CHICAGO — The fourth word out of Alex Bregman’s mouth at his introductory news conference Thursday was “winning.” It was also the 10th, the 29th and the 38th. Over and over during his news conference, the word was used by him and it was said about him.
“I’m a winning baseball player and focused on winning,” he said.
There is nothing subtle about this guy.
Bregman’s whole deal, what separates him from other stars, is winning games, and it’s why the Cubs felt comfortable investing $175 million in a third baseman in his early 30s.
There are great players and great winners, and Bregman, who turns 32 in March, is both.
His career wRC+ is 133, his WAR is 43.1 and his TWTW is infinity. Since 2017, Bregman has made the playoffs every year, winning two World Series and losing two with the Houston Astros.
“My two most important things to me are my family and winning baseball games,” said the husband of one, father of two, and third baseman.
I suspect he gave the correct order, but I’m not positive.
“The City of Chicago loves sports and they love winning and hopefully we can win a lot for them.”
Alex Bregman has already immersed himself in Chicago sports culture. pic.twitter.com/u7gD5en23q
— Marquee Sports Network (@WatchMarquee) January 15, 2026
Bregman’s potent mix of measurable success and intangibles is why Cubs president Jed Hoyer was so publicly and privately upset when he couldn’t close a free-agent deal with him during the beginning of spring training last year. Hoyer knew his team needed Bregman. It’s why Hoyer was so happy Thursday.
“I think anyone who’s spent time around our office, around me, knows that this is a player that I’ve coveted for a long time, that our department has coveted for a long time,” Hoyer said.
Without Bregman, the Cubs had a nice season, winning 92 games (three more than Bregman’s Red Sox), finishing second in the NL Central and losing a divisional playoff series in five games to their small-market rivals, the Milwaukee Brewers. Had they beaten the Brew Crew, the Cubs had neither the starting pitching nor the hitting to compete with the Los Angeles Dodgers in the NLCS.
Since the season ended, Hoyer has rejiggered his bullpen, said goodbye to Kyle Tucker, and added Bregman in free agency and starting pitcher Edward Cabrera via trade. Do you think Shohei Ohtani and Andrew Friedman are quivering in their mansions? No. But the Cubs are a better team today than they were when the Brewers were posing with an L flag at American Family Field on Oct. 11.
There are winning teams and there are contenders, and the 2025 Cubs were the former. Hoyer disputed this characterization, but he also just signed Bregman to a five-year deal with a no-trade clause and significant deferrals.
Money talks. And this deal was loud and clear.
The Cubs are basically trading Tucker for Bregman. Nothing against Tucker, who validated Hoyer’s trade of Cam Smith for a one-year rental with an MVP-caliber first half. But he was known for being quiet and minimalist in terms of his clubhouse presence and work habits. A nice guy, a fine player. Best of luck to him in Los Angeles, where he’s cashed in on a monster four-year deal.
But Bregman is going to be a loud baseball maximalist in the Cubs clubhouse.
“I think that sometimes we can overcomplicate what we’re trying to do here,” Hoyer said. “Every night, we’re trying to win a baseball game. And I feel like every single day, I think he’s in there in the video room with the hitting coaches trying to figure out not just him, but team-wide, how are we going to win that game, and I think that’s an obsession that he has.”
PINCH-HIT 3-RUN BREGGY BOMB 💣 pic.twitter.com/vNeleVQQPM
— NESN (@NESN) July 20, 2025
“I’ve been obsessed with the game of baseball since I was a kid,” Bregman said. “I’m always trying to get better at the game, and I just want to win, and I’m excited about this opportunity here and hopefully winning a ton here.”
Hoyer said he’s heard the stories about Bregman’s intensity going back to his college days at LSU. And one of his closest friends in baseball is A.J. Hinch, who was Bregman’s manager in Houston. Hoyer didn’t enter this pursuit blindly.
“I’ve talked to AJ a lot about Alex over the years and what he brings,” Hoyer said. “Just the incredible intensity every single day in the video room, in the cage, trying to develop a plan to win that night. And so I felt like I had pretty good inside knowledge of what he brings.”
