Thursday’s introductory press conference made clear how the Chicago Cubs separated themselves from the Boston Red Sox in the Alex Bregman negotiation.
By the time Alex Bregman sat with his family in Arizona on Saturday morning, the decision had become much simpler than dollars and deferrals.
This wasn’t about a final counter or leverage. It was about certainty - where to live, for how long, and the stability of the next career phase.
That contrast - certainty versus structure - set the Cubs apart from the Red Sox.
Chicago pursued Bregman early and persistently after missing out the year before. Boston stayed engaged, sticking to their valuation. By the weekend, the choice was clear: Boston offered five years at $165 million with heavy deferrals and no trade protection; Chicago countered with $175 million, simpler finances, and a full no-trade clause.
As Bregman’s agent Scott Boras explained during Thursday’s introductory press conference for Bregman at Wrigley Field, the process was intentionally stripped down.
“Where are you at?” was the question posed to both clubs.
Not emotionally. Not hypothetically. Just plainly.
Chicago responded by showing unwavering commitment, while Boston's reply relied on disciplined structure.
The difference wasn’t subtle.
For Bregman, the no-trade clause was essential. After nine years in Houston and a year proving himself in Boston, he wasn’t seeking another short-term stint. He and his wife Reagan wanted stability for their young family and assurance that the team would not pivot unexpectedly.
That concern was grounded in Boston’s recent history. Leadership has changed quickly, philosophies have shifted, and assets have become flexible. Under Craig Breslow, Boston has valued discipline, control, and long-term optionality. This shaped every negotiation point - from deferrals to trade protection refusals.
Jan 15, 2026; Chicago, Illinois, USA; Catrina Connelly Patrick Connelly and baby Declan pose for a photo outside of the Chicago Cubs marquee announcing the Cubs new player Alex Bregman. (David Banks/Imagn Images)Chicago, in contrast to Boston, took the opposite approach: prioritizing certainty and permanence over flexibility and future options.
As Boras explained Thursday, after dissecting net present values and deferral math, the Cubs’ proposal offered what Boston refused: permanence. When Jed Hoyer presented the improved offer, negotiations accelerated. There was no prolonged standoff. No last-minute scramble.
As the Bears completed a comeback against the Packers at Soldier Field, Bregman made the call.
Afterward, the aftermath was subdued: a celebratory dinner, a visit with new Cubs teammate Jameson Taillon, then the emotional calls to Red Sox teammates and coaches.
“It was an honor to take the field with them,” Bregman said Thursday.
And that wasn’t lip service. His year in Boston mattered. He embraced the leadership role. He thrived in Fenway’s daily intensity. He helped guide a young roster to the postseason despite modest expectations. For a player still navigating the long shadow of 2017’s cheating scandal, Boston represented growth and challenge.
But alignment mattered more than appreciation.
At his introduction, Bregman avoided details about the Red Sox talks and focused on why Chicago appealed.
“They expressed right away that they wanted me,” said Bregman on Chicago’s pursuit. “They valued what I cared about.”
That message was clear from the first moments of free agency: frequent calls, Zooms, a shared vision, and familiarity from last year’s pursuit. By Saturday, the Cubs weren’t just competitive - they were trusted.
Boston, meanwhile, stayed true to itself.
They didn’t misread Bregman’s value. They didn’t disappear. They didn’t panic. They negotiated exactly as they intended. But that discipline came with a cost. Once the Cubs’ offer was presented as a fait accompli, there was no counterpunch waiting in the wings.
For Red Sox fans, disappointment was real.
But they pivoted quickly, committing five years and $130 million to Ranger Suarez, doubling down on pitching after losing their top offensive target.
Bregman didn’t leave because Boston refused to spend.
He left because, when forced to choose between flexibility and commitment, the Red Sox prioritized flexibility, while Chicago valued commitment.
Jan 15, 2026; Chicago, Illinois, USA; L-R Scott Boras, Alex Bergman and Jed Hoyer as Bregman is introduced as a new Chicago Cubs player at a press conference at Wrigley Field. (David Banks/Imagn Images)JOIN THE CONVERSATION:
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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.