FORT MYERS, Fla. — In a transformative move poised to reshape the Boston Red Sox franchise, the team first tackled a comprehensive 16-page questionnaire from agent Scott Boras, as well as queries from star player Alex Bregman and his wife, Reagan. The ownership group, weary from several years of underperformance, needed a renewed sense of purpose, especially after witnessing Juan Soto’s departure to another team.

For eight weeks, Craig Breslow, the chief baseball officer, maintained an ongoing dialogue with Boras, while Bregman received numerous persuasive messages from beloved Red Sox icon Dustin Pedroia, whom he admired greatly.

As negotiations revealed the complexities of securing a deal for Bregman, Breslow was encouraged to seek strategic insights from the former Red Sox executive, Theo Epstein, to navigate the process effectively.

Ultimately, it took three months and a hefty three-year, $120 million contract to bring Bregman into the fold. During the lengthy negotiations, the team’s leadership often estimated their chances of success to be in the single digits. However, on Wednesday evening, the story culminated in an unexpected moment for manager Alex Cora, who dozed off while watching a Celtics game, only to awaken to a barrage of missed calls that conveyed the momentous news.

The Red Sox had executed a remarkable organizational endeavor.

“I simply laid out the facts to him,” Pedroia shared in a message to The Athletic. “I described what Boston means to me, recounting my experiences and emphasizing the exceptional nature of the fans and the city. I communicated how significant a role he would play moving forward if he chose to join us.”

It turns out Bregman was eager to make the leap, even with uncertainties surrounding his position on the field. The situation became clear during practice, where both Bregman and the current third baseman, Rafael Devers, were scheduled to train at third base during the team’s initial full-squad session of spring. However, that context faded into the background on Sunday morning, as Bregman took the stage at a press conference at JetBlue Park.

“I’m willing to play wherever it contributes to the team’s success,” Bregman stated, aligning himself with the organization’s goals. “I’ll leave those decisions to AC.”

Bregman was joined by Boras and Breslow, while Cora and CEO Sam Kennedy were also present, signifying the collective effort behind this significant acquisition.

Initially, when the Red Sox dispatched representatives to California in mid-November, their sights were set on another Boras client, Juan Soto.

While Soto was undeniably talented, he didn’t fully meet the team’s needs, as they were looking for more right-handed hitters. Despite being a generational player, Soto’s left-handed bat didn’t align perfectly with the Red Sox roster. Nevertheless, the organization was committed to investing during this offseason, viewing themselves as contenders for Soto’s services. In the weeks leading up to the Winter Meetings, the team pursued Soto vigorously, reportedly offering a complicated 15-year deal worth around $700 million, as reported by The Athletic’s Ken Rosenthal. This offer was ambitious and competitive.

Epstein, who was introduced earlier that year as a senior advisor to Fenway Sports Group, lent his expertise during this critical period.

When Soto chose to join the Mets, the setback could have severely impacted a management group that had, in recent years, shied away from large contracts. However, Boras left with the impression that principal owner John Henry was prepared to reinstate the club’s financial clout.

After Juan Soto, left, signed with the Mets, agent Scott Boras noted Boston’s ambition to recruit a top-tier free agent. (Al Bello / Getty Images)

Boras remarked, “After Soto’s decision, we had a conversation. I sensed John, having worked with him previously at the Marlins, was genuinely eager to approach things differently this time.”

Shifting focus to Bregman, the Red Sox approached him mid-November with a thorough outline of the organization’s ambitions. His meeting with Breslow, Kennedy, Cora, and chairman Tom Werner took place at the Pendry Newport Beach Hotel in Newport Beach, California, near Boras Corporation headquarters. With Boras’s help, Bregman and Reagan prepared an extensive list of 16 questions.

Bregman sought clarity regarding the organization’s strategic direction, its plans concerning some impressive prospects, the commitment to competitive spending, and importantly, the strategy for returning playoff baseball to Boston—a tradition he had enjoyed during his tenure in Houston.

“It was an incredible experience; he was very thorough in evaluating our vision,” Kennedy recounted. “They really put us to the test. Breslow articulated our future strategy, which was crucial for Alex and Reagan to comprehend.”

Following Soto’s departure, the Red Sox rallied quickly, trading two top prospects to the Chicago White Sox to acquire ace pitcher Garrett Crochet. With their rotation fortified, Breslow narrowed his focus back to solidifying the lineup with a right-handed bat, maintaining Bregman as the top priority.

Cora often discussed Bregman’s leadership qualities and defensive prowess throughout the winter, citing his impressive skillset honed during their time in Houston. Cora anticipated Bregman’s fit within Fenway Park as advantageous. During Fenway Fest in January, Cora praised Bregman, referring to him as a potential Gold Glove-caliber player.

