BOSTON — The question caught Dennis Eckersley off guard, which wasn’t a problem — it was the nature of a live broadcast — but for just a moment, the least filtered color commentator in baseball genuinely didn’t know how to respond. He could have said anything, which is to say that he could have answered almost any question.
The sixth inning of a lopsided game Red Sox game at Fenway Park last week, NESN play-by-play man Dave O’Brien steered the on-air conversation toward advice the veteran Eckersley might give to booth newcomer Will Middlebrooks.
“What would make me good at this job?” Middlebrooks asked.
Eckersley listened intently to the question, literally stroking his chin. It was a genuine, but almost theatrical display of thoughtful consideration.
“You know something,” Eckersley said. “Not being afraid to say what needs to be said.”
Eckersley has been saying the right things for more than two decades. But Wednesday will be his last day in the NESN booth. He’s retiring for the second time in his life. He retired as a player after the 1998 season — fittingly, his final year was with the Red Sox — and now he’s stepping away after 20 seasons with NESN. In 2003, he joined the studio as an analyst and was promoted to the broadcast booth in 2009. He’s 67 years old. His family lives in California. He has been away for many years. He would love to spend time with them.
“For all the right reasons,” Eckersley told The Athletic.
