Red Sox fans are parroting concerns long held by a hungry Cubs fanbase

After years of avoiding the top of the market and eschewing longer-term deals, the Chicago Cubs finally entered modern free agency by signing Alex Bregman. His five-year, $175 million deal is the antithesis of what the team's strategy has been under the combination of Jed Hoyer's front office and Tom Ricketts' ownership. It's the highest AAV ever given out by the team, and it features major deferrals, a team and agent-friendly tactic that, for whatever reason, the Cubs have been opposed to in recent years.

To say it was a breath of fresh air is an understatement. For Cubs fans, it was finally a fulfillment of the promise that being a big-market team entails. Bregman wasn't an absolute necessity, but the front office understood how good a fit he was and how much he could elevate the team for not just 2026, but years to come. For once, they found a player they liked and jumped to offer him something truly competitive that would also give Scott Boras another win. All without having to trade Nico Hoerner.

Moreover, in signing Bregman, they leapfrogged an incumbent whom just about everyone predicted would re-sign the third baseman. Just days before the deal broke, the Red Sox had reportedly made a more aggressive push to bring back Bregman after what essentially amounted to a one-year deal for 2025. The Cubs were beaten out by Boston last year because they weren't willing to go long-term at four years and $120 million, leaving their offseason feeling incomplete after the Kyle Tucker trade. Their final offer this time, which also included a no-trade clause, easily topped their financial rival's reported $165 million deal, and now has Boston fans echoing the concerns Chicago is all too familiar with.

Red Sox and Cubs fans are both familiar with a lack of spending

The Red Sox haven't had a terrible offseason, per se. They've added Sonny Gray, Willson Contreras, and Johan Oviedo in trades to bolster both their lineup and pitching staff. Yet, they haven't waded into free agency at all despite being in a similar spot to the Cubs, where a bit of big-market spending could capitalize on an otherwise good 2025 season and put pressure on a very competitive division.

Their relationship with long-term, high-dollar deals has also, like the Cubs, been contentious. Heading into 2026, Boston just edged out Chicago as the third-most valuable franchise in baseball at $4.8 billion, behind only the Los Angeles Dodgers and New York Yankees. Yet, rarely has that translated to the spending expected of fans. The Mookie Betts trade is perhaps the most egregious example of their unwillingness to pay up for top-level talent, shipping off a face of the franchise to the Los Angeles Dodgers in a deal that, in the long run, sent next to no value back to Boston.

Their last megadeal for a position player, Rafael Devers' 11-year, $331 million extension ahead of the 2023 season, is already a thing of the past. The superstar infielder was flipped to the San Francisco Giants last summer in a cost-cutting move. Bregman's signing soured the relationship with their franchise slugger, who was promised the chance to stay at third base. Now, both are gone, and Boston was left holding the bag again. A deal for Bo Bichette may be their best option now, but like Cubs fans are all too accustomed to, the attitude is more "we'll believe it when we see it."

It's easy to see how the Cubs could've wound up in the Red Sox's shoes. If Hoyer and Ricketts didn't break from their typical passivity, Bregman may have found his way back to Boston, while the offense would've been forced to take a step back and rely on prospects after losing Tucker's bat. Particularly after Tatsuya Imai signed in Houston, reports suggested he was all but destined to join a long list of almost Cubs or other seemingly perfect free agent fits like Bryce Harper, Carlos Correa, Corey Seager, Shohei Ohtani, Dylan Cease, and many more before him, whom the team wouldn't set the market on. It would've been what fans have come to expect after years of lackluster spending and salary dumps of beloved players like Yu Darvish and Kyle Schwarber.

Instead, they finally decided to put on their big boy pants and be the team on the other side for once. In doing so, they've passed the offseason with flying colors, adding a high-upside arm to the rotation in Edward Cabrera, spending $30 million to rebuild the bullpen, finding a promising bench player in Tyler Austin, and capping it off with a big bat and clubhouse leader in Bregman. That is the behavior of an organization that's going for it, one that fans have been starving for, and that Boston still needs to show they're capable of.