Alex Bregman’s Cubs Signing: Family and Winning Seal the Deal

Alex Bregman officially wore the Chicago Cubs’ pinstriped jersey for the first time, choosing number 3 to symbolize the third World Series championship he aims to win. The move marks a significant shift in his career that focuses on two guiding principles: prioritizing his family and striving for victory on the field. This blend of personal and professional commitment motivated Bregman’s decision during the free-agent period, leading to a lucrative and long-anticipated contract with the Cubs.

The Negotiation Process and Cubs’ Demonstrated Commitment

After negotiations stalled last spring with the Boston Red Sox because of disagreements over contract value and opt-out terms, the Cubs intensified their pursuit this offseason. They clearly conveyed their strong desire to have Bregman wear their uniform, leaving no room for doubt about their intent. Bregman recalled,

“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,”

underscored by the Cubs’ alignment with his values, especially regarding family and winning.

As the Chicago Bears played a memorable playoff game against the Green Bay Packers on a Saturday night, Bregman was finalizing his five-year, $175 million contract. His wife, Reagan, was already scouting Chicago neighborhoods for their sons Knox and Bennett. When the deal was announced with the Bears trailing, Bregman noted,

“This could go one of two ways, I hope they come back.”

Indeed, the Bears overcame the deficit, adding a sense of celebration to the signing.

Alex Bregman
Image of: Alex Bregman

The Cubs’ Front Office Perspective on the Signing

Jed Hoyer, the Cubs’ president of baseball operations, admitted the timing of the deal’s completion wasn’t planned but called it “kind of perfect.” Watching the Bears’ comeback at home with his sons, Hoyer described the front office’s balancing act of finances and roster needs this offseason. He explained the strategic goals involved, stating,

“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.”

Although the Cubs still intended to add depth elsewhere, Hoyer emphasized that signing Bregman addressed some of their critical objectives. The organization’s steadfast focus on securing Bregman from the early stages was evident, shaped by a longstanding interest dating back to his amateur days. Hoyer first noticed Bregman while the latter was a standout player in New Mexico, further strengthened by connections in the baseball community, including A.J. Hinch, former manager of Houston and current manager of Detroit Tigers, a longtime confidant of Hoyer’s.

Bregman’s Attributes and the Cubs’ Contract Flexibility

Bregman’s reputation for intense daily preparation and leadership resonated deeply with Chicago’s clubhouse culture. Hoyer praised,

“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.”

The Cubs’ willingness to adapt their contract structure became a critical differentiator, notably agreeing to $70 million in deferrals and including a no-trade clause, which the Red Sox declined to offer.

The shift in Chicago’s approach resulted from conversations involving Hoyer, Chairman Tom Ricketts, and president of business operations Crane Kenney, who evaluated the advantages of such contracts. Bregman himself appreciated the Cubs’ commitment to his values, stating,

“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.”

Projected Impact and Team Dynamics Within the Cubs’ Infield

Analyzing Bregman’s future with the team, the Cubs evaluated his skill set as well-suited for longevity despite the natural aging curve. His elite strike zone control, consistent contact abilities, disciplined preparation, and leadership qualities were all factors convincing the front office of his value over five years. Bregman described the team environment as

“a group of guys that are focused on getting better at the game of baseball every single day and want to be the best version of themselves, and that’s the kind of group that you need.”

He also emphasized the Cubs’ transparency about improvement plans and their dedication to maintaining a winning standard throughout his contract:

“When talking with the Cubs this offseason, they told me ways that I could get better as a player, ways that they were planning on making improvements to their team, how committed they were to winning, how that will be the standard here, and how it will be the standard every year that I will be here.”

The addition of Bregman affects other infielders’ roles, especially Matt Shaw, the third baseman who was a Gold Glove Award finalist last year. With the Cubs effectively fielding five starting-caliber infielders, trade talks have emerged, though Jed Hoyer remained circumspect about any moves or discussions.

“There’s always calls coming in, I think it’s an active industry where people are always looking at those things,”

he said.

“But it’s our job to listen to things, that’s always our job, and it’s always our job to seek to make the team better. It doesn’t mean we’re looking to do something, but of course people are going to call, and the job is to listen and to think about it.”

The Significance of Bregman’s Signing for the Cubs’ Future

Alex Bregman’s arrival signals the Chicago Cubs’ ambition to solidify their roster with proven talent committed to both personal values and team success. The contract’s combination of financial commitment and contractual flexibility demonstrates a strategic shift in how the Cubs operate, balancing long-term planning with a desire to remain competitive immediately. For Bregman, joining this organization means immersing himself in a culture focused on continual improvement and winning championships, while also providing for his family.

This signing is expected to reshape the infield’s landscape, possibly triggering player movements and depth reshuffling. As the team prepares for the upcoming season, Bregman’s role as a leadership presence and offensive contributor will be closely watched, especially in the context of the Cubs’ broader goals for regaining prominence in Major League Baseball.

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