The Red Sox suffered another loss on Monday. But this one hurt more than the others.

Beloved color analyst Dennis Eckersley announced that he is departing the booth at the season’s end, according to NESN.

After 50 years in baseball, Eckersley told the Boston Globe's Chad Finn that he plans to spend more time with family in California.

The Sox great also has deep ties to the Bay Area after winning a Cy Young Award and a World Series with the Oakland Athletics, for whom he also made numerous All-Star appearances. He was enshrined into the Baseball Hall of Fame wearing an A’s cap in 2004, according to NESN.

But it was in Boston where Eckersley found new life as a broadcaster for NESN. At first filling in for the late Jerry Remy, Eckersley quickly became ingrained in the team’s culture, and known for his humor and quirky baseball terminology.

Eckersley’s Hall of Fame playing career is one of the more remarkable in the modern era.

After earning trips to the All-Star Game as a starting pitcher for the Red Sox and Cleveland Indians, Eckersley’s career stalled as he sought treatment for alcoholism following an underwhelming stint with the Chicago Cubs, according to the Chigaco Tribune. This led to a triumphant return and second act as a reliever, which saw The Eck emerge as the game’s most feared closer. In 1992, Eckersley saved a career-best 51 games en route to winning the American League MVP, the paper stated.

In 1998, Eckersley returned to Boston for one final season with the Red Sox before retiring, with 197 career wins and 390 career saves, according to Baseball Reference.com. But this stopover led to Act Three – joining NESN as an analyst in 2003.

If the story of a Sox reliever overcoming personal demons, switching careers, and becoming a Boston fixture seems familiar, it should. It greatly mirrors that of “Cheers” protagonist Sam Malone. The similarity appears to be just that, however, as Ted Danson’s iconic character debuted in 1982, Eckersley (then in his first Boston go-around) made the All-Star Game for the Red Sox as a starting pitcher that same year.

Boston Celtics Who Went Hollywood

Celtics legends who starred in film and television.

30 Celebrities That are Red Sox Fans

There are many celebrities that are a part of the Red Sox Nation! Some have season tickets while you may see some at only a couple of games every year.

More From WSHK-WSAK 102.1 & 105.3 The Shark