1 Jon Lester reminder says everything about Alex Bregman's Cubs tenure

When Alex Bregman signed his five-year, $175 million contract with the Chicago Cubs, it felt like the beginning of a new era. Jed Hoyer and Tom Ricketts finally inked a modern baseball deal, with deferrals and an AAV that began firmly in the $30 million range, to get a player who would slot into the middle of the lineup while also acting as a leader in the clubhouse. Alas, he has not come close to living up to that agreement so far.

His disappointing performance was also paired with a noticeable incident in which he failed to hustle to beat out a grounder at first against the Brewers and, instead of just saying he regretted not running harder, caveated the admission by mentioning the soft tissue injuries he's dealt with. Needless to say, not a good look. The only clear positive on the field has been his defense.

With all of that said, this is only just over three months into year one of the deal. Bregman has a track record and has built a reputation as a good teammate and hard worker, even if some of that hasn't necessarily shone through. Moreover, he's not the first big-name player to struggle in Chicago after signing a deal out of Boston.

Jon Lester recently appeared on the North Side Territory podcast with Sahadev Sharma and Patrick Mooney and shared his thoughts on Bregman from the perspective of someone who has been in his position. Everyone looks back at Lester's Cubs tenure fondly, but his six-year, $155 million deal got off to a similarly rocky start when he posted a 6.23 ERA through March and April.

By the end of his season, though, he sported a pristine 3.34 ERA across 205 innings. The situations aren't one-to-one between a position player and a pitcher, and Lester can't read Bregman's mind, but he understands the pressure to perform on a big contract and the desire for "the season total numbers in April."

Another good point Lester made is that it's not as if Bregman's performance has been completely disastrous. A 96 wRC+ is just a few points from league average, even if the slug has been down. If he can hold around that spot and put together a hot month or two at some point, that alone would likely be enough to make his season line look more Bregman-esque. After all, Lester's own Cubs debut season was full of ups and downs to get to that final 3.34 mark. He had three entire months where his ERA was north of 5.00, but he made up for it because every other month, he was lights-out.

There are signs Alex Bregman could still salvage his 2026 season

The important thing for Bregman, in Lester's eyes, is to avoid pressing too hard and get back to that approach of focusing on helping the team one day at a time. There are at least some reasons to be encouraged about the rest of his season. While his bat speed has dropped considerably to 69.9 MPH and his overall quality of contact has dropped across the board, he is still great at squaring up the ball, managing a 31.6 percent squared-up rate. His plate discipline is also still great, with a 93rd percentile chase rate and 85th percentile whiff rate.

The point is, there are examples of veterans in Cubs uniforms who have looked middling to downright awful for lengthy stretches of time (a la Dansby Swanson) and still ended their seasons right in line with their careers. Bregman is earning his mediocre numbers, but so were Swanson and Lester during their brutal slumps. I'm not saying it will happen, but there is a possibility that this middling beginning of the third baseman's career in Chicago will be just a blip.

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