Cubs Land Alex Bregman on Five-Year Deal

It was a big night in Chicago. On Saturday, about an hour before Caleb Williams and the Bears defeated the Packers in the Wild Card round, erasing an 18-point deficit with a fourth-quarter comeback so furious that it earned the rare non-baseball wheeee from Sarah Langs, the Cubs elicited a different kind of dopamine rush. As Jon Heyman of The New York Post first reported, Alex Bregman has agreed to a five-year, $175 million contract to play in Wrigley Field. A year after Bregman signed a high-value, prove-it pact with the Red Sox, he’s finally gotten the long-term deal he sought, while the Cubs got a premier player to replace free agent Kyle Tucker. The deal contains no opt-outs and a full no trade clause. It’s the third-largest in franchise history, though on Sunday morning, Ken Rosenthal of The Athletic reported that it contains $70 million in deferred money, dropping the average annual value to just over $30 million. Bregman should remain in Wrigley through his age-36 season. It is a huge move, and the likely pièce de résistance for one of the most aggressive offseasons in recent memory for the Cubs.

Just in case you need a refresher on his résumé, Bregman ranked second on our Top 50 Free Agents list this winter, and for good reason. He’s a two-time World Series champion and three-time All-Star who owns a Gold Glove, a Silver Slugger, an All-Star Game MVP, and two top-five AL MVP finishes. Since his first full season in 2017, he’s accrued 41.8 WAR, eighth most among all position players. Aside from a partial rookie year and the truncated 2020 campaign, he’s finished below 3.0 WAR just once, in an injury-shortened 2021 season. (Any career recap also has to include at least some mention of Bregman’s role in Houston’s sign-stealing scheme in 2017 and 2018. Bregman would express regret about the scandal, but his initial deflections – “the commissioner made his report, the Astros made their decision, no further comment on it” – rankled fans, and his apologies fell flat with many outside of Houston.)

Bregman is no longer the MVP candidate he was in 2018 and 2019, when he ran a combined 162 wRC+ and put up 16.2 WAR, but he’s been extraordinarily consistent ever since. Not only has he averaged a 124 wRC+ over the past six seasons, he’s kept within 13 points of that mark every single year and he’s combined that offensive excellence with great defense at third. He earned MVP votes as recently as 2023, and he was on pace to pick up some more in 2025 until a quad strain and a late-August slump changed the trajectory of his season; he still managed a .273/.360/.462 line with 18 home runs, a 125 wRC+, and 3.5 WAR in 114 games.

This is a happy ending to a long, twisty story for both Bregman and his agent, Scott Boras. Bregman ranked third on last offseason’s Top 50 Free Agents list. After nine years with the Astros (including a five-year, $100 million extension in 2019), the then 30-year-old Bregman wanted a long-term contract. Despite interest from several teams, he didn’t find the deal he was looking for, though he did find plenty of dollars. Hampered by a qualifying offer, Bregman signed with Boston during spring training for three years and $120 million, with an opt out after each season (and some deferred money). According to reports, the Tigers had offered six years and $171.5 million with an opt-out after the 2026 season, while the Cubs offered four years and $120 million with opt-outs in both 2026 and 2027. Bregman bet on himself with the shorter, high-AAV deal, and he’s now cashing in. When you combine the two contracts, he ended up getting $215 million over six years, which is, according to sources, lots of money. Bregman is just the latest Boras client to successfully execute the trampoline two-step, joining Pete Alonso, Blake Snell, and Matt Chapman. Cody Bellinger is sure to feel heartened.

For the Red Sox, on the other hand, it’s looking more and more like it’s Bo Bichette or bust. Even after landing Willson Contreras, without Bregman or Rafael Devers, our depth charts have them ranked 15th or worse at every infield position (including catcher), and 20th or worse at all but first base.

As for the Cubs, they’re really doing the damn thing. At 92-70, the team had the sixth-best record in baseball in 2025, and their Pythagorean win-loss record indicated that they deserved to be even better. They made the playoffs for the first time since 2020, and they’ve certainly got enough talent around the diamond to merit going all-in. They completely overhauled their bullpen this winter, and they’ve now made a major roster improvement for the second time in four days, the first being their trade for right-hander Edward Cabrera.

With Nico Hoerner, Ian Happ, and Seiya Suzuki all due to enter free agency after the 2026 season, Bregman provides some much needed stability to Chicago’s position player group. He will slot in next to shortstop Dansby Swanson, the first overall pick in the 2015 draft (and the reason Bregman wears no. 2 on his uniform). Even though he’ll turn 32 in March, the Cubs are getting one of the best third baseman in the game right now. Over the past four seasons, Bregman has put up a combined 17.5 WAR, which ranks 18th among position players. In that timeframe, he owns three of the top 20 seasons at the position. The only other player who can say the same is José Ramírez. (Bregman’s injury shortened 2025 season also comes in at 28th.)

