Red Sox Sign Alex Bregman to Cap Brilliant Offseason

The biggest remaining free agent of the 2024-25 offseason is off the board. In a splashy signing Wednesday night, the Boston Red Sox and Alex Bregman agreed to a three-year, $120 million deal. There’s no shortage of things I want to say about this match of team and player, so let’s stop with this boring introduction already and get right into it.

The Team

The Red Sox needed Bregman, or someone like him, badly. Just one problem – there was no one else like him. When Dan Szymborski ran the numbers last week, he found that the Sox were one of the teams who would receive the greatest boost in playoff odds from signing Houston’s long-time third baseman. Per Dan, Bregman adds 10.8 percentage points to Boston’s chances of reaching October.

The Red Sox play in the toughest division in baseball. They have some holes in their lineup, particularly a decided lack of juice at the bottom of the order. Their bullpen projects well but is packed with uncertainty. A sure thing was just what they needed. Bregman is just that. Since his 2016 debut, he’s been the 10th-best hitter in baseball according to our measure of WAR. “Oh, but Ben, he’s old, he’s faded, he’s past his prime, no one cares about 2019.” Yeah, well, over the last four years, Bregman has been the 11th-best position player in baseball. So much for a decline phase.

Boston was running a luxury tax payroll of around $210 million before signing Bregman. After accounting for deferrals, his deal is going to bring them up to around $240 million, right around the first CBT threshold. But here’s another way of looking at it: For $210 million, which includes both free agents and players under team control playing at suppressed rates, the Red Sox had about a 44% chance of making the playoffs. That’s around $5 million per percentage point. Then they gave Bregman $30 million a year in present value for 10 percentage points. If you’re keeping score at home, that’s a rate of $3 million per one percentage point. That sounds pretty good to me.

That’s a great spot to know your leverage. The Sox were in the ideal position to keep adding. If they weren’t going all out to improve, you’d question the plan here. Rafael Devers and Jarren Duran are at their respective peaks. Several key contributors are on the wrong side of 30. The farm system is teeming with talent that should start hitting the majors soon, providing a stream of reinforcements. They just made a trade for Garrett Crochet. All the arrows were pointing toward getting better right now, and the Bregman deal represented the best way to do that. Full marks here.

The Positional Fit

The only obstacle to Boston’s bringing in Bregman, aside from a giant stack of Benjamins? Devers, the team’s incumbent third baseman, who might also be its best player and is certainly its most tenured star. Bregman has played almost his entire career at third base; he has spent 966 innings at shortstop, mostly as an injury replacement, as well as 32 at second and 3 2/3 in left field, but his last defensive appearance away from the hot corner came in 2019. He’s a very good defender, and Devers is a poor one, but you don’t just shove aside the well-compensated franchise star for no reason, so Bregman is likely going to play second base in 2025.

I think this change will work quite well. Bregman has consistently graded out well at third, but he’s missing the biggest tool that separates the best third base defenders from the pack: a cannon arm. Among third basemen, Bregman’s arm strength has ranked within the bottom quarter of the league for pretty much his entire career. Not to put too fine a point on it, but look at Bregman, and then look at Matt Chapman and Manny Machado, and try to guess who can throw a ball harder. You won’t be wrong.

Bregman was a good enough defender to overcome that natural limitation, but his lack of arm strength won’t be an issue at second base. He’s actually an above-average thrower for the keystone, and we already know he has great reflexes and instincts. There’s always some risk to having a player learn a new position in his early 30s, but Bregman has always felt a bit like a second baseman. Now he’s going to learn how to be one on a big stage.

The Park

It’s not true that Bregman is solely a creation of the Crawford Boxes in Houston. Sure, he’s an expert at yanking fastballs down the line and into the nearby bleachers, but for his career, he has a .364 wOBA at home and a .363 mark on the road, banging scheme and all. On the other hand, consider this: Bregman is the all-time leader in OPS at Fenway Park, minimum 80 at-bats, with a 1.240 mark. Point at the Houston splits all you want, this guy is designed to aim at the Green Monster.

