Run into Dennis Eckersley in the press box or media elevator at Fenway Park and chances are, he’s going to ask you a question.

He’s a Hall of Famer, MVP, Cy Young winner and World Series champion who spent 24 seasons in the big leagues and 20 more in the broadcast booth – you’d think there wouldn’t be a baseball question Eckersley didn’t already know the answer to.

But he’s always hungry for more. More information, more knowledge, deeper wisdom, another perspective. He’s a master at never pretending to know it all.

It’s his humility that was among the many reasons he became an Emmy Award winning broadcaster, and why millions of Red Sox fans across the country were surely saddened on Monday, when Eckersley announced that he’d be retiring from his broadcasting career at the end of the 2022 season.

“After 50 years in Major League Baseball, I am excited about this next chapter of my life,” said Eckersley. “I will continue to be an ambassador for the club and a proud member of Red Sox Nation, while transitioning to life after baseball alongside my wife Jennifer, my children and my grandchildren.

“I’m forever grateful to NESN, the Red Sox, my family and the fans for supporting me throughout my career and through this decision and I look forward to remaining engaged with the team in a variety of capacities for years to come.”

It was 50 years ago that Eckersley was Cleveland’s third-round draft pick as a 17-year-old out of Washington High School in Fremont, California.

He quickly became a sensation with Cleveland, but was traded to the Red Sox in 1978 after his first wife, Denise, left him for his teammate and best friend, Rick Manning. The devastation fueled his success in Boston, where he was among the game’s best starting pitchers until he was traded to the Cubs in 1984.

Three seasons of playing day games for the Cubs in Chicago and enjoying the nightlife a little too much led Eckersley to realize he had a drinking problem, which he’s discussed openly throughout his life. And after sobering up in the ’86 offseason and getting traded to the Oakland A’s, Hall of Fame Manager Tony La Russa moved him to the bullpen and one of the game’s best-ever closers was born.

But for all the success Eckersley had in Oakland, where he won the American League Championship Series MVP and World Series in ‘89, put together one of the best relief seasons ever in ‘90, and won the A.L. MVP and Cy Young in ‘92, he often remembers his failures as being just as impactful.

There was the Kirk Gibson home run in the ‘88 World Series, when Eckersley was one out away from closing out a Game 1 victory against the Dodgers but Gibson, playing on two bad legs, clobbered a regrettable backdoor slider for a walkoff home run.

And the 1992 ALCS, when Eckersley served up a tying, two-run homer to Roberto Alomar that led to a Game 4 comeback loss to the Blue Jays and an eventual series defeat.

“I don’t know what it is, you just remember the bad stuff, you just do,” Eckersley said on MLB Network’s feature film, “Eck, A Story of Saving.” “It’s not that it outweighs the good, because it just doesn’t. But it stays with you. Keeps you humble. I’ve had enough to be humble about.”

The humility is what has made him so great on the air, with Eckersley unafraid to be honest about his playing days, admit his faults, share insight into his successes, and be just as candid about what he’s seeing on the field.

It’s what made him so friendly with broadcasters and media members, and simultaneously disdained by some of the more sensitive modern day big leaguers like David Price and Marcus Stroman.

It often seems as though the players who haven’t done the work on themselves, those who are afraid of being vulnerable or don’t believe observers have a right to be honest about what they see, are those who have been most offended by Eckersley throughout his broadcasting career.

Eckersley calls it like he sees it, but those who know him or know anything about him know this: it’s not born out of resentment or vindictiveness, but rather from a lifetime spent chasing the highs and surviving the lows in a sport that’s full of both.

“He was rash, cocky and great,” his former teammate Bruce Hurst said on the MLB Network special. “And he was honest. He never ducked an interview, never hid by any excuse.”

When the Red Sox were embarrassingly terrible in 2014 and 2015, then again in ’20, Eckersley said so. He made unwatchable games entertaining while connecting with Red Sox fans who demanded better from their team.

Eckersley cares deeply about the game. He cares about presenting it with style and keeping it interesting and entertaining.

Soon, he’ll care mostly about his grandchildren as he returns to the Bay Area to enjoy his retirement with his family.

His family in New England, those who allowed him into their homes so often over the last 20 years, will surely miss him.

You can bet the ranch on that.