Hoyer said he spent parts of last season hashing out a plan to possibly use contract deferrals with chairman Tom Ricketts and the Cubs’ business operations department. A winning team brought in more than a few wheelbarrows of money, including five home playoff games. Once Bregman announced he was opting out of his deal with the Red Sox after a solid season in which he put up an .821 OPS in 114 games, he said it felt like it was just “seconds” until Hoyer contacted him and his agent, Scott Boras. If last year’s deal fell apart due to contractual minutiae, Bregman figured out quickly that things were different in Chicago. The Cubs were now set up to win a deal, not just finish second.
“Yeah, I did,” he said. “I feel like we had a lot of conversations over the course of the maybe three months of the offseason, numerous calls with Scott and Jed. And in our Zoom, it was pretty evident that they wanted me to be here.”
Maybe it was Hoyer panting at the screen, but the Cubs showed him the money and respect, and he wiggled out of Boston’s grasp and into Chicago.
Is the deal a risk for the Cubs? Sure.
Previous big-money contracts for veterans Jason Heyward and Dansby Swanson have certainly had mixed results, particularly in terms of offensive production. Heyward never figured it out at the plate, and Swanson, who still has four years left on a seven-year, $177 million deal, has been a slick-fielding shortstop and a bottom-of-the-order, just-above-average hitter.
Obviously, Hoyer feels pretty confident that Bregman won’t be an albatross now or in his mid-30s. This is Hoyer’s big swing for the time being.
“He makes contact at an elite level, he controls the strike zone at an elite level,” Hoyer said. “And certainly, those are skills that age well.”
After years of deserved criticism for less-than-dynamic ownership and middling budgets, Ricketts should get a rousing ovation at the team’s fan convention Thursday. With the celebration of the 10th anniversary of the 2016 World Series beginning this weekend, there’s a certain amount of symbolism in announcing the Bregman deal.
It shows that the Cubs are back to being the kind of big-market team that is obsessed with winning over everything else. This isn’t just a Lakeview real estate group with a company baseball team or a franchise with goals of winning the NL Central. (They haven’t done that since 2017.)
Let the show begin. pic.twitter.com/cxUzJ8LA04
— Chicago Cubs (@Cubs) January 14, 2026
The Cubs hope that Bregman’s intensity is infectious. He should be a great role model for young hitters like Pete Crow-Armstrong, Matt Shaw and Moises Ballesteros, and he’ll fit in quite well with veterans like Ian Happ, Swanson, Michael Busch and Nico Hoerner, the latter of whom should be extended, not traded.
After the deal was done, he went over to Jameson Taillon’s house in Arizona. Bregman has already talked or texted to pretty much the entire organization outside of Rick Fuchs, the quick-trigger scoreboard operator, and Clark the Cub. He’s excited to meet up with his new teammates at the convention, and he knows what the topic of conversation will be.
“Just talking baseball, talking about winning, talking about how we’re all looking to get better and play good baseball this year and win a lot of games together,” he said. “I feel like you can sense the excitement here, not only from the Cubs fans, but also the players are very excited as well. And that’s good.”
And it’s necessary.
It was 71 years between World Series appearances for the Cubs. These last nine have felt like a lifetime. The organization was lifted up in 2016, and the fall back to earth was jarring.
Bregman was a rookie with Houston in 2016. He faced them in early September, homering off John Lackey and hitting an RBI double against Jake Arrieta in Houston. Bregman, like everyone else, was glued to the TV watching their dramatic run through the World Series.
“What I really remember is this city and how fired up they were for that championship run,” he said. “Hopefully, we can do that again.”
With that in mind, he said he’s wearing No. 3 because he wants a third World Series ring.
To Chicago’s delight, news of the deal broke during the fourth quarter of the Bears’ playoff game against the Packers last Saturday, just before Caleb Williams led his team on its first touchdown drive of the night. Bregman — a Bears fan by virtue of growing up in New Mexico, the home of Brian Urlacher — was getting ready to watch the game in Arizona when he found out the deal was getting close.
He and his wife, Reagan, went out to dinner to celebrate and watch the game. When the news leaked out during the comeback, and his signing was now karmically tied into the Bears’ fortunes, Bregman said he thought, “This could go one of two ways. I hope they win.”
The Bears did win, of course. The Bregman effect has already begun. And yes, he’ll be at Soldier Field on Sunday.