CHICAGO — A few years ago at Dodger Stadium, USC quarterback Caleb Williams reintroduced himself to baseball agent Scott Boras. The two had once briefly crossed paths at SoFi Stadium in Los Angeles, but Boras is truly in his element in the VIP area behind home plate, posting up for Dodger games during batting practice and interacting with a mix of clients, team officials and reporters. In this business, there is no off switch.
Boras, the father of three USC graduates, naturally followed the rise of Williams, a Heisman Trophy winner who would become the No. 1 pick in the 2024 NFL Draft. Williams’ father, Carl, who’s heavily involved in the management of his son’s career, also chatted with Boras about the NFL’s machinelike system for elite prospects.
Little did they know that they would intersect again on an epic Chicago sports night, which saw the Bears beat the Green Bay Packers in the playoffs and the Cubs close a five-year, $175 million deal for All-Star third baseman Alex Bregman.
Some 2,000 miles away from Soldier Field, Boras had Da Bears on in the background last Saturday while working from his home office in Southern California. Bregman, a player long coveted by Cubs president of baseball operations Jed Hoyer, was nearing a decision. And it looked like the Packers were on the verge of ending Williams’ magical season.
With Boras having an agency based in Newport Beach, a major-league executive once theorized that he likes to use the time-zone differences to his advantage, trying to catch the other side off guard at an odd hour.
Boras does not view that as a negotiating tactic. Rather, his work ethic was shaped by growing up on a farm outside Sacramento, an environment that required constant attention. As a former minor-league player, he also understands the game’s rhythms and consuming nature.
“There’s an uneasiness when you hold in your hands a player’s career, so you don’t worry about days or time,” Boras said. “Maybe because people know you’re available all the time, they give you information, and then it prompts action. Immediate action.
“That night, we called Jed because we had things that were operational. And he had to make decisions. Otherwise, a different decision was going to happen.”
The Boston Red Sox loomed as a threat to re-sign Bregman, 31, who had opted out of his contract after last season, chasing a third World Series ring and desiring long-term stability for his family at this stage of his career.
As the Bears-Packers game unfolded on a frigid night along Lake Michigan — and Williams eventually began to heat up — how to structure the deferred money became a key point in the Bregman negotiations.
In evaluating the offers, the old farm boy used a metaphor.
“You just have to make sure that you’re getting a little less lipstick and a lot more pig,” Boras said.
Along with Alex Bregman’s on-field production, Jed Hoyer was impressed with the third baseman’s leadership qualities. (Geoff Stellfox / Getty Images)
Inside the Wrigley Field office building, Hoyer ran a Friday staff meeting, sharing his gut feeling that the Bregman deal might go down that weekend and ensuring that everything was in order.
With Fenway Fest on deck that Saturday, the winter event for Red Sox fans and the Boston media could spur some movement. After Bregman waited until February to sign his contract last year, it seemed more likely that he would want a resolution before spring training. And the Cubs felt much better prepared for this moment.
During last season, Hoyer and general manager Carter Hawkins initiated discussions with chairman Tom Ricketts and president of business operations Crane Kenney, hoping to update the club’s philosophy on using deferred money to help finance deals for free agents.
Deferrals were features of the big contracts for Jon Lester and Jason Heyward, who became two members of the unforgettable 2016 World Series team. After breaking a 108-year championship drought, the Cubs seemed to shift toward a more conservative financial outlook.
Deferred money was not made available to Hoyer last year, when the club’s ownership group authorized a four-year, $115 million offer to Bregman.
The frustration within the organization was evident when Bregman chose the Red Sox and a three-year, $120 million deal that included a substantial amount of deferred money and better opt-out flexibility.
In Bregman, the Cubs envisioned the missing piece to their puzzle, an athletic Gold Glove defender and a disciplined right-handed hitter with extensive postseason experience. Bregman also came with a reputation for being an outstanding leader, someone who directed hitters’ meetings, mentored young players and wanted insights into every level of the organization.
Bregman’s intangibles and track record of high-level production checked the boxes from both a traditional scouting standpoint and the model-heavy approach that has taken over Chicago’s front office.
