Saturday night was a great night for Chicago sports fans. While they were watching Caleb Williams and the Bears pull out an incredible second-half comeback victory over the hated Green Bay Packers in the NFL playoffs, word broke that the Cubs had agreed with third baseman Alex Bregman on a five-year, $175 million contract, multiple sources told MLB.com.
The three-time All-Star and two-time World Series winner joins a team that’s eager to get back to the top of the NL Central and perhaps even back to the World Series, a decade after their title in 2016.
Here are five immediate takeaways from the deal:
Bregman was smart to get that opt-out clause
It turns out that Bregman and his camp insisting on an opt-out clause after the first year of the contract he signed with the Red Sox last offseason was an extremely savvy decision. Remember, Bregman was coming off a down year in 2024, one in which he hit 26 homers but had a .315 OBP, by far the lowest of his career. This was a player who was second in AL MVP Award voting in 2019 but no longer resembled that guy.
Despite some early injury woes in 2025, Bregman looked much more like that guy this past season, posting his highest batting average (.273) and slugging percentage (.462) since that 2019 campaign. Thus he was able to cash in and find a long-term home.
Don’t be afraid to bet on yourselves, players: It very much paid off for Bregman.
Is it finally time for the Brewers’ doubters to be right?
A whole of bunch of baseball pundits and observers -- and I’ll step right to front of the line here -- have been made to look rather silly picking against the Brewers for the last half-decade; the Brew Crew has won three straight NL Central titles and four of the last five. But I don’t see, in the wake of this deal, how you can make a case for the Cubs not to be the favorites in the division in 2026.
Putting Bregman at third and in the middle of that lineup -- along with adding Edward Cabrera in the rotation and, don’t forget, a whole bunch of bullpen arms -- puts a further spotlight on how quiet the Brewers’ offseason has been. They haven’t added anything, they’ve traded away Isaac Collins and they’re still rumored to have Freddy Peralta on the market. The Brewers found all sorts of magic the last few years, particularly in 2025, to stay on top. But they can’t keep dancing between the raindrops forever, can they?
The Cardinals’ path to trading Brendan Donovan is now clear
There has been a certain amount of consternation among Cardinals fans that both Donovan and Nolan Arenado are still on the team. Sonny Gray and Willson Contreras were both traded to Boston before the calendar flipped to the new year, but has the clearing out and rebuilding project now stalled?
But really, team president Chaim Bloom was waiting for precisely this -- for Bregman to sign. Now that the Diamondbacks have taken Ketel Marte off the market and Bo Bichette is (presumably) the next to sign, Donovan is the clear and obvious next-best option for anyone looking to add infield offense (and defense). The Mariners still make the most sense, but Bloom now should have many options from which to extract the highest reward.
Another upside: The next most appealing third baseman/infielder might be Arenado, who will not bring back much in return, one suspects, but will allow the team to clear his spot for Nolan Gorman to have one last chance to make it in St. Louis. The Cubs may have just done their rivals a favor: The Cardinals’ offseason can now resume in earnest.
The Red Sox need to do something! But what?
When the Red Sox traded away Rafael Devers last June, the move was praised by many people, including me, for being a way to clear out some future payroll that they could spend more judiciously, but still aggressively, to complement their cadre of young players. Red Sox fans now have to be wondering when exactly that money is going to get spent.
There aren’t that many guys left on the market who make sense for the Red Sox: They don’t need any more lefty outfielders, which is an issue because two of the best players left (Kyle Tucker and Cody Bellinger) are exactly that. Marte is no longer a trade option. So if the Sox don’t get Bichette and the Phillies sure look like they’re flooring it to make sure they don’t -- they’re going to end up empty-handed, free-agent wise.
Considering how active the rest of the division has been this offseason -- well, other than the Yankees, anyway -- that is asking for trouble. There are ways to add players other than trading with the Cardinals, you know.
Cubs fans finally got what they’ve been waiting for
As mentioned above, it has been 10 years since the Cubs won the World Series, still one of the biggest baseball things that has happened this century. (The Cubs won the World Series! It still feels weird to say that out loud!) But since then, from the perspective of their fans, the Cubs have been a little bit of a bummer. They’ve never made it back to the Fall Classic -- despite having a ton of young players who, at the time, made you think they might be starting a dynasty -- and in the years afterward, they slowly dismantled that team.
They have bounced back since then but still finished second to the Brewers in the division in each of the past three seasons -- including in the past two since taking Milwaukee’s manager. Yet the Cubs also haven’t really exerted their financial might in the post-2016 era, signing Dansby Swanson to a big free-agent deal three years ago but otherwise mostly staying out of that game.
The signing of Bregman seems to show – finally -- that the Cubs are treating themselves as the true power in the NL Central that their fans (and many others) felt they should have been all along. The Cubs have the strength to be the behemoth in the NL Central, particularly with the Cardinals rebuilding. Now it appears they are.