissero notes that those who know Webb believe it’s a matter of when, not if he becomes an NFL head coach. With the Broncos winning and Webb embedded in the development of a potential franchise quarterback, his name becomes even more attractive to owners searching for the next long-term leader.
What Davis Webb’s Head-Coach Buzz Means for Broncos and Bo Nix
For the Broncos, Webb’s rise is both a compliment and a looming challenge.
On the positive side, it validates the staff that Payton and the front office have assembled. Denver sits at 9-2, in first place in the AFC West, and has ripped off an extended winning streak behind a balanced offense and a resurgent defense.
Webb has become a key voice for Bo Nix, who is in his second NFL season and first full year as the unquestioned starter. In meeting rooms and on the sideline, Webb is the bridge between Payton’s system and the on-field execution, helping Nix handle protections, adjustments and late-game situations. Nix has already delivered multiple clutch drives during the streak, including a game-winning march against the
If teams start requesting head-coach interviews with Webb in January, Denver faces a few real-world consequences:
- Continuity for Nix: Losing his day-to-day position coach would mean another relationship to rebuild at a critical stage of his development, even with Payton and offensive coordinator Joe Lombardi still in place.
- Staff shuffle: The Broncos do have experienced options on staff, including Lombardi and assistant head coach/run game coordinator Zach Strief, but any change at QB coach/passing-game level would ripple through weekly prep.
- Perception of the program: From an organizational perspective, having assistants poached for bigger jobs is usually a sign you’re doing things right — but it also means replacing key voices almost every offseason.
For now, Webb remains locked in on Denver’s playoff push. But the moment the regular season ends, his name is likely to surface on interview lists, and the Broncos may have to prepare for the possibility that their rising offensive mind could be calling plays — and running a locker room — somewhere else in 2026.