To fortify their position, the Red Sox involved Pedroia, one of Bregman’s idols and a member of two World Series-winning squads. Pedroia consistently communicated with Bregman throughout the winter, assuring him of a seamless transition to Boston. Meanwhile, Breslow kept Red Sox ownership informed at every step, remaining in close contact with Boras.

Boras noted that Breslow was remarkably persistent, engaging in numerous discussions—at least 14 or 15 calls during the negotiating process.

A crucial point in discussions arose as the Red Sox desired to keep Bregman’s contract below a four-year term, aiming for flexibility with emerging infield prospects Kristian Campbell and Marcelo Mayer. They proposed a lucrative annual deal with considerable deferrals while keeping the overall term shorter than other interested teams’ offers.

As he had done with Soto, Epstein played another pivotal role in the pursuit of Bregman, leveraging his extensive negotiation experience to aid Breslow. By guiding Breslow in considering various deal frameworks, he ensured the team was prepared to pivot when necessary.

“Theo’s insights were invaluable, helping us strategize multiple deal structures and navigate adjustments,” Kennedy elaborated. “It was particularly beneficial for Breslow to have someone of Theo’s caliber in his corner.”

Even as Epstein provided strategic guidance, he respected Breslow’s autonomy in decision-making.

“Theo was incredibly supportive,” Breslow confirmed. “He helped us maintain a broad perspective while ensuring I felt empowered to make the calls that aligned with my comfort level.”

Despite confidence in their strategies, uncertainty lingered in the days leading up to Bregman’s signing. The free agent was considering offers from teams like the Detroit Tigers, Toronto Blue Jays, and the Cubs. The Cubs’ aggressive push was a concern for the Red Sox. Reports indicated that Detroit had extended a hefty six-year, $171.5 million offer to Bregman, far exceeding Boston’s proposal.

Nonetheless, the Red Sox stood firm in their approach.

“At times, it felt like an agreement was out of reach,” admitted Breslow, as he recalled Ezra Epstein’s thoughtful guidance during difficulties.

Even as negotiations progressed with Bregman, the Red Sox kept exploring backup options, preparing for the possibility of failure.

“I wasn’t convinced we were close to finalizing anything,” voiced another Red Sox official. “We were as proactive as we could be throughout the entire process.”

Alex Cora, left, and Alex Bregman shares a history from their time with the Houston Astros. (Maddie Malhotra / Boston Red Sox / Getty Images)

As Wednesday approached, the stakes heightened, with Bregman indicating a willingness to prioritize signing with Boston over financial gain. During this time, Werner was in England for meetings with Liverpool Football Club under Fenway Sports Group’s auspices. In a bid to expedite negotiations, he reached out to Boras at an unearthly hour—3:30 a.m.

Later that day, Cora heard promising updates regarding the negotiation’s progress, right after completing the initial pitcher and catcher workouts. Yet, as night fell, he remained in the dark. As he dozed off watching the Celtics play, he suddenly awoke at 10:30 p.m. to find nearly a dozen missed calls and a message from his daughter, Camila, a senior at Boston College.

“She texted, ‘Let’s fricking go!’ My first thought was, ‘I hope this is for me,’” Cora recounted with humor.

Shortly after, Cora discovered several messages from Henry, Breslow, and Boras. Just as he processed the flood of information, Bregman called him.

“It was a long night after that,” Cora reminisced.

According to involved sources, the deal was intricate yet ultimately met Bregman’s demands for now. It includes $20 million in deferrals each year. His salary will be structured at $15 million for 2025, $20 million for 2026, and another $20 million for 2027, with player opt-out options in the latter two years. Notably, the deferred payments will commence ten years post-earnings, disbursed over subsequent years. Bregman also secured a signing bonus of $5 million. Despite the proposal’s complexity, it allows the Red Sox to record a cap figure of $31.7 million annually, rather than the $40 million figure of a standard three-year, $120 million agreement.

Bregman was drawn to a franchise with a real chance at contention. He showed enthusiasm towards Boston’s talented prospect pool, including top-tier talents Campbell, Mayer, and elite outfielder Roman Anthony. Upon his arrival on Sunday, he discovered his locker conveniently located next to Campbell’s, with Mayer and Anthony next in line.

Boston had additional appeals beyond baseball. Just last week, Bregman’s wife got accepted into Harvard Extension School’s entrepreneurial program, which might have influenced her decision-making. She is presently seven months pregnant and due in late April, requiring her proximity to campus.

The specifics of Bregman’s on-field role remain to be clarified. Cora noted on Sunday that Devers is still rehabilitating his throwing arm after a shoulder injury that hindered his previous season. While the team has been circumspect about defining Bregman’s position, what remains clear is that Bregman is officially a cherished member of the Boston Red Sox.

“My intuition tells me this athlete is going to thrive in Boston,” Kennedy remarked. “And Boston will undoubtedly embrace him.”

(Main photo of Bregman: Maddie Malhotra / Boston Red Sox / Getty Images)