FORT MYERS, Fla. — To pull off a move so massive that it would alter the trajectory of the franchise, the Boston Red Sox first had to answer 16 pages worth of questions from agent Scott Boras, Alex Bregman and his wife, Reagan. Then, an ownership group exhausted by half a decade of losing had to summon the energy to pivot after enduring the gut punch of watching Juan Soto slip through its fingers.

For eight solid weeks, chief baseball officer Craig Breslow had to pepper Boras with phone calls, all as Bregman received a flurry of recruiting texts from a Red Sox legend he held in high esteem, Dustin Pedroia.

And when it became clear that signing Bregman would require some creativity and a complicated contract structure, Breslow had to be open to the guidance and expertise of a predecessor, Theo Epstein.

Signing Bregman to a three-year, $120 million deal took three months to play out. At some points, even the club’s top decision-makers placed their percentage chances of landing the star third baseman at single digits. But on Wednesday night, the saga reached its conclusion when manager Alex Cora dozed off while watching a Celtics game, only to wake up to 10 missed calls intended to relay the news.

The Red Sox had pulled off a coup that required top-to-bottom organizational collaboration.

“I honestly just told him the facts,” Pedroia wrote in a text to The Athletic. “I just spoke to him a few times about Boston and my experiences and how great the people are and the city and how great the fans are. How it’s the best place to play and he would be a huge part going forward if that’s what he wanted.”

Bregman, it turns out, wanted it enough to sign despite ambiguity about what position he’ll play. A sign in the Red Sox clubhouse underscored the awkwardness. Both Bregman and the incumbent, Rafael Devers, were listed as being scheduled to work at third base on Monday, the team’s first full-squad workout of the spring. Of course, none of that seemed to matter on Sunday morning, as Bregman settled into his seat during a news conference at JetBlue Park.

“I just want to play wherever it helps the team win,” Bregman said, toeing the company line. “I’ll leave that decision to AC.”

Bregman was flanked by Boras and Breslow, and Cora and CEO Sam Kennedy were seated nearby. The architects of the signing had gathered to mark the beginning of a new chapter, one that was set into motion by a prized free agent raising questions and an organization that proved ready to answer them.

When the Red Sox dispatched officials to California in mid-November for a sit-down with Bregman, the team’s focus had been on another Boras client, Juan Soto.

That fit wasn’t perfect either. The Red Sox were seeking right-handed balance to the lineup and Soto is a left-handed hitter. But Soto is a generational talent, and with the organization committed to spending this winter, the Red Sox felt they had a real chance. The six weeks leading up to the Winter Meetings focused on signing Soto, with the Red Sox mustering a 15-year offer to Soto worth roughly $700 million, sources told The Athletic’s Ken Rosenthal. The offer was complex and competitive.

To help assemble it, Breslow turned to Epstein, who’d been brought in earlier in the year as a senior advisor to Fenway Sports Group.

Soto chose the Mets, which could have been a knock-out blow for an ownership group that in recent years had admittedly been averse to mega contracts. Instead, the group had signaled enough of a chance that Boras came away convinced that principal owner John Henry was once again willing to flex the club’s financial might.

“I think it was after Soto signed (that) we had a discussion,” Boras said. “I could tell from knowing John from back with the Marlins that he had a real onus about, ‘We need to really do things differently from what we have done before.’”

With Soto off the board, the Red Sox turned their focus to Bregman, whose mid-November meeting with the club covered all aspects of the organization. He met with Breslow, Kennedy, Cora and chairman Tom Werner at the Pendry Newport Beach Hotel in Newport Beach, Calif., just a mile from the Boras Corporation headquarters. With help from Boras, Bregman and his wife assembled 16 pages worth of questions.

The free agent wanted to understand the organization’s overall direction, its plans for what the industry considers an elite group of prospects, its commitment to spending and winning, and perhaps most importantly, its plan to bring playoff baseball back to Boston. It’s something Bregman experienced for eight straight seasons in Houston.

“It was unbelievable. He was just going through his checklist of where we see the franchise going,” Kennedy said. “They kind of put us through the wringer. But Bres talked about the future, where we are, where we’re going. And I think that was really, really important for Alex and Reagan to hear.”

The Red Sox quickly demonstrated those plans. Rather than retreat into frustration in the days after losing Soto, Breslow pushed the club’s plans forward, trading two of his top prospects as part of a package to the Chicago White Sox for No. 1 starter Garrett Crochet. With a top pitcher acquired, Breslow shifted his attention back to targeting a right-handed hitter. He explored several options but Bregman remained the priority.

Throughout the winter, Cora was asked often about Bregman’s leadership, defense and pull-side power, a skill set that the manager observed firsthand as a coach in Houston. He knew Bregman would be perfect for Fenway Park. In January, during Fenway Fest, Cora called Bregman a Gold Glove-caliber second baseman. The comments came after Bregman had just won a Gold Glove at third base.

As the Red Sox ramped up their pursuit, the front office elicited the help of one of Bregman’s favorite players and one of Cora’s closest friends, the former Red Sox second baseman Pedroia. A member of two World Series-winning teams in Boston, Pedroia maintained regular contact throughout the winter, reassuring Bregman that he’d fit in Boston. Meanwhile, Breslow kept Red Sox ownership in the loop daily, all while keeping Boras on speed dial.

