When you look at the details Alex Bregman choosing the Boston Red Sox over the Chicago Cubs, it’s not all that surprising. The Red Sox have been sitting on the sidelines for too long, watching the New York Yankees and Baltimore Orioles build stronger rosters while they struggled to define their direction. Signing Bregman isn’t just about bringing in a star player—it’s about making a statement that Boston isn’t going to keep playing the middle ground.
For the last few years, the Red Sox have been one of the most frustrating teams in baseball, especially for their fans. They’ve refused to go into full rebuild mode, yet they also haven’t spent aggressively to compete at the highest level. They traded Mookie Betts to the Los Angeles Dodgers in 2020 and didn’t do much to replace him. They let Xander Bogaerts walk in free agency after 2022, and their biggest move to compensate for that was locking up Rafael Devers long-term. While Devers is undoubtedly a cornerstone piece, Boston didn’t do much to surround him with other top-tier talent. Their offseason moves have mostly been about maintaining competitiveness rather than truly contending. They signed Trevor Story, but injuries have prevented him from being the impact player they expected. They picked up Justin Turner and Adam Duvall for short-term deals, but those weren’t the kinds of signings that were going to change the franchise’s trajectory.
Meanwhile, their division rivals have been aggressive. The Yankees have never been shy about spending, and even when some of their big moves haven’t worked out, they’ve at least tried to put a winning roster together. The Orioles have taken a different approach, relying on their deep farm system to build a young, talented core that could make them a powerhouse for years. While those two teams were making strides, the Red Sox were stuck, seemingly unwilling to pick a direction. Were they going to go all-in and spend to compete, or were they going to tear things down and start over?
Signing Bregman finally gives some clarity to that question. They’re trying to win. It’s an expensive move—$40 million a year is no small commitment—but it’s the kind of move that elite teams make when they believe they can compete. The Red Sox didn’t just pay for Bregman’s talent; they paid for his leadership, his experience, and his ability to help them keep up in an increasingly competitive AL East.
One of the biggest talking points surrounding this deal is Bregman’s position change. With Devers entrenched at third base, the Red Sox had no choice but to shift Bregman to second. It’s not unheard of—he played shortstop in college and early in his pro career—but it’s still a major transition. Third base and second base require different skill sets. Third base is all about quick reactions and strong throws, while second base involves more range, different footwork, and being comfortable turning double plays from different angles. The Red Sox clearly believe he can handle the transition, but it won’t be without challenges.
If this works out, Boston gets an elite bat in the middle of their infield and another strong veteran presence in the clubhouse. If it doesn’t, they could find themselves stuck with an expensive player in a role that doesn’t quite fit. That’s the risk they’re taking, but after years of playing it safe, it was a risk they needed to take.
Bregman’s offensive production is another key factor here. He’s no longer the MVP-level player he was in 2018 and 2019, but he’s still a highly productive hitter. Over the last couple of seasons, his wRC+ has hovered around 120, meaning he’s about 20% better than the league average at creating runs. That’s not quite elite, but it’s still very good. He’s also maintained strong plate discipline, consistently posting high walk rates and low strikeout rates. His power numbers have fluctuated, but even in a slightly down year, he’s still a threat at the plate.
For Boston, this isn’t just about what Bregman does on his own—it’s about what he does for the rest of the lineup. Devers has needed help. For too long, opposing teams have been able to pitch around him because the Red Sox didn’t have enough firepower elsewhere. Adding Bregman changes that. It forces pitchers to be more aggressive against Devers, knowing there’s another dangerous hitter behind him. It lengthens the lineup, giving Boston more consistency and making it harder for opposing teams to navigate their order.
It also sends a message. For years, the Red Sox front office has operated as if they weren’t quite sure whether they wanted to go for it or take a step back. This move makes it clear—they’re going for it. They’re not just trying to scrape into the playoffs; they’re trying to compete with the Yankees and Orioles for the division. That’s a big shift from where they’ve been the last couple of seasons.
That’s not to say this move solves all of Boston’s problems. They still have some question marks in their rotation, and they’ll need other players to step up for them to truly be a threat in the AL. But signing Bregman is a sign that they’re serious about competing. They could’ve sat back and continued to make mid-level moves, hoping things would work out. Instead, they made a bold move that puts them back in the conversation as a team to watch.
For Bregman, this is a perfect situation. He gets a massive contract with opt-outs, meaning he controls his future. If he plays well, he can test the market again and potentially land another big deal. If things don’t go as planned, he still has financial security. And on top of that, he gets to play in a big market with passionate fans, on a team that is actively trying to win.
This also isn’t the first time Bregman has played with a chip on his shoulder. He’s been one of the most polarizing players in baseball since the Astros’ sign-stealing scandal came to light. He’s embraced that role, thriving as a player who loves to prove people wrong. In Boston, he’ll get a fresh start, but he’ll also be in a city that demands results. If he performs, he’ll be beloved. If he struggles, he’ll hear about it. That’s the nature of playing in Boston, and it’s a challenge he seems built for.
What remains to be seen is how this move impacts the balance of power in the AL East. The Yankees aren’t going anywhere, and the Orioles are only going to get better. The Rays always seem to find a way to be competitive, and even the Blue Jays have the talent to be dangerous. The Red Sox had to do something to keep up, and signing Bregman is a big step in that direction.
This move also puts pressure on the Red Sox front office to keep building. Signing one star isn’t enough—they need to continue adding pieces. If they stop here, they might find themselves in the same spot they’ve been in recent years: good, but not great. But if this is just the beginning of an aggressive push to strengthen the roster, the Red Sox could quickly go from being an afterthought in the AL East to a legitimate contender.
Here’s the thing folks: The Bregman signing represents something bigger than just one player joining a new team. It’s about the Red Sox finally making a decision about their future. They’re not going to sit back and watch the Yankees and Orioles dominate the division. They’re not going to be stuck in mediocrity, making half-measured moves that don’t truly move the needle. They’re going for it.
With that… It’s up to Bregman to prove that he was worth the investment. If he plays like the star he’s been in the past, the Red Sox will look like geniuses. If he struggles to adjust to second base or his offensive production declines, they’ll have to live with the consequences of taking this gamble. Either way, Boston is finally making moves again, and that alone makes them a more interesting team heading into the season.
If you cannot play with them, then root for them!