It’s not just that he’s going to rack up extra home runs, though that’ll certainly be the case. It’s everything else about Fenway that really kicks things into overdrive. Bregman is a fly ball hitter, perennially among the league’s air-happiest ones. He’s also a pulled-fly ball hitter, and he’s not a particularly powerful one. He never runs a high barrel rate, never finishes above the middle of the pack in hard hit rate or exit velocity, and he certainly isn’t going to threaten Ted Williams’ red chair anytime soon. That means plenty of mid-distance balls in the air, and many of those to left field.

That’s absolutely perfect in Boston, even more so than in Houston. The Monster’s outrageous proportions and his in-the-air-to-left approach will create off-the-wall singles and doubles in droves. That huge right-center power alley? Candidly, Bregman isn’t going to be bothered by it, because he doesn’t hit home runs even to shallower opposite-field alleys. He’s hit only 14 opposite-field homers in his career, and only three in the last five years.

Will this be a huge difference? Probably not, because no stadium can make that big of a difference. But Boston is tailor made for Bregman’s skills. That surely had an impact on his choosing to play there – and on the team making him this offer.

The Deal

It’s a fancy one! Three years and $120 million, with deferrals that, per ESPN’s Buster Olney, make it the equivalent of $90 million in non-deferred money. Bregman also gets an opt out after every year, which will theoretically let him dip back into free agency at his own discretion if he roars back to MVP contention at any point.

There were multiple competing offers on the table. The Astros were reported to have offered Bregman $156 million over six years, $26 million a year. The Tigers reportedly made an offer of six years and $171.5 million, $28.5 million per year. Those are princely sums, meaningful money over meaningful years, and throughout the offseason, Bregman reportedly was not interested in signing a short-term contract. Through that lens, then, those other offers seemed to be about what he was looking for, even if the AAV was less than what he wanted. That Bregman ultimately opted for the Boston deal despite those stated wishes tells me that he values flexibility and also likes to bet on himself — and that $40 million AAV was surely a factor.

Modeling two opt outs is meaningfully more difficult than modeling one, because the existence of the second changes the calculus on the first. That said, I took a crack at it using a modified version of my old Monte Carlo method. That tells me that Bregman has about a one-in-three chance of exercising his year-one opt out, and a 45% chance of leaving after the second year. I have both odds lower, myself, and I think that this particular situation is a tough one to model, so don’t take that as gospel. The point is that the path of least resistance is for him to stay – on a big salary for a championship contender – but it’s not set in stone.

That’s how I’d look at this deal. Most likely, Bregman will be in Boston for three years and make $120 million. If he’s better than expected this year – a fringe MVP candidate, or perhaps just short of that – he might be tempted to leave. If he’s much better than expected – a top-three player in the AL – he’ll opt out for a new deal somewhere, perhaps in Boston. That feels like a good assessment of the possible outcomes, and it explains why Bregman picked this deal over some other attractive ones: He thinks those upside scenarios are worth chasing.

The Player

That brings us to the part of this I’m most excited to write. Alex Bregman is working on a Hall of Fame career right now. It’s far from certain – some of his peak will be written off as a product of his knowing what pitch was coming – but at 40 WAR through age 30, he’s certainly knocking on the door of Cooperstown. The biggest obstacle to that is the inevitable onset of aging. His 2024 season was his weakest since his injury-marred 2021, and thanks to the crushing conformity of linear time, he’s older now than he was then – older than in any previous season, in fact. (What a concept!)

The signs of a slowdown are there. Bregman’s walk rate plummeted in 2024. He pulled fly balls less frequently, which sounds like a symptom of a slower bat. However, in terms of tracked bat speed, last season he added more than a mile an hour from the second half of 2023, so maybe this isn’t quite an issue yet. Then again, he also posted the lowest xwOBA and wOBA of any full season; only his brief 2016 debut was worse. For a 30-year-old, those are at least yellow flags on the risk indicator.