“(Breslow) told me he had 77 appearances in a season one time, that’s pretty remarkable,” Boras said. “I think he may have led in GM phone calls to me, and it might have been 14 or 15 of them, persistent discussions.”

Those discussions were needed to clear a hurdle. As much as the Red Sox wanted Bregman, a team source confirmed that the club was adamant about not doing a deal for more than four years. The Red Sox wanted flexibility with top infield prospects Kristian Campbell and Marcelo Mayer, two top 30 prospects in baseball, knocking on the door. They’d pay Bregman a high average annual value in a deal deep with deferrals, but the terms had to be shorter than Bregman was seeking from other teams.

As he had done for the pursuit of Soto, Epstein once again emerged as an important voice in the efforts to land Bregman. As an experienced executive who once hired Breslow to join his baseball operations team with the Cubs, Epstein has a steady hand that proved valuable for Boston’s comparatively inexperienced chief baseball officer. Epstein advised Breslow throughout the process.

“Theo was really, really helpful and provided counsel along the way that helped us think about different deal structures and also ripping up different deal structures when they don’t work,” Kennedy said. “I really think it helped Bres in terms of, you’re talking about perhaps the best negotiator in the history of baseball agents, and Bres is still a year and a half, two years on the job.”

While acting as a guiding force, Epstein also made sure to let Breslow have the final call.

“He was incredibly helpful,” Breslow said. “From everything from, ‘Let’s make sure that we zoom out and see and appreciate the big picture’ to here is maybe the right way to communicate. How are we thinking about this or that. Also, he was very respectful of the reality that, ultimately, this had to be my decision. And while his opinion may be something, I needed to do what I felt like I was comfortable with.”

While the Red Sox felt good about their approach, there was still significant uncertainty in the weeks and days leading up to Bregman’s signing. The free agent weighed offers from the Detroit Tigers, Toronto Blue Jays and the Cubs. Internally, the Cubs’ aggressiveness worried the Red Sox the most. Meanwhile, sources told The Athletic’s Rosenthal the Tigers offered Bregman a six-year, $171.5 million contract, well above Boston’s offer.

Still, the Red Sox held their ground.

“There were moments in time where it looked like we were light years away from a deal,” said Breslow, who tried to remember Epstein’s words of wisdom.

Even as the discussions with Bregman continued, the Red Sox explored other options in case the deal fell through.

“I did not think it was going to come together, full stop,” another Red Sox official said. “We were as sort of aggressive as we felt we could be the entire time.”

As Wednesday approached, the negotiations heated up, with Bregman expressing a willingness to leave money and years on the table to sign with Boston. Werner was in England at the time for meetings with Fenway Sports Group’s Liverpool Football Club. But in an effort to push the deal forward, he called Boras at 3:30 a.m.

Later in the day, Cora received word in the late afternoon that talks had progressed. He had just finished the first day of workouts for pitchers and catchers. But by Wednesday night, he still hadn’t heard anything more. He fell asleep to the Celtics game only to awaken at 10:30 p.m. to nearly a dozen missed calls and a text from his daughter, Camila, a senior at Boston College.

“She goes, ‘Let’s fricking go!’ and at first I was like, ‘I hope this text is for me,’” Cora said with a laugh.

Soon, Cora saw a slew of messages from Henry, Breslow and Boras. As the manager was processing the news, Bregman called.

“It became a long night after that,” Cora said.

According to a person involved in the negotiations, the deal was complicated but satisfied Bregman for now. There is $20 million deferred in each year of the deal. He will receive $15 million in salary in 2025, $20 million in 2026 and $20 million in 2027, with player opt outs in ’26-27.

The $20 million deferred will be paid $2 million per year, beginning 10 years from the year it is earned, meaning the $20 million of deferred money from his 2025 salary will be paid in $2 million increments per year from 2035-2044. Bregman also received a $5 million signing bonus. It was a complex deal, but for collective bargaining tax purposes, the Red Sox will be charged $31.7 million per year rather than the $40 million a traditional three-year, $120 million would offer.

Bregman wanted to go to an organization with a chance to win. He became enamored with Boston’s prospect group of Campbell, Mayer and baseball’s No. 1 overall prospect, outfielder Roman Anthony. When Bregman arrived on Sunday, his locker in the JetBlue Park clubhouse had been placed right next to Campbell’s with Mayer and Anthony in the next two spots.

Meanwhile, Boston was attractive for other reasons. Bregman’s wife got accepted to Harvard Extension School early last week, perhaps swaying his decision. She’s entering an entrepreneurial business program that requires her to be on campus for several weeks. She’s also seven months pregnant and due at the end of April.

Where Bregman plays on the field remains an open question. Cora revealed on Sunday that Devers is still building up his throwing program after dealing with soreness in both shoulders last season, an ailment that landed him on the injured list to finish the year.

Though the team has been evasive about nailing down a position, the hard part is over. Bregman is officially a member of the Boston Red Sox.

“My gut is that this guy is going to love Boston,” Kennedy said. “And Boston is going to love him.”

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