The Chicago Cubs Alex Bregman signing came out of nowhere. According to Jon Heyman of the New York Post, the team swooped in to grab the former Boston Red Sox star. The timing was comedic, as it was in the middle of the Chicago Bears Vs Green Bay Packers pivotal playoff matchup on NFL Wildcard Weekend.

This signing comes as a surprise because there was a good chance that Bregman was going to re-sign with the Boston Red Sox, especially after how highly they talked of him. The Red Sox talked ad nauseam about his leadership abilities. Most importantly, he was stout on the field, as he hit .273 with a .821 OPS in 114 games.

The full contract details are 5 years and $135 million, coming in at $35 million annually. It’s nice to see the Cubs make a big-time move like this, as they are a big-market team after all.

How Does Bregman Fit With The Cubs?

Chicago Cubs Alex Bregman Contract, Boston Red Sox
Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images

Bregman will almost certainly man third base for the Cubs. Nico Hoerner will be at 2nd base, Michael Busch will be at first base, and Dansby Swanson will be at shortstop. Chicago now has a exceptonially potent lineup that they can pencil Bregman into, which includes the aforementioned players, as well as Seiya Suzuki, Pete Crow-Armstrong, and Ian Happ. Moisés Ballesteros is also an interesting bat and will most likely get Designated Hitter opportunities.

This is a perfect bat to add either at the top or middle of the order. Bregman brings postseason experience, and also gives the Cubs an additional leader. A consistent bat that rarely strikes out, hits for average, and is still a good defender is someone that every team would take. Bregman is also elite at chase percentage, whiff percentage, squared-up percentage, and he also takes his walks.

The elephant in the room here is the fact that the previous third baseman, Matt Shaw, is now out of a starting position. Hoerner’s been floated in trade rumors; he only has one year remaining, but they really should hold onto him. Shaw would be coming off the bench in a super-utility role at this given moment, coming off a 93 Weighted Runs Created+ rookie season in his 126 games.

Are There Any Concerns About Bregman?

Alex Bregman, Boston Red Sox, Chicago, Cubs
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images

Bregman is about to enter his age-32 season and will be paid until he’s 37 years old, so there’s a chance that his play dwindles down yearly. That’s all a guessing game at the end of the day, though, but as we know, Father Time is undefeated.

Outside of that, Bregman also struggled in the second half of last season after a quadriceps injury in May. In the first half, he hit .298 with a 152 wRC+ and a .927 OPS. In the second half, Bregman hit .250 with a 101 wRC+ and a .727 OPS. This is just something to monitor with him; there’s no reason to panic, which is evident since they just gave him $175 million.

Bregman is also extremely slow, coming in at the 17th percentile in sprint speed (26 feet per second) and he only has a combined 7 stolen bases in the last 3 seasons.

The deal also involves no opt-outs and a no-trade clause, so Chicago is hoping that they see more of that first-half Bregman.

The End Of My Cubs Alex Bregman Rant

Alex Bregman, Boston Red Sox, Chicago Cubs
Oct 1, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) hits a single during the eighth inning against the New York Yankees during game two of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images

This was an intriguing signing by the Cubs, as they put some pressure on their National League Central foes, like the Milwaukee Brewers, with this acquisition.

It doesn’t seem as if Chicago will be bringing back Kyle Tucker, so they signed the cheaper alternative, who can also fill a position that wasn’t locked down at 3rd base.

There were some rumblings about Bo Bichette, but it seems like he wants too much, and they would potentially have to move Hoerner if they got him, so that’s a no-go.

It’s a ton of money at the end of the day for Bregman, but it’s nice to see the Cubs make a blockbuster-type signing for a change. They clearly, unequivocally believe in him; they just made their team even more of a contender, and now they hope to reap the benefits of this signing.

What a good time to be a Chicago fan, acquiring Bregman after trading for Edward Cabrera. Then on Saturday, Caleb Williams leads the Bears to a comeback win in his playoff debut after a stellar fourth-quarter performance against the Packers, who they absolutely despise.