The TV cameras will be lined up Thursday morning on the second floor of the Wrigley Field office building. Inside a corporate conference room, the Chicago Cubs will introduce Alex Bregman as their new third baseman, and reintroduce themselves as a big-market franchise with serious ambitions to win the World Series.
Shortly after 10:30 a.m., Bregman will put on a No. 3 jersey for the photo op to commemorate the start of his five-year, $175 million contract, a partnership that will be deemed a complete success only if the Cubs stage another championship parade down Lake Shore Drive and Michigan Avenue.
To borrow a quote from John Lackey, one of the former players scheduled to attend this weekend’s 10-year reunion of the 2016 World Series team at Cubs Convention: Bregman didn’t come here for a haircut.
The timing is notable, Bregman agreeing to the deal last Saturday night while more than 31 million viewers on Amazon Prime Video watched the Chicago Bears roar back for their first playoff victory over the Green Bay Packers since World War II.
Two nights later, Bregman got the celebrity treatment in a United Center suite while watching a Chicago Blackhawks game, an outing that drew attention in a city that obsesses over sports the way Washington revolves around politics and Los Angeles draws an identity from Hollywood.
“Everyone is aware that Bregman is something special and different other than his performance,” agent Scott Boras said last month, promoting his client during MLB’s Winter Meetings. “You’re talking about one of the few regular, everyday players that has (nine) consecutive postseason appearances.
“In October, it’s ‘Alex in Wonderland,’ and it’s a ‘Bregularly’ scheduled event, no doubt.”
The playoff resume includes two World Series titles with the Houston Astros, one subsequently tainted by a sign-stealing scandal. Outside of the boos at Yankee Stadium and other road ballparks, Bregman’s reputation didn’t really take a hit because he continued producing at a high level, establishing himself as one of the sport’s foremost clubhouse leaders.
Bregman is fluent in the data and technology that have taken over the game, but he also has a feel for team dynamics, an ability to communicate clearly with teammates and coaches while setting daily expectations.
Some of this probably comes naturally. His father, Sam Bregman, serves as a prosecutor in New Mexico, where he’s running as a Democratic candidate to become the state’s next governor. His late paternal grandfather, Stan Bregman, was a lawyer who once represented the old Washington Senators baseball club. For a sweeping view of the Bregmans’ journey from Eastern Europe toward the American Dream, read this classic Peter Gammons story from The Athletic archives.
Bregman is so driven and competitive that he wore No. 2 with the Astros and Boston Red Sox to remember the slight after the Arizona Diamondbacks passed on him with the top pick in the 2015 draft. Dansby Swanson, the future Cubs shortstop, went No. 1 that year out of Vanderbilt, allowing the Astros to take an undersized LSU infielder with the second pick. One league source described Bregman’s mentality this way: “Every waking hour is about the game, how to win.”
Alex Bregman wears number 2 as a reminder he was picked number 2 in the draft. Now he gets to play alongside Dansby Swanson who was taken
Number 1 that year.— Karl Ravech (@karlravechespn) January 11, 2026
Bregman will wear No. 3 at Wrigley Field, where No. 2 currently belongs to Nico Hoerner, the Gold Glove second baseman and frequent subject of trade rumors. However, the expectation is that they will all work together — Bregman, Hoerner, Swanson and Michael Busch — to form an excellent infield alignment and continue building a culture of baseball gym rats.
Bregman’s home in the Phoenix area should also make him a fixture at the organization’s Arizona complex and a resource for young players who want to learn and get better.
Now the Cubs appear to be acknowledging the mistake they made last February, when their four-year, $115 million offer to Bregman fell short in all of the areas where free agents keep score: years, average annual value, opt-out potential and total guaranteed money.
At that time, Cubs president of baseball operations Jed Hoyer signaled that his front office was not authorized to go beyond a four-year structure, indicating that the organization was also “philosophically” opposed to using deferred money to close the deal.
“Obviously disappointed,” Hoyer said in the immediate aftermath of Bregman choosing the Red Sox. “He’s a great player. He’s a great fit.”
A clubhouse source said that Bregman’s knowledge and experience would have been extremely valuable for a group trying to reach the next level, intangible traits that would also remain durable through slumps and injuries.
“You’re involved in a player, which means you want to get him,” Cubs manager Craig Counsell said during spring training last year. “And when you don’t, you’re disappointed.”
That frustration ultimately gave way to action. Eleven months later, Hoyer extended an even longer offer to a player nearing his 32nd birthday, closing the deal with $70 million in deferred money, according to The Athletic’s Ken Rosenthal. This became the logical next step for a team that won 92 games and a playoff round last year but could not overtake the small-market Milwaukee Brewers.
The last time the Cubs landed a free agent of this magnitude — in terms of commitment, cachet and championship pedigree — Theo Epstein joked that he would have soaked himself in deer urine if that’s what it would’ve taken to sign Jon Lester, an avid hunter who had already earned two World Series rings in Boston.
With Wrigley Field under renovations after the 2014 season, the Cubs held Lester’s news conference at Spiaggia, a since-closed Italian restaurant on the Gold Coast. Lester’s six-year, $155 million contract marked another turning point toward the franchise’s golden age: three consecutive trips to the National League Championship Series, five playoff appearances in six seasons and the end of a 108-year championship drought.
The Cubs don’t obsess over free agents the same way anymore, leaning heavily on model-driven systems to evaluate talent, structure contracts and manage payroll. But Bregman walking into Wrigley Field in the middle of winter is an acknowledgment that not everything can be quantified, and a statement that this team again expects to be playing into late October.