Alex Bregman Could Bog Down Free Agency with Huge Contract Ask
Alex Bregman is one of the top three position players on the market behind Juan Soto and right there with Willy Adames in most estimations. Estimates from MLB Trade Rumors, ESPN’s Kiley McDaniel, and The Athletic’s Tim Britton all have the third baseman — who could move to second or short depending on the situation — all have him at six or seven years at $182-189 million. That’s a lot for a guy entering his age-31 season, but the general sense has been that he’ll target Matt Chapman‘s six-year, $151 million extension with the Giants as a baseline.
Considering he’s nearly a year younger, Bregman should be able to get at least as much as his fellow Scott Boras client. However, the path to get there might be similar to what Chapman and Cody Bellinger, another member of Team Boras, had to follow. Ken Rosenthal suspects Bregman and Boras might actually be targeting the 11-year, $350 million extension Manny Machado inked with the Padres prior to his age-30 season in 2023.
More power to Bregman if he’s willing to let his agent take that demand to teams, but it seems like a recipe for waiting until camps open and then taking a short-term deal with opt-outs. That worked out very well for Chapman, who settled for a three-year, $54 million deal with San Francisco that had opt-outs after the ’24 and ’25 seasons. While he played well enough to get the extension, things didn’t work out quite the same on the North Side.
Bellinger’s market never materialized last offseason, in large part due to Boras overvaluing a market that featured a huge vacuum behind Shohei Ohtani. I still maintain that the Cubs thought he’d play well enough to make opting out of the remaining $52.5 million a no-brainer, thus giving them more available payroll space and roster flexibility than they have now. I also maintain that Bellinger could have gotten more than that this year, not to mention the ability to choose his next destination, but alas.
Even though Soto’s courtship probably won’t be as much of a farce as what we saw with Ohtani, who had no intention of signing with anyone other than the Dodgers, it’ll be narrow by nature. Suitors for Bregman and Adames should be far more plentiful, which could make their decisions more pivotal to the market’s development. Assuming the CAA-repped Adames is dealing with more realistic expectations, Bregman could be left on an island waiting for rescuers to come along at the last minute.
As for how this impacts the Cubs, well, that remains to be seen. They figure to be active on the trade scene, whether it’s with prospects, veterans, or both, and the two players other than Bellinger who are mentioned most often are Nico Hoerner and Isaac Paredes. Neither provides a direct comp to Bregman in terms of output, but there’s plenty of positional overlap and both are waaaaay cheaper from a salary perspective.
Whether it’s a team that misses out on Bregman — or Adames, for that matter — or one that is tired of waiting and isn’t going to entertain a deal of more than seven years or $150 million, Jed Hoyer could find his phone ringing more than usual. Then again, would he really be trying to retool the roster in such a big way at the last minute should Bregman’s courtship indeed drag out? Too many hypotheticals involved to say anything definitively.
It seems to me that Boras has lost his fastball and has now become a junkballer who falls behind in the count more often than is productive. He’s always clogged up the market with his bevy of players, it’s just that now they seem to be waiting on monster deals that were simply never there. Maybe I’m wrong and Bregman gets the bag this winter before teams start reporting to spring training, but I just can’t imagine he’s going to end up getting anything close to the Machado deal.
I hope I’m also wrong about the speed and development of this year’s free agent market, because this is boring AF and I desperately need something to take my mind off the Bears.