Bregman’s resume and pedigree speak for themselves. He was the No. 2 pick in the 2015 draft out of LSU and a two-time World Series champion with the Houston Astros. Over the years, Hoyer also heard stories about Bregman’s passion and commitment.
In particular, Hoyer listened to A.J. Hinch, the former Astros manager and current Detroit Tigers manager. Hoyer and Hinch once worked together in the San Diego Padres’ front office, an example of how small the baseball world is and how quickly word gets around.
By Friday night, another agent from the Boras Corporation, Scott Chiamparino, alerted Hoyer that another round of the Bregman negotiations was accelerating.
This time, the Cubs were determined to avoid missing a top free-agent target in back-to-back years, which would have felt like another double doink.
Just as the Bears are changing their identity from a team that would lose a playoff game on a field goal attempt that hit the upright and crossbar, the Cubs can still feel the momentum from last year’s playoff run.
“It’s been so great to see the city alive and talking about the Bears,” Hoyer said. “In a lot of ways, it’s kind of inspirational for us, too. We had that this October for a bit. You want to get back to that because the city really does respond when you’re winning.”
Working from his suburban North Shore home, Hoyer went back and forth with Chiamparino over proposals. Boras looped in his analytics team and the Cubs did the same with their group, working toward the numbers that would determine the contract’s net present value and accounting toward the luxury-tax threshold.
With both sides agreeing to $70 million in deferred money, the last element of the negotiations would be finalizing the schedule for those payouts.
“We might have gotten a deal done before kickoff,” Hoyer said, “if it wasn’t for all the spreadsheets.”
To celebrate their next chapter, Bregman and his wife, Reagan, went out to dinner near their home in the Phoenix area. Reagan had already spent part of the day looking at places to live in Chicago. In the restaurant, Bregman certainly noticed the Bears-Packers score when the news began to circulate.
“This could go one of two ways,” Bregman said. “I hope they come back and win.”
Down 21-6, Williams ignited an offense that put up 25 points in the fourth quarter, throwing touchdown passes on two late drives to stun a historic rival and send Bears fans into delirium. After a frenetic 31-27 wild-card victory, Bears coach Ben Johnson screamed inside the postgame locker room: “F——— the Packers!”
Cubs players were also overjoyed. Pete Crow-Armstrong, the All-Star center fielder, was in attendance at Soldier Field when he found out that Bregman would be a new teammate. Immediately after seeing the reports, Gold Glove shortstop Dansby Swanson called Bregman from a friend’s wedding. Cubs pitcher Jameson Taillon, who lives near Bregman in Arizona, also reached out to say congratulations.
“I texted him when the news broke: ‘Dude, let’s freaking go,’” Taillon recalled. “He FaceTimed me. He was like, ‘Hey, we’re just finishing up dinner. Can I come over?’
“I was on the couch, watching the Bears game, about to go to bed. I cleaned up the place and made a margarita.”
Toasting his hard work and good fortune to get to this point, Bregman continued his whirlwind tour with trips to the United Center for Bulls and Blackhawks games, a news conference in the Wrigley Field office building and multiple appearances at Cubs Convention, an annual fan festival at the Sheraton Grand Chicago Riverwalk.
Bregman chose No. 3 to symbolize his pursuit of a third World Series title. As a kid in Albuquerque, he was also drawn to No. 54, the Hall of Fame linebacker from New Mexico who defined a generation of hard-nosed football.
“We were all Brian Urlacher fans,” Bregman said. “Everyone in New Mexico had a Brian Urlacher jersey. My cousins and my family always watched the Bears games. You could tell how the city loves its sports teams. Growing up, WGN was on in our house all the time, so I got to watch a lot of Cubs baseball.”
This particular Cubs team, an especially tight-knit group, just added one of baseball’s best leaders. Of course, Bregman and some of his new teammates are planning to go to Soldier Field for Sunday night’s playoff game against the Los Angeles Rams. The roar of the crowd and the views of the city’s skyline should be inspiring.
“There’s an excitement in the air about Cubs baseball,” Bregman said. “I can’t wait to get after it.”