Bregman represents an upgrade over Matt Shaw, who will presumably shift into a utility role or find himself on the trading block. Chicago’s 0.0 WAR at third base in 2025 ranked 27th and made it their worst spot on the diamond, though that wasn’t really the fault of Shaw, who put up 1.2 WAR at third (and 1.5 overall); he was just canceled out by the negative value accrued by all five of the other players to spend time at the position. His remaining team control could make him an appealing trade target, though rumors abound that Shaw could shift to second and Hoerner could end up traded. Hoerner is due $12 million in 2026, the last year of his contract. Coming off a career-best 4.8-win season, his value has never been higher.

How the Cubs resolve their infield logjam – and which other positions they choose to bolster – will be interesting to watch. Even with Cabrera and the eventual return of Justin Steele, our depth charts have the Cubs’ starting pitching projected for just 11.2 WAR, which ranks just 19th even though it would be an improvement of nearly a full win over the 10.3 mark they put up in 2025. If they’re really going for it, the obvious next step would be to add an impact starter. Meanwhile, right field was and remains the biggest hole on the roster, but it seems unlikely that the Cubs will hand out another huge deal to fill it with the likes of Bellinger or Tucker. At North Side Baseball, Matthew Trueblood wrote that after landing Cabrera earlier in the week, ownership gave president of baseball operations Jed Hoyer permission to cross into luxury tax territory. Signing Bregman puts them right on the threshold, though it’s still possible that they’ll duck under it, especially if they trade an infielder.

If you’re a Cubs fan and you want to stop reading here, feel free to do just that. The rest of the article will be devoted to the possible downsides of the deal, and you are absolutely entitled take a couple days to enjoy watching your team make a serious bid at World Series contention without worrying about park effects and what might happen in 2030.

OK, you’ve been warned. Any long-term deal represents a risk, and Bregman will be 36 at the end of this one. He’s likely got some wear on his tires; since his debut in 2016, his 1,225 games played is tied for 23rd most in baseball, and he ranks 15th in defensive innings played. He’s also coming off an injury-shortened season where he fell off pretty hard in the second half. Then there’s his offensive profile.

Bregman has never possessed top-shelf bat speed or wowed with his exit velocities. He’s never once hit a ball 110 mph, a feat achieved by 308 different major leaguers in the 2025 season alone. Instead, he’s succeeded through a combination of elite plate discipline, elite contact skills, and a preternatural ability to pull the ball in the air in order to maximize his damage. The good news is that plate discipline tends to age well, but another way to describe Bregman’s lift-and-pull tendencies would be to say that his swing is already optimized. He’s already got something resembling the aging slugger swing that Joshua Rodrigues described so aptly last week over at Baseball Prospectus. He’s not starting out with much margin for error, so things could get ugly when his bat speed or his contact skills start to go. And Bregman is already slow and a below-average baserunner. He already has a weak arm. When the first-step quickness goes, the defense could crater pretty quickly too.

The more immediate concern is that Wrigley Field is not particularly conducive to Bregman’s offensive approach. Bregman has spent his entire career in Houston and Boston, playing in parks pretty much designed for someone with his exact swing. The shallow Crawford Boxes and the even shallower Green Monster made him look like a god. Over the course of the Statcast era, 174 players have hit at least 100 home runs. Bregman’s average home run distance of 384 feet ranks 173rd. We’re about to find out for the first time in his 10-year career what it looks like when, friendly or not, the confines aren’t tailor-made for his swing.

According to Statcast’s park factors, Wrigley Field ranks right in the middle of the pack in terms of home runs for right-handed hitters and dead last for doubles. More importantly for Bregman, the left field corner has a deep cutout; Cubs fans remember well the 85 wRC+ and .084 ISO that lifter-puller Isaac Paredes ran during his short stint with the team at the end of the 2024 season. Paredes hit just one ball out at Wrigley, to go with several more that looked like trouble for a moment before landing harmlessly in the left fielder’s glove.

So the downside is there and it’s scary. Even taking the deferrals into account, Bregman will tie up a significant proportion of Chicago’s payroll through the beginning of the next decade. Still, this is probably the wrong time for doomsaying. Over the course of his career, Bregman actually has a few more home runs on the road than at home. Should he figure out how to succeed in Wrigley, should he age gracefully, he’s got a chance of ending up in Cooperstown. It would be at least a little bit foolish to count out a player who possesses elite skills and has a succeeded at the highest level for as long as Bregman has. It’s encouraging for the Cubs to be on the rise, and it’s even more encouraging to see them acting like it.