FORT MYERS, Fla. – The swaggering ballplayer and the once-proud baseball town consummated their relationship this weekend, an engagement that may only last one year, yet might prove too bountiful and beautiful for both sides to see it end.
Alex Bregman is a Boston Red Sox, and Sunday morning, the nagging details – What position will he play? Will he opt out of his $120 million, three-year deal after just one season? – could be back of mind. Certainly, there have been ideal fits between big-time free agent and a franchise willing to spend money.
Yet rarely has a player’s skill set – such as Bregman’s punishing statistics at Fenway Park – and peripheral contributions nestled so snugly together, like the Green Monster tucked above Lansdowne Street.
The Red Sox won four World Series championships since 2004 yet have missed the playoffs five of the past six years. Bregman has never missed out on them in eight full seasons with the Astros.
The twin flame has been lit.
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‘I’ve been fortunate to be in the playoffs the first eight years of my career,’ Bregman says Sunday morning at Fenway South, after a whirlwind 48 hours meeting teammates and staff, ‘and I plan on continuing to do that here.
‘I plan on winning here.’
A beacon for Boston
There is a certain glint Bregman gets in his eye, usually when he’s about to say something significant or do something otherworldly on the baseball field. He was a World Series champion in 2017 and 2022, but the sign-stealing scandal that dogged the ’17 champs – and ensnared Red Sox manager Alex Cora, then Houston’s bench coach – took much of that swagger away.
Audacity gave way to anodyne. Bregman and his teammates were mercilessly booed wherever they went, including Fenway Park, where the Astros eliminated Boston in 2017, 2019 and 2021, with Boston getting the upper hand on Houston on its way to the 2018 title.
But in Boston, the past seven years has seen a model franchise desiccated, now on its third general manager since then and with the growing sense that free agents did not seriously consider Boston a destination.
And why would they? Yoshinobu Yamamoto and Rōki Sasaki barely gave it a thought before they bolted to the Los Angeles Dodgers. The Red Sox were in the Juan Soto sweepstakes long enough to perhaps qualify for a cake with ‘At Least You Tried’ written in frosting.
A wild card lottery ticket in ’21 was the only campaign to break up a string of third- and last-place finishes. The Fenway ticket was now a soft one.
And as Bregman festered on the market, letting a six-year, $156 million deal with Houston grow stale on the shelf, the Red Sox’s sense of desperation kicked in.
Club chairman Tom Werner – he’s also chair of Liverpool Football Club – called agent Scott Boras at 3:30 a.m. London time. General manager Craig Breslow called Boras 13 times, the agent recalls. And owner John Henry got involved, bemoaning what the Red Sox have become – which might come as news to a fan base that sensed Fenway Sports Group grew indifferent to years of mediocrity while having eyes for their other sports holdings.
‘There was a bit of a charge, a bit of an onus to really return back to winning,’ says Boras. ‘And a conversation I had with John where he expressed a sincerity and more of a passion of saying that we’re missing something here that should be here, that has been here.
‘Something that’s been lost. And we have a strong intention to return it.’
Bregman, Cora believes, is the perfect messenger.
Cora calls everyone ‘kid,’ give or take, but Bregman is now 30, with a 2-year-old son, Knox, that already has Boras Corporation officials salivating at his swing. Wife Reagan, says Bregman, will start an executive leadership program at Harvard Business School with the family in Boston.
And Cora saw firsthand in his one year in Houston just what Bregman brings to a clubhouse, to a dugout, and throughout an organization
‘One thing he’s going to do: He’s going to challenge everybody here,’ says Cora. ‘He’s going to ask about pitch usage and swing decisions and scouting reports, the nutrition side of it.
‘Not in a bad way. He wants to learn, wants to be involved. In 24 hours, his teammates, the front office, the coaching staff has already seen what I’ve been talking about him a long period of time. This kid gets it.
‘He commanded my attention in 2017 and throughout the years, he’s kept evolving, getting better. For him, it’s his family, baseball and winning.’
