The Chicago Cubs entered the 2025 offseason with clear intent.
Fresh off an impressive campaign that reestablished them as a legitimate National League contender, the organization was determined not to waste momentum or rely on internal optimism alone.

Instead, the Cubs’ front office approached the winter with aggression and clarity.
Their strategy was simple yet ambitious: reinforce weaknesses, deepen the roster, and ensure that the success of 2025 would not be remembered as a fleeting peak but a foundation.

Across Major League Baseball, few teams were as active or deliberate as Chicago.
From bullpen reinforcements to high-impact acquisitions, the Cubs consistently appeared in transaction headlines, signaling to both fans and rivals that they were serious about sustained contention.

One of the earliest areas addressed was the bullpen, a unit that showed flashes but lacked consistency during critical stretches.
Chicago responded by adding multiple experienced arms, prioritizing depth, flexibility, and situational reliability over a single headline name.

Veteran right-hander Phil Maton was among the first signings, bringing postseason experience and a reputation for handling high-leverage innings.
His addition immediately stabilized the middle-relief picture and offered manager Craig Counsell more late-game options.

The Cubs also secured Hunter Harvey, a power arm capable of missing bats at an elite rate.
Harvey’s velocity and slider-heavy arsenal added a different look to the bullpen, something Chicago lacked in crucial late innings.

Left-handed depth was addressed with the signings of Caleb Thielbar and Hoby Milner.
Both pitchers bring matchup flexibility, particularly against tough left-handed hitters in high-pressure moments.

To round out the bullpen overhaul, Chicago added Jacob Webb, a quietly effective arm with the ability to bridge innings.
Collectively, these moves transformed the bullpen from a question mark into a potential strength.

The Cubs did not limit their efforts to free agency alone.
In a calculated trade with the Miami Marlins, Chicago acquired right-hander Edward Cabrera, a pitcher with electric stuff and untapped upside.

Cabrera’s raw talent has never been in doubt, but consistency has remained elusive.
The Cubs believe their pitching development infrastructure can unlock his potential, making the trade a classic high-upside, moderate-risk investment.

Yet despite all these moves, none generated as much attention as Chicago’s blockbuster signing late in the offseason.
The Cubs stunned the league by agreeing to a five-year, $175 million contract with star infielder Alex Bregman.

Bregman’s arrival instantly reshaped the Cubs’ infield and their offensive ceiling.
A three-time All-Star with championship pedigree, he brings postseason experience, elite plate discipline, and a reputation as one of baseball’s most cerebral players.

Defensively, Bregman is expected to handle the left side of the infield alongside shortstop Dansby Swanson.
The pairing reunites two players whose baseball paths have crossed repeatedly over the past decade.

Swanson and Bregman first built chemistry years ago while representing Team USA during their amateur careers.
Both later starred in the SEC and became the No. 1 and No. 2 overall picks in the 2015 MLB Draft, respectively.

Their shared history adds an intangible element to the signing that extends beyond metrics or contract value.
It is a reunion built on familiarity, mutual respect, and a deep understanding of how each approaches the game.

Speaking recently, Swanson made it clear that he is thrilled to once again share a clubhouse with Bregman.
More importantly, he believes Bregman’s presence will directly elevate his own performance on the field.

According to Patrick Mooney of The Athletic, Swanson spoke candidly about the impact Bregman could have on his game.
His comments revealed admiration not just for Bregman’s talent, but for the way he processes baseball situations.

“Alex is somebody that I’ve admired for a long time,” Swanson said.
“Who he is, how he plays, and the things that he sees make me feel my game could benefit more from playing with him than almost anyone else.”

Swanson was careful to clarify that his comments were not a slight toward past teammates.
Rather, he emphasized that Bregman possesses a rare perspective, one shaped by experience, preparation, and an elite understanding of nuance.

Bregman’s reputation as a student of the game is well established across MLB circles.
He is known for meticulous video study, pitch recognition, and an advanced approach that blends analytics with instinct.

For Swanson, that intellectual edge is just as valuable as Bregman’s on-field production.
He believes constant exposure to that mindset can sharpen his own decision-making, anticipation, and overall baseball IQ.

Swanson went a step further, suggesting that Bregman could actively challenge him to improve.
That challenge, he implied, would be rooted in accountability, preparation, and a shared desire to push standards higher.

These remarks resonated strongly with the Cubs fanbase, eager to see leadership take shape organically within the roster.
Championship teams, after all, are often defined by internal competition and players who demand excellence from one another.

From an organizational standpoint, the Cubs see this pairing as foundational.
Swanson and Bregman are not just stars, but tone-setters capable of influencing younger players across the clubhouse.

The ripple effects could be particularly significant for Chicago’s emerging infield talent.
Daily exposure to two elite defenders with complementary skill sets provides an invaluable learning environment.

Offensively, the Cubs expect Bregman’s presence to lengthen the lineup and protect key hitters.
His ability to grind at-bats and reach base consistently should create more run-producing opportunities throughout games.

Looking ahead to the 2026 season, expectations around Wrigley Field are steadily rising.
With a fortified bullpen, added pitching upside, and a retooled infield, the Cubs believe they are positioned to contend deep into October.

The Swanson-Bregman partnership stands as a symbol of that ambition.

It represents more than a roster move; it reflects a philosophical shift toward intelligence, preparation, and sustained excellence.

If their chemistry translates as expected, Chicago may have assembled one of the most impactful infield duos in the National League.
For a franchise chasing its next championship window, that possibility alone is enough to generate genuine excitement.