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Cubs 2-Time All-Star Sends Alex Bregman Message After Red Sox Exit

Forbes Published Jul 2, 2026 Reviewed Jul 3, 2026 ✓ Reviewed by citations.press editors
Citation-ready fact
Alex Bregman, signed by the Chicago Cubs for $175 million in the offseason, hit .181 in June with a .253 slugging percentage and chased pitches outside the zone at a 24% rate—the highest of his career over a full season.
0.181 · Alex Bregman's June batting average0.253 · Alex Bregman's June slugging percentage24 % · Alex Bregman's chase rate outside the zone in June
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Citation-ready fact
Two-time Cubs All-Star and World Series champion Jon Lester, who transitioned from the Boston Red Sox to the Cubs, stated that his own first month with the Cubs was among the longest he experienced in the majors and that he “wanted the season total numbers in April,” indicating early-season pressure.
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Citation-ready fact
Jon Lester, a former pitcher for the Red Sox and Cubs, observed that Alex Bregman “may be banged up a little bit” and is likely “pressing” under the pressure of his $175 million contract and high expectations to hit .270 to .290 with 25 to 30 home runs.
175000000 USD · Alex Bregman's contract valueat least 25 · Alex Bregman's expected home run totalat least 30 · Alex Bregman's expected home run totalat least 0.27 · Alex Bregman's expected batting average floorat least 0.29 · Alex Bregman's expected batting average ceiling
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The Chicago Cubs are struggling and losing ground in the NL Central, with star offseason acquisition Alex Bregman facing intense scrutiny. Bregman, signed for $175 million, is mired in a significant slump, hitting just .181 in June with concerning chase rates. Former Cubs World Series champion Jon Lester, who also transitioned from the Red Sox, offered insight into Bregman's difficulties. Lester recalled his own challenging first month with the Cubs, suggesting Bregman is likely "pressing" under the immense pressure of his new contract and high expectations. He also hinted at a possible injury, noting Bregman "may be banged up a little bit." Lester expressed hope that Bregman can overcome this period and regain his All-Star form, drawing a parallel to his own successful turnaround with the Cubs.

The Chicago Cubs have seen the distance in the National League Central division grow as their impressive start to the season has devolved into some struggles and injuries for several key players.

And as the team looks to reclaim its playoff momentum, the spotlight has settled on former Boston Red Sox star Alex Bregman, who joined the Cubs on a blockbuster $175 million deal in the offseason.

“Bregman has been mired in a season long slump that has only gotten worse in June,” ESPN’s Jesse Rogers wrote this week. “Before Monday's win, he was hitting .181 (in June) with a .253 slugging percentage. He was also chasing pitches outside the zone at a 24% rate, which would be the highest of his career over a full season.

Bregman has been a consistent presence at the plate for the Red Sox as well as the Houston Astros in his career, so the slump is fairly surprising. But one of the few individuals who can really relate to what Bregman is going through this season sent a message on the issues based on his own former struggles with the Cubs.

“That first month was probably one of the longest months I’ve ever had in the big leagues. I wanted the season total numbers in April,” two-time Cubs All-Star and World Series champion pitcher Jon Lester said of his own transition from the Red Sox to Cubs, during a recent episode of “North Side Territory.” “You lose sight sometimes of who you are and what you’ve done and the track record and that sort of thing. So, I think for Bregman… I think he might just be pressing a little bit and you know wanting to be Bregman, wanting to hit that .270 to .290 with 25 to 30 homers… He wants to hit the four home runs before his first at bat.”

Few players understand the pressure that comes with leaving Boston for another high-profile destination — or vice versa — better than Lester. After helping Boston win two World Series titles, Lester joined the Cubs and became a cornerstone of Chicago’s historic championship run in 2016.

For the former pitcher, the pressure of a big free agent contract resulted in some poor performances to start his Cubs tenure. And that could be the case for Bregman as well, though Lester was quick to note there might be another explanation.

“He may be banged up a little bit, we don’t know that,” Lester added. “But I know he’s definitely out there grinding and he’s definitely out there giving it everything he has… But hopefully he can kind of hold on in where he’s at right now and maybe get hot here in the next month or so and be Bregman like numbers toward the end of the season.”

Cubs fans can certainly hope that Bregman’s tenure with the team charts a similar path to that of Lester’s after he signed following his own successful Red Sox stint.

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