Alex Bregman Re-Ups with Red Sox: What It Means for the Cubs and the Market That Missed

The Alex Bregman sweepstakes are officially over-and the Boston Red Sox have come out on top once again. The star third baseman is staying in Beantown, agreeing to a three-year, $120 million deal that carries a hefty $40 million average annual value. But there’s a twist: $20 million of each year is deferred, which means Boston is spreading out the financial hit while still locking in one of the most consistent infield bats in the game.

For the Chicago Cubs, who were very much in the mix, this marks another near-miss in their pursuit of a high-impact bat. They reportedly offered Bregman the same total value-$120 million-but over four years, which would’ve paid him $30 million annually. That $10 million difference in AAV, along with the Red Sox’s willingness to structure the deal with deferrals and opt-outs, likely tipped the scales in Boston’s favor.

Let’s break down what this means for both Bregman and the teams that chased him.

Red Sox Make Their Move

Boston’s commitment to Bregman wasn’t just financial-it was strategic. They were willing to get creative to keep him in the fold.

The deal includes opt-outs after each of the first two seasons, giving Bregman flexibility and leverage moving forward. It’s a short-term pact with elite AAV, and it keeps the Red Sox competitive while they continue to develop their young core.

Bregman is coming off a solid 2025 campaign, where he slashed .273/.360/.462 with 18 home runs and a 125 wRC+ in 114 games. He looked like his old self before a quad injury sidelined him for seven weeks.

Pre-injury, he was raking-.299/.385/.553. Post-injury?

A noticeable dip to .250/.338/.386. Still, the overall body of work was strong enough to warrant big money, and Boston clearly believes he’s worth the bet.

Cubs Swing and Miss Again

Chicago’s pursuit of Bregman dates back to last offseason, when they also came up short. Back then, they reportedly offered a four-year, $120 million deal-essentially the same offer they made this time around. But once again, it wasn’t enough to get Bregman to Wrigleyville.

What’s interesting here is the Cubs’ approach. They’ve made it clear they’re not in the business of using deferred money in contracts, which may have been a sticking point.

Meanwhile, the Red Sox leaned on deferrals to make the numbers work, just as they did in their previous deal with Bregman. That kind of flexibility can make all the difference in a tight race for a marquee free agent.

It’s also worth noting that the Cubs have publicly downplayed the idea of adding a major bat this offseason. Most of their offseason chatter has centered around pitching-both in the rotation and the bullpen.

Names like Dylan Cease, Framber Valdez, and Michael King have been floated in connection to Chicago. But Bregman was one of the few position players they were seriously linked to, and now he’s off the board.

Third Base Still a Need in Chicago

Even with the emergence of Matt Shaw in the second half of 2025, the Cubs finished in the bottom five in MLB in offensive production from third base. That’s a tough pill to swallow for a team looking to take the next step. Shaw showed promise, but banking on a young player to carry the load at a premium position is a gamble-especially for a team with postseason aspirations.

Financially, the Cubs have room to maneuver. With Dansby Swanson as the only position player locked into guaranteed money beyond 2026, there’s flexibility to make a splash-either now or at the trade deadline. But with Bregman off the market, the pool of elite bats just got shallower.

Tigers, Astros Also Come Up Short

This wasn’t a two-horse race. The Detroit Tigers and Houston Astros were also in the mix late in the process.

Detroit reportedly made the biggest offer-six years, $171 million. Houston wasn’t far behind with a six-year, $156 million bid.

Both teams were willing to go long-term, but Bregman chose the shorter deal with Boston’s structure and familiarity.

It’s a reminder that sometimes, it’s not just about the total dollars. Fit, flexibility, and contract structure can be just as important-especially for a player like Bregman, who’s looking to maximize both his earnings and his control over the next phase of his career.

What’s Next for the Cubs?

Now that Bregman is off the board, the Cubs’ front office will have to pivot. Whether that means circling back to the trade market or looking at other free agent bats remains to be seen. But the need at third base hasn’t gone away, and neither has the pressure to add more firepower to a lineup that lacked consistency last season.

Pitching may still be the top priority, but Chicago can’t afford to ignore the offensive side of the equation. If they want to contend in a loaded National League, they’ll need more than just arms-they’ll need impact bats. And with Bregman now locked in with Boston, the search continues.

Final Word

Alex Bregman’s decision to re-sign with the Red Sox is a win for Boston and a missed opportunity for the Cubs. It underscores the importance of contract creativity and timing in today’s free agent market.

For Chicago, the focus now shifts to finding the next best fit-whether through free agency or trade. The hot corner remains a question mark, and the Cubs still have work to do.