Why Alex Bregman left ‘great experience’ with Red Sox for new chapter with Cubs | Chris Cotillo

CHICAGO — When Saturday began, as members of the Red Sox roster gathered at Fenway Park for the team’s annual “Fenway Fest” event, the leader of last year’s team was at home in Arizona mulling a decision. Thousands of miles away from the place he called home in 2025, Alex Bregman was coming to terms with the reality that he was likely leaving Boston after just one season.

The Cubs, who landed Bregman on a five-year, $175 million contract that includes heavy deferrals and an all-important full no-trade clause, did not swoop in at the last minute to poach him away from Boston. Chicago, after losing out to the Red Sox in the Bregman sweepstakes a year ago, began expressing strong interest in him almost immediately after he opted out of his contract in November. By the weekend, the bidding had come to a head. The Red Sox were involved to the end, offering Bregman a five-year, $165 million arrangement with heavy deferrals that stretched out decades; they refused to includ e a no-trade clause. As the Packers and Bears battled at Soldier Field, Bregman made his call.

“The process works where you define where the club is at. They let you know where it’s at,” explained Bregman’s agent, Scott Boras, when asked if the Red Sox had a chance to match. “We let the other team know where they’re at. In fairness, that’s how Alex wanted me to handle it, a “Where are you at?” and ”Where are you at?“ (conversation). Then, he made the decision.

“We got an advance (an improved proposal) from Jed (Hoyer) and the Cubs that really showed that this could get done,” Boras added. “When you’re working through the economics of net present values and financials and different equations of how you value those net present values, once you get through the science of all that, you start to get to a real platform of valuation.

“A lot of it was really that I gave Alex and (wife) Reagan a, ‘Hey, this is what one team is offering and what another team is offering, what do you think?’ The no-trade clause was important, and being able to assure he’s going to be in one city.”

At the same time the Bears battled back from a 21-3 halftime deficit to beat Green Bay late — Bregman joked to Reagan that the timing of his deal “could go one of two ways” when remembered by Chicago fans — the third baseman’s agreement became public. As the Bregmans went to a celebratory dinner and then paid a visit to their neighbor and new Cubs teammate Jameson Taillon, Boston was reeling from the news. As fans began to square a Bregman-less future, the three-time All-Star began the process of contacting members of the Red Sox to say goodbye.

“I talked to all the players and the coaches and just expressed to them that it was an honor to take the field with them,” Bregman said. “They’re set up to be a really good team for a long time.”

At the outset of the offseason, the expectation was that the Red Sox and Bregman would eventually find mutual ground after striking a short-term pact – a three-year, $120 million deal that included opt-outs after both 2025 and 2026 — in February. As time wore on, though, the Cubs remained aggressive while the Red Sox seemed to play things a little slower. On Thursday, as he was introduced at Wrigley Field, the ever-political Bregman declined twice to discuss his negotiations with the Red Sox in much detail.

“Obviously, in free agency,” he said, “you talk to all the teams and figure out what they value.

“In free agency, you get to listen to the team’s needs. At the beginning of free agency, it was expressed to me how much (the Cubs) cared. The Cubs valued what I cared about. I’m looking forward to being here and winning baseball games.”

He was much more effusive about his new team.

“Literally, the first second free agency really opened, it felt like we knew the Cubs wanted our family to be here,” Bregman said.

“We had a lot of conversations over the course of the first three months of the offseason. Numerous calls with Scott and Jed. In our Zoom, it was pretty evident they wanted me to be here.”

The Red Sox’ offer was for less money, both in terms of overall total and net present value, than the Cubs’ final bid. It remains unclear if, with all else equal, Bregman would have taken that offer had the Red Sox made further concessions. The Cubs’ inclusion of the no-trade clause, though, was clearly a difference-making negotiating tactic, something Bregman himself acknowledged Thursday. (The Red Sox have not given out a no-trade clause in a contract under Craig Breslow or his predecessor, Chaim Bloom. Chris Sale received one from Dave Dombrowski in the five-year extension he signed in March 2019).

“Being able to be in a place that offered stability and a place that showed how much they cared about me is super important to me and my family,” Bregman said. “I have a young family and we can’t wait to raise our kids here in Chicago.”

Bregman’s familiarity with the Cubs from their failed pursuit last year — “more background and a little more knowledge of the organization than might happen if it was a cold call,” Hoyer said — helped inform Bregman’s process from the start. As he took Zoom calls with different teams, he appreciated how the Cubs valued his leadership qualities and viewed him as a player that could push them over the edge after a 92-win season in 2025.

The relationship between Bregman and his future team was solidified Saturday in the form of a half-decade agreement, but had grown in the months prior.

Bregman said he didn’t know Saturday would be decision day when he woke up, but that he had considered the Cubs a real threat from the beginning of free agency. Instead of waiting until spring training to sign like he did a year ago, Bregman wanted to get a deal done earlier.

“I thought it was trending that way, probably from the beginning of the offseason,” he said. “They expressed right away that they wanted me and they made it extremely clear that they valued what I offered.”

“It was definitely a little bit different,” he said of the whole process. ”I felt like everything was coming together a lot quicker and coming quicker together.

Bregman, who attended a Blackhawks game Monday and a Bulls game Tuesday as he arrived in Chicago for a physical and press conference, took time to thank Red Sox fans in an Instagram post Wednesday night. While his time in Boston was short, it was still a meaningful period for a player looking to challenge himself after an nine-year run with the Astros came to an end.

“The thing that I’ll take away is winning and getting to the playoffs,” Bregman said. “Scott mentioned it earlier, but it was a young group of guys and not many people expected us to get to the playoffs. We got to the playoffs. I feel like the guys on the team got a lot better at the game of baseball. Definitely will always cherish the support from the Boston fans.”

For the Red Sox, who pivoted quickly and agreed to a five-year, $130 million contract with another Boras client, Ranger Suárez, on Wednesday, the Bregman decision came as a major disappointment.

“He had a great experience in Boston,” Boras said.” He really enjoyed working with everybody in the organization, frankly. They were all people who did things really, really well for him. But sometimes, people make decisions. My job is to give them the choices.”