Red Sox Legend Reveals Why He Regrets Leaving Boston

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Red Sox Legend Reveals Why He Regrets Leaving Boston originally appeared on NESN. Add NESN as a Preferred Source by clicking here.

It's been 28 years since Mo Vaughn played his last game for the Boston Red Sox, but he still regrets leaving.

Vaughn spent the first eight years of his MLB career with the Red Sox, establishing himself as one of the best hitters in baseball during the 1990s. On top of winning 1995 AL MVP honors, he also made three All-Star teams and won a Silver Slugger with Boston.

Vaughn left in free agency after the 1998 campaign, signing with the Anaheim Angels. He only played four more seasons and steadily declined after leaving the Red Sox, however, watching his OPS decline each season.

In a recent interview with Zach Gelb on WEEI, Vaughn explained why he still regrets leaving Boston.

"Hell yeah, I should've never left!"-Mo Vaughn tells me he regrets leaving the Red Sox and believes he would be in the @baseballhall if he played his entire career in Fenway Park. @WEEIpic.twitter.com/suExja6IgW

— Zach Gelb (@ZachGelb) May 16, 2026

"I should've never left Fenway Park. I would probably be in the Hall of Fame, because I knew that ballpark and that wall like the back of my hand," Vaughn told Gelb. "If I could do it over... Hell yeah, I should've never left... It was awesome."

The 90s version of David Ortiz, Vaughn flourished at Fenway, batting .326/.419/.574 there.

He was on a Hall of Fame path before leaving Boston, slashing .304/.394/.542 with 230 home runs and 752 RBI in his eight years with the Red Sox. He wasn't the same player after leaving Boston, however, never making another All-Star team and compiling just 2.4 WAR with an .838 OPS during his post-Red Sox career.

Many Boston stars struggled after leaving Fenway Park, including Fred Lynn, Nomar Garciaparra and Tony Conigliaro. Perhaps if Vaughn had stayed, he'd have a plaque hanging in Cooperstown right now.

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