Stunning Details Prove How Desperate Cubs Were to Sign Alex Bregman
Hey, when you’re wrong, you’re wrong and boy was I ever. Relatively speaking, I have defended the majority of Jed Hoyer’s moves since he took over for Theo Epstein, but it’s been a decade since the Chicago Cubs truly outbid everyone else for their No. 1 target in free agency. We love to engage with rumors on a daily basis, you guys love to eat that up as well, but let’s be real here, the Cubs have had a crush on Alex Bregman since last year and this time around they made sure to sign their guy.
Sure, the Cubs were looking at Bo Bichette and recently a Cody Bellinger reunion was gaining momentum, but Bregman has been on their radar since Hoyer had to convince Tom Ricketts a year ago to spend a little more. That pursuit culminated in the Cubs offering Bregman a four-year contract worth $115 million. That was a $28.75 million AAV for the third baseman, who turned it down in favor of a three-year, $120 million deal from the Boston Red Sox.
Sure, on the surface it seemed like a no-brainer for Bregman to take what looks like $40 million a year from the Red Sox, but that deal included massive deferrals and most importantly opt outs that allowed Bregman to re-enter the free agent market this offseason.
The Cubs didn’t increase their offer to Bregman heading into the 2025 season, but now Hoyer proved the haters wrong. The organization changed course. They changed their philosophy. They did what teams have to sometimes do, get desperate.
Cubs Out-Bid Red Sox for Bregman
This was probably at the limit of Hoyer’s comfort zone, but how often have you seen him aggressively go after free agents on the other side of 30-years-old with huge contracts? Bregman will be in his age-32 season this year and not only did the Cubs offer him more overall money, more years, a higher AAV, they out-bid the Red Sox for him.
The Cubs signed Bregman to a five-year deal worth $175 million. That’s an average annual value of $35 million, $6.25 million more per year than their offer from 2025. According to MassLive.com, the Red Sox also offered Bregman five years, but stopped their bidding at $165 million.
On paper, the $2 million difference per year may not seem like a big deal, but there are a couple more factors that prove how badly the Cubs wanted Bregman.
A quick reminder from last year’s Bregman pursuit by the Cubs. According to Bruce Levine the Cubs had no intention of giving big free agents any deferred money in long-term contracts. That included Bregman, who obviously turned down the Cubs in favor of the Red Sox last season in large part because of deferred money.
It’s for that reason alone that I as well as many Cubs fans felt the team had no chance in signing Bregman this offseason. He’s a year older, coming off an injury, so why would they change their mind now when it comes to deferrals? I mean, the Cubs didn’t even consider it for Shohei Ohtani.
Well, not only did the Cubs change their mind on the whole deferred money thing, this deal with Bregman has a huge chunk of deferred money.
The Athletic’s Ken Rosenthal reported on Sunday that out of Bregman’s $175 million guaranteed contract, $70 will come in deferred payments by the Cubs.
So, the Cubs offered Bregman more money, decided to include deferred money, but you may be asking yourself why didn’t the Red Sox do the same thing they did a year ago? Well, according to MassLive.com, the Red Sox were willing to do include deferred money to bring back Bregman, but the Cubs’ structure was simply better.
And here’s the detail that continues to make the Cubs a top destination for star players in free agency. Despite the criticism the team receives, the Cubs made the Red Sox look like a joke.
Yes, money may have been the difference, but pro athletes are people too. They have the same issues as you and I. Alex Bregman wanted stability, loyalty and the Cubs offered it to him when the Red Sox wouldn’t.
Via MassLive.com.
Obviously, the Cubs offering more money on an annual basis was a huge factor. In the end, too, multiple other factors made Chicago’s offer more attractive.
But Boston’s unwillingness to include a full no-trade clause like the Cubs did proved to be a sticking point as well. So did, according to sources, how the Red Sox planned to schedule out payments of the significant amount of deferred money in their offer.
Bregman has two young children and finding a permanent baseball home was hugely important to him as he didn’t want his family life further disrupted now that he’ll be playing this season in his third different city of the last three years. The Red Sox wouldn’t bend on their refusal to grant a full no-trade clause, citing organizational policy.
Further, while a good chunk of the Cubs’ bid (reportedly $70 million) was also deferred, the Red Sox’ offer involved payments stretching out decades, further subtracting from the actual value of the deal.
The Cubs acted like the big-market team that they are. They out-bid another team. Maybe you think it’s a bad contract or maybe you preferred a different player, but this is exactly how Cubs fans want the Cubs to act.
No half measures. Go big. Go Cubs.