FORT MYERS, Fla. – When Alex Bregman put on a Red Sox jersey for the first time on Sunday morning, it was a full-circle moment and a destination decades in the making.

It began long before Bregman was born into his baseball-loving family. His grandfather, the late Stanley Bregman, was chief legal counsel to the Washington Senators, and as they were known after relocating to Texas in 1972, the Rangers. He signed Ted Williams to be the club’s manager in 1969, and they remained close for the rest of their lives.

“My dad grew up sitting on Ted Williams’ lap,” said Bregman, who happens to have the second-best on-base percentage at Fenway Park of any player in MLB history (minimum 75 plate appearances), behind none other than Williams. “It’s really cool.”

Bregman could’ve started his professional career with the Red Sox. They drafted him out of high school in 2012, but he’d opted to honor his commitment to Louisiana State, and Boston became a "what if" place.

And there was his childhood hero, who helped recruit him, and to whom manager Alex Cora compared him when he described Bregman as a “baseball rat.”

“My favorite player, Dustin Pedroia,” Bregman said with a wide smile. “He reached out to me a few times this offseason and talked to me about how special it was to be a part of the Boston Red Sox.”

Even Bregman’s wildest experience at Fenway was a full circle. Just not his own.

“When (Rafael) Devers hit an inside-the-parker in 2017 against us in the playoffs,” he recalled. “I felt like I’ve never seen a crowd that crazy in my life.”

The cost of winning

Bregman is the clearest sign thus far that the Red Sox are completing a circle of their own, getting back to being the type of franchise that prioritizes winning. Even after its significant salary deferrals, the three-year, $120 million contract puts the club over the first luxury tax threshold ($241 million) for the first time since 2022. They could find ways to get under the threshold before the midseason trade deadline, but that’s unlikely to happen if the season is going well. If they’re the contenders they hope to be this year, they’ll likely take on salary before the deadline, and end up paying the 20% tax on the overage. They’ll also incur increasing penalties for every consecutive season over the threshold.

Boston also forfeited a draft pick to the Astros, the cost of signing a free agent who received a qualifying offer. (That, however, is something of a zero-sum game, as the Padres have to send the Red Sox a pick for signing Nick Pivetta.)

For several years, the Red Sox avoided paying either type of price almost entirely. But they were willing to pay both for Bregman.

Onus on ownership

Bregman’s agent, Scott Boras, has dealt with the Red Sox for decades, representing everyone from current chief baseball officer Craig Breslow and Jason Varitek, to JD Martinez, Xander Bogaerts, and Masataka Yoshida. He’s also known for criticizing wealthy teams that don’t spend, and the Red Sox, who consistently rank No. 3 in Forbes’ annual MLB team valuations, have qualified as such in recent years.

When the offseason began, Boras and his client saw a different version of the Red Sox almost immediately; they were in constant contact, aggressive, and urgent.

They were acting like The Red Sox again.

“From the beginning of this process, ownership has met with us and expressed how they want to win,” Bregman said. “When Scott and I started out and we started talking about places we may want to go, winning was the most important. So when they showed their vision of how this organization is going to win now and in the future, that was pretty cool.”

It was particularly evident at the ownership level. John Henry, the club’s principal owner, has drawn near-constant criticism over the last half-decade for his perceived tightfistedness and disinterest in the team, especially compared to more recent additions to the Fenway Sports Group portfolio. A conversation with him really moved the needle for the agent.

“I could tell from knowing John (when he owned) the Marlins and such that he had a real onus about, ‘We need to really do things differently than what we’ve done before,’” said Boras. “So I knew from the ownership level that they were really looking to correct what has happened the last five, six years.”

The right fix

The Red Sox went into the offseason seeking a right-handed hitter to balance out the lineup. In Bregman, they’re getting so much more.

“We’re getting an elite defensive infielder. We’re getting an offensive profile that fits our park almost perfectly,” Breslow explained. “And perhaps most importantly, we’re getting a champion, a winner, a leader, someone who will serve as a mentor to our emerging young group, and someone who will have a lasting impact on this organization.”

“He fits like a glove for our organization,” agreed team president Sam Kennedy.

The Red Sox still haven’t announced exactly how the infield will be configured now that the longtime third baseman is part of the equation. In the coming weeks he’ll put in work there, as well as second and shortstop, but the team is confident he makes them better in several tangible and intangible ways, regardless.

“In 24 hours he has impacted the organization already,” said Cora, who was Bregman’s bench coach on the '17 Astros. “One thing he’s gonna do, he’s gonna challenge everybody here. I know that. He’s gonna challenge you. He’s gonna ask about pitch usage, about swing decisions, about scouting reporters, the nutrition side of it.

“He will do that — not in a bad way, he wants to learn, he wants to be involved, and that’s very important. And I think in 24 hours, his teammates, the coaching staff, the front office has seen (why) I’ve been talking about him for a long period of time.”

Welcome to the Red Sox renaissance

Bregman chose Boston, and in doing so, told the world he believes the Red Sox are on the brink of resurgence. Even more so because he left longer-term offers with more guaranteed money on the table.

Getting his new team to the finish line was the first thing he mentioned in his opening remarks. He played in each of the last eight postseasons, tied for the longest active streak in the game, and has no intention of breaking it now.

“I’ve been fortunate to be in the playoffs the first eight years of my career, and I plan on continuing to do that here,” Bregman said. “I’m a winning player. It’s a winning organization. Those players are winning players, we have winning coaches here.

“I plan on winning here.”

Not just winning. Winning in one of the most intense and passionate sports markets in the world.

“Pressure is a privilege,” Bregman said. “You kind of up your game.”

The Red Sox already have.

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