A good time, not a long time?
The baseball piece will be nice enough. Bregman is a two-time All-Star, a Gold Glove and Silver Slugger winner, owner of an .848 OPS and that Fenway track record – 375 average, .490 OBP and 1.240 OPS in 21 games – everyone’s swooning over.
Yet even still, he could be gone in a year.
Despite his track record, Bregman opted to accept what Boras calls a ‘bridge contract,’ much like the half-dozen players he’s guided that way the past two years. In most cases, it works out famously for the recipient – just look at Blake Snell’s $182 million deal this year – but can create the impression the upcoming season may just be a waystation for the player.
It doesn’t have to be that way. Carlos Correa opted out with the Minnesota Twins only to return. Matt Chapman signed a bridge deal with San Francisco and ultimately signed an extension. Cody Bellinger remained with the Chicago Cubs before a trade to the New York Yankees.
Bregman – who has a passion for racehorses he shares with now-teammate Walker Buehler – is more than ready to bet on himself.
‘I believe in my ability,’ he says, that familiar glint returning to his eye with a nine-figure guarantee and a chance to show out for a new and ravenous baseball market.
‘And I look forward to proving it.’
That fortitude enabled him to forgo the $171.5 million contract offer from the Detroit Tigers, where both winning and offensive production in Comerica Park might have been harder to come by. While his $120 million guarantee has significant deferrals, the $40 million annual value is in the 95th percentile for multiyear contracts.
Still, turning down more than $50 million more in guaranteed money isn’t for the faint of heart.
‘You adhere to what the player’s about. There’s some players you’d never do this with,’ says Boras. ‘But with a guy like Alex Bregman, he’s just built with an understanding of himself, a confidence, he trusts his preparation.’
Sunday, Bregman seemed both relaxed and edgy, playfully tossing a Red Sox cap on agent Boras’s head, looking nearly starry-eyed mentioning how his favorite player – Red Sox legend Dustin Pedroia – calling him several times to recruit him, along with current Red Sox shortstop Trevor Story.
These Red Sox can use him. Franchise player Rafael Devers, beginning the third year of a $313.5 million extension, may remain at third base while Bregman slides to second, but Breslow says discussions on defensive alignments will be ‘ongoing.’
A lineup hamstrung by unproductive DH Masataka Yoshida and defense-first players like WIlyer Abreu and Ceddane Rafaela suddenly grows longer.
And the very imposing kiddie corps on the way – most notably Kristian Campbell, who may be the second baseman of the future and a roster impact in the present – will benefit from Bregman’s tutelage.
‘There’s great players, veteran players, young players that are ready to get after it and compete,’ says Bregman. ‘From the beginning of this process, ownership has met with us and expressed how they want us to win.
‘They showed us how we have a track record of doing it before. I think everyone here is motivated to win it.’
Says Breslow: ‘It became clearer and clearer Alex was the perfect fit. In Alex, we’re getting an elite defensive infielder. An offensive profile that fits our park almost perfectly.
‘Perhaps most importantly, we’re getting a champion, a winner, a leader, someone who will serve as a mentor to our young, emerging group and will have a lasting impact on our organization.’
And now, it’s almost as if Bregman’s Astros era didn’t exist. Bregman acknowledged it was ‘difficult’ to leave Houston and the respect level he has for the organization and players. And he certainly heard the boos from Fenway fans after the sign-stealing scandal was revealed – a postseason in which Houston eliminated Boston.
‘Yeah. But it’s all good,’ he said, grin only slightly mischievous.
There’s that audacity again – a look that says, ‘Watch me play and 2017 will disappear.’ He needed a home and the Red Sox needed a beacon and suddenly, it’s game on for both of them.
‘You up your game in pressure-packed environments,’ he says. ‘Starting out at LSU was about as much pressure as you can get in college. Being able to play in the playoffs the last eight years in Boston and New York and Philly and Houston yourself – there’s a pressure you put on yourself.
‘It locks you in.’
For at least one year, and perhaps much longer.