One of the Red Sox’s most regrettable, overlooked decisions just reared its ugly head

Don Orsillo became NESN’s voice of the Boston Red Sox at memorable time. He called Sox games from 2001-2015, throughout the team’s best years, as they claimed three of their MLB-leading four World Series championships since 2000.

Orsillo departed NESN on some sour terms, as the network opted not to renew his contract for the 2016 season and beyond. Red Sox fans are still unwell about the departure, especially because Orsillo and the San Diego Padres booth, which he has led since 2016, placed first on Awful Announcing’s ranking of MLB’s best local broadcast teams for 2025.

Orsillo and Mark Grant, his most common analyst counterpart, beat out SNY’s Gary Cohen, Keith Hernandez, and Ron Darling as well as NBC Sports Bay Area’s Duane Kuiper and Mike Krukow for the No. 1 spot. Orsillo and Grant are new to the “best booth” title this year, and they earned a staggering 1,047 “A” ratings out of 1,507 votes.

They fared better than Boston’s current play-by-play combo, Dave O’Brien and Lou Merloni, who placed 11th in Awful Announcing’s rankings. O’Brien received some praise from voters who called him “a consummate pro,” but he also took some heat for his calls being on the boring side, and plenty of Red Sox fans agree.

Awful Announcing names Padres booth, led by former Red Sox annoucner Don Orsillo, best in the league

Into the San Diego night!! pic.twitter.com/qmESVWERJi

— San Diego Padres (@Padres) May 14, 2025

Not only does Orsillo have a distinct voice that Red Sox fans still associate with most of the team’s best moments from the 2000s and 2010s, he was born in Massachusetts and raised in New England, with a special connection to the team. O’Brien was a longtime radio voice of the Red Sox and a New England native, but the excitement Orsillo brings to any broadcast is second to none.

Red Sox fans still embrace Orsillo whenever he comes to town, whether it’s to call a national Sox game or if the Padres are in Boston. In 2024, he called a game at Fenway Park as an opposing broadcaster for the first time in his career, and told MassLive that he posed for around 30 pictures on his walk from his hotel to the ballpark.

Red Sox fans yearn for the nostalgia of their best winning years in the early 2000s, and Orsillo was a huge part of them. Unfortunately for Boston, the Padres signed Orsillo to a long-term deal before the 2025 season, and team CEO Erik Greupner said he hopes the broadcaster finishes his career in San Diego.

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