How Chicago Cubs landed the star third baseman

Alex Bregman pulled on his crisp, pinstriped Chicago Cubs jersey, flashing a new number for the first time in his decade-long big-league career.

Bregman did not bother asking teammate Nico Hoerner if he could get the No. 2 the Cubs second baseman also has worn throughout his time in the majors. Instead, Bregman felt inspired to select the number signifying the third World Series title he wants.

Bregman’s life centers on two things: his family and winning games.

Column: Long, strange free-agent trip for new Chicago Cub Alex Bregman — and Scott Boras — ends in Wonderland

Those were the driving forces behind his free-agent process that ultimately led him to the Chicago Cubs. After failing to sign the third baseman last spring, unable to meet the value and one-year opt-out he received from the Boston Red Sox, the Cubs made sure Bregman had no doubts this time as to how much they wanted him in a Cubs uniform and the lengths the organization would go to make that happen.

“Literally the first second that free agency really opened I felt like we knew the Cubs wanted our family to be here, and we were excited about it,” Bregman, 31, said. “I thought it was trending that way, probably from the beginning of the offseason. They expressed right away that they wanted me. They made it extremely clear that they valued what I valued.”

An hour before the Chicago Bears’ playoff game against the Green Bay Packers on Saturday night, both sides were getting into the final details of the deal. Bregman’s wife, Reagan, started looking at places to live in Chicago with their two boys, Knox and Bennett, and then went out to dinner in Arizona to celebrate. The news of Bregman’s five-year, $175 million contract was finalized early in the fourth quarter as the Bears mounted their incredible comeback win. A grinning Bregman recalled that when the deal broke as the Bears trailed 21-6, he thought, “This could go one of two ways, I hope they come back.” Bregman will be at Soldier Field for Sunday’s game against the Los Angeles Rams.

President of baseball operations Jed Hoyer hadn’t planned for everything to come to fruition, either, during the Bears’ big win, which he watched at home with his sons.

“You never quite know when deals are going to get done — it wasn’t ideal timing, but it ended up kind of perfect,” Hoyer said. “We’re always balancing dollars this year, dollars next year, you always try to put that puzzle together, but I think certainly the goal going in was we knew we had to redo the bullpen because we had all the guys on the one-year deal, and we wanted to add a clear upgrade in the rotation, and we wanted to improve our offense.

“Adding depth to our roster is still something that we’re going to be focused on, so by no means are we done with the offseason, but I do think that we check some of the big boxes that we were hoping to accomplish.”

New Cubs third baseman Alex Bregman puts on his jersey between agent Scott Boras, left, and President Jed Hoyer at his introductory news conference Thursday, Jan. 15, 2026, in Chicago. (E. Jason Wambsgans/Chicago Tribune)

The Cubs never wavered in expressing their interest to Bregman and agent Scott Boras to the point of making offers fairly early.

Bregman had been on Hoyer’s radar since the third baseman was an amateur standout in New Mexico. The Red Sox drafted Bregman in the 29th round in 2012, about seven months after Hoyer left to become Cubs general manager. Following a stellar career at LSU, Hoyer hoped Bregman might drop with the Cubs picking ninth in the 2015 draft, the spot where they took Ian Happ, but the Houston Astros selected Bregman second behind top pick Dansby Swanson. Bregman’s former manager in Houston and current Tigers manager A.J. Hinch is a good friend of Hoyer’s from their time together in San Diego, resulting in further insight into Bregman over the years.

“The incredible intensity every single day, in the video room, in the cage trying to develop a plan to win that night, so I felt like I had pretty good inside knowledge of what he brings,” Hoyer said. “He’s a player that I’ve kind of followed. Never really had a great opportunity to acquire him, but certainly always admired him from afar because of how he plays a game and how he prepares and also how people around him talk about him, which is really important.”

One of the biggest separators within the competing interest Bregman received from the Red Sox and Cubs was each team’s willingness to do something the organization typically tries to avoid. Most notably, the Cubs were willing to construct a contract with deferrals — $70 million total of the $175 million contract — something they had opposed organizationally in recent years. A change in their philosophy can be traced back to the summer when Hoyer’s conversations with Chairman Tom Ricketts and president of business operations Crane Kenney highlighted the merits of doing those type of contracts. The Cubs were willing to give Bregman a no-trade clause, which the Red Sox avoid and ultimately wouldn’t include for Bregman.

“The two most important things to me are my family and winning baseball games, and the Cubs showed me right away that they were committed to both of those things,” Bregman said.

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