My counterpoint is just this: Everyone has down years. The question comes down to whether you think Bregman is one of those players who comes along a few times a generation and continues to produces even as people point out that he doesn’t have the raw tools to keep it up. You can think of Mookie Betts, José Ramírez, and old friend Jose Altuve as contemporaries in this bucket, and Chase Utley and Dustin Pedroia as the previous generation’s models. Joe Morgan, Craig Biggio, I’m sure you can keep throwing in names from the past. Is Bregman one of these guys? I’m not sure, but nothing he’s done so far makes me think he won’t be.

Some players’ best skill isn’t any particular physical tool but rather a preternatural combination of coordination and ability to learn. For me, Bregman fits into that category. Even when he was an MVP candidate and functioning as the sneering heart of the league’s biggest villains, he was doing it without tremendous measurables. He’s never been an exit velocity standout. He doesn’t have blazing speed. What he does have is hand-eye coordination like you wouldn’t believe. Cool Papa Bell could turn off the lights and be in bed before the room got dark; Bregman could probably turn off the lights and then solve a Rubik’s Cube behind his back, which is less impressive but perhaps more useful in a baseball context.

Look at it this way: Could his lower walk rate and decrease in pull-side power be a sign that he’s on the downswing? Sure. He also just cranked 26 homers, racked up a batting line 18% better than average, and did it all with a balky elbow that limited him to 145 games, his second-lightest full season workload (stupid 2020, always messing with our stats). Pitchers flooded the zone against Bregman in 2024, and he didn’t make them pay enough to change their ways. I wouldn’t bet against him making an adjustment, though, because he always has before.

His greatest asset in making that adjustment is that hand-eye coordination, and it seems clear that he hasn’t slowed down in that aspect. His contact rate in 2024? Highest of his career. Baseball Savant measures “squared-up rate,” the percentage of contact that is hit almost as hard as it can be for a given speed of bat and ball. It’s a new statistic, with only two years of data, but Bregman has been in the 99th and 96th percentiles in those two years.

Everyone always worries about the little guys fading, because sometimes they do. When Pedroia hurt his knee at age 33, he never recovered. Utley had a short career despite a tremendous peak, though some of that short career was due to his not becoming an everyday player until his age-26 season. But those are just some of the potential paths. Biggio put up a ludicrous 20.8 WAR in his age 31-33 seasons, and another 12 after that. Bregman isn’t anywhere near the player Morgan was, so this is more about career trajectory than actual numbers, but half of Morgan’s WAR came after age 30, and his best two years came at 31 and 32. Betts is aging like a fine wine, though he’s only a year older than Bregman and thus it’s too soon to draw any conclusions there.

Do you think Bregman is one of these meteoric talents? I do. He has it, for lack of a better way of putting it. Can you see him smirking in a press conference after a big playoff win in Boston? Obviously you can. Can you see him casually taking to second base and competing for a Gold Glove? I can. Can you see him talking trash to everyone while he does it? It goes without saying.

Truthfully, maybe Bregman belonged at second base all along. That list of comparables is heavy on second basemen. Even the ones who aren’t, Betts and Ramírez, are kind of second basemen. It’s the position that most elevates coordination and instinct. You don’t need blazing speed or a big arm to play it well. If you have bad instincts, all the physical tools in the world won’t save you. Height might actually be a hindrance there.

Put simply, I love this deal. It’s about time for the Red Sox to start acting like one of the big kids, and this offseason has been deal after deal of them doing just that. “Stop playing for next year” has been an annual complaint in New England; it stops here. I want Bregman on a contender, a team with legitimate World Series hopes, so we can see his heel persona and flair for the dramatic on the biggest stage. Sure, there are risks to this signing – there always are – but the rewards are there too. If the Red Sox recapture their late-2010s form after six years in the wilderness, we’re going to remember Bregman as the guy who turned the tide, as in “the ills of trading Mookie Betts were washed away by signing Alex Bregman.” You can’t ask for much more out of an offseason acquisition.