Saturday night was a momentous occasion for Chicago sports enthusiasts. As they witnessed Caleb Williams and the Bears achieve an astonishing comeback victory in the second half against their long-time rivals, the Green Bay Packers, news broke that the Cubs had finalized a five-year, $175 million contract with third baseman Alex Bregman, according to multiple sources reported by MLB.com.
Bregman, a three-time All-Star and two-time World Series champion, joins a Cubs team eager to reclaim its former glory in the NL Central and possibly aim for another World Series title, nearly a decade after their last championship in 2016.
Here are five key insights from this significant deal:
Bregman's Strategic Opt-Out Clause
Bregman's decision to negotiate an opt-out clause after the first year of his contract with the Red Sox last season has proven to be a clever move. Recall that he struggled during the 2024 season, hitting only 26 home runs and posting a .315 on-base percentage—the lowest of his career. This was a player who had once finished second in the AL MVP voting in 2019 but seemed far removed from that form.
Despite facing some injury challenges in 2025, Bregman showed signs of a resurgence this past season, achieving his highest batting average (.273) and slugging percentage (.462) since 2019. He successfully leveraged this comeback to secure a long-term position with the Cubs.
This highlights an important lesson for players: don’t hesitate to invest in your own potential, as Bregman’s strategy clearly paid off.
Are the Brewers’ Skeptics Finally Justified?
For several years, many baseball analysts, myself included, have been made to look foolish for doubting the Brewers’ capabilities; they have won three consecutive NL Central titles and four of the last five. However, following Bregman’s signing, it’s difficult to argue against the notion that the Cubs are now the favorites for the division title in 2026.
Adding Bregman to play third base and bolstering the lineup—alongside the addition of Edward Cabrera to the rotation and several new bullpen arms—shines a spotlight on the Brewers’ relatively quiet offseason. They have not made any impactful signings, traded away Isaac Collins, and rumors are swirling about Freddy Peralta potentially being on the trading block. The Brewers have relied on a streak of good fortune over the past few years, especially in 2025, to maintain their success. But can they keep evading misfortune indefinitely?
The Cardinals’ Trade Strategy for Brendan Donovan is Clearer Now
There has been a fair amount of unease among Cardinals fans regarding the presence of both Brendan Donovan and Nolan Arenado on the roster. While Sonny Gray and Willson Contreras were traded to Boston before the new year, many have wondered if the team's rebuilding efforts have hit a snag.
However, it seems that team president Chaim Bloom was biding his time, waiting for Bregman to sign. With the Diamondbacks having taken Ketel Marte off the market and Bo Bichette likely next to secure a deal, Donovan emerges as a prime candidate for teams looking to bolster their infield offense and defense. The Mariners appear to be the most logical fit, giving Bloom various avenues to maximize trade value.
Another interesting aspect: the next most attractive trade option at third base could be Arenado. Although he might not yield a significant return, moving him could open opportunities for Nolan Gorman to finally make a mark in St. Louis. In a way, the Cubs’ acquisition of Bregman may have inadvertently facilitated the Cardinals’ offseason plans.
Red Sox Must Take Action—But What Are Their Options?
The Red Sox’s decision to trade Rafael Devers last June received widespread acclaim, including from myself, as a strategic move to clear future payroll space for more judicious spending to support their young talent. However, Red Sox fans must now be wondering when this anticipated spending will begin.
The remaining free agents on the market don’t align well with the Red Sox's needs. Since they already have enough left-handed outfielders, the fact that two of the best available players, Kyle Tucker and Cody Bellinger, fit that profile poses a challenge. With Marte off the table and the likelihood of missing out on Bichette, especially with the Phillies making aggressive moves to secure him, the Red Sox risk finishing the offseason without meaningful acquisitions.
Given the flurry of activity from other teams in the division—excluding the Yankees—this situation could spell trouble for them moving forward. It's important to note that there are alternative methods to strengthen the roster beyond just pursuing trades with the Cardinals.
Cubs Fans Finally Get What They've Been Anticipating
As mentioned earlier, it has been a full decade since the Cubs clinched the World Series, an event that remains one of the most significant milestones in baseball during this century. (Yes, the Cubs won the World Series! It still feels surreal to say it aloud!)
However, since that historic win, Cubs fans have faced disappointment. The team has yet to return to the Fall Classic, despite boasting a talented roster that initially sparked hopes of a dynasty, which was then gradually dismantled.
Though they have shown some improvement recently, the Cubs have finished second to the Brewers in the division for the past three seasons, including the last two since hiring Milwaukee’s former manager. Yet, since 2016, the Cubs have refrained from flexing their financial muscle, with the only notable free-agent signing being Dansby Swanson three years ago.
The acquisition of Bregman signifies a shift in the Cubs’ approach, indicating they are finally recognizing their potential as a dominant force in the NL Central—a status their fans and many others have believed they deserved all along. With the Cardinals undergoing a rebuilding phase, the Cubs seem poised to reclaim their status as frontrunners in the division.
