Jon Lester: Red Sox are ‘too smart’ to be long-term cellar dwellers

"I’m sure Bres is in a tough spot," former Red Sox southpaw Jon Lester said.

Jon Lester won two World Series with the Red Sox in 2007 and 2013. (Photo by Jamie Squire/Getty Images)

February 4, 2024

2 minutes to read

The last few years haven’t been particularly kind to Red Sox fans.

Despite winning four World Series titles over the past 20 years, Boston has finished in last place of the AL East in three out of the last four seasons.

And with the Red Sox in the midst of another underwhelming offseason, there isn’t a lot of optimism regarding Boston’s chances of clawing its way up the standings in 2024.

The chances of another bleak summer in Boston is not lost on former Sox southpaw Jon Lester, who won World Series titles with the Red Sox in 2007 and 2013.

In an interview with USA Today’s Bob Nightengale, Lester acknowledged that his former teammate and new Red Sox chief baseball officer Craig Breslow is currently in a “tough spot,” especially with Boston expected to operate at a lower payroll than its 2023 numbers.

However, Lester added that he doesn’t think Boston’s recent status as an AL East cellar-dweller will continue in the coming years.

“It’s tough being the new guy coming in,” Lester told Nightengale. “I’m sure Bres is in a tough spot. I’m sure it will take awhile for him to get his feet under him. But we all know the Red Sox won’t be down for long. They’re too smart over there.”

While it’s tough to ignore the lack of impact offseason moves reeled off by Boston over the last few months, Lester’s comments likely involve around the addition of both Breslow and former Sox GM Theo Epstein, who is joining the Fenway Sports Group and will serve as a senior advisor.

Breslow, a Yale graduate who was dubbed “the smartest man in baseball” by Minneapolis Star-Tribune writer LaVelle E. Neal III, played a key role in overhauling the Cubs’ pitching development staff during his time as an assistant GM and director of the team’s pitching department.

Boston has already significantly overhauled its pitching personnel within the organization. Along with appointing former Sox reliever Andrew Bailey as the team’s new pitching coach, the Red Sox added Justin Willard as the team’s director of pitching and hired Driveline founder Kyle Boddy as a pitching advisor.

Still, with spring training just a few weeks away, the Red Sox still have several holes that they need to address if Boston has any hopes of avoiding another last-place finish this fall.