Inside The Red Sox

Red Sox's Controversial Off-Field Decision Still Hurts 10 Years Later

Sox fans may never get over this loss...
Jun 29, 2025; Boston, Massachusetts, USA; A closeup view of the Green Monster before a game at Fenway Park between the Boston Red Sox and the Toronto Blue Jays. Mandatory Credit: Eric Canha-Imagn Images
Jun 29, 2025; Boston, Massachusetts, USA; A closeup view of the Green Monster before a game at Fenway Park between the Boston Red Sox and the Toronto Blue Jays. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

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It's a phrased that's overused, but completely true: You never know what you've got until it's gone.

The Boston Red Sox hired Massachusetts native Don Orsillo to be their primary play-by-play man before the 2001 season, and for 15 years, the hometown favorite developed a special relationship with the fan base. But at the end of a disappointing 2015 season for the team on the field, the biggest loss of the year came out of nowhere.

Orsillo was mysteriously let go by the Red Sox and NESN, the team-owned television network, and quickly found a new gig with the San Diego Padres. It wasn't received well at the time, but the decision has only grown less popular over the years.

Don Orsillo, Padres named number-one broadcast in baseball

On Monday, Awful Announcing released their yearly Major League Baseball television broadcast rankings, and Orsillo and the Padres ranked first out of 30 teams. The site gathered over 31,000 responses to the poll that ultimately determined their rankings, and Andrew Bucholtz compiled feedback from some of the voters.

"Some of (the comments) included 'One of the few booths that can achieve unhinged humor,' 'Orsillo has been an ace for a long time, and Grant is a ‘quirky’ analyst who makes the game fun to watch,' 'Hilariously entertaining while simultaneously doing an excellent job announcing the game,' and 'Would give an A+ if I could. Orsillo and Grant are by far the best duo in the game,'" Bucholtz wrote.

"Indeed, the most common sentiment in these comments was the idea of “best.” There were at least 65 usages of either 'best' or 'GOAT' for this booth, far more than we saw for any other announcing team."

Meanwhile, the Red Sox ranked 11th, which was actually a step up from their 16th-place standing in the site's poll from a year ago. But there was still some criticism for play-by-play man Dave O'Brien, who took over for Orsillo at the beginning of the 2016 season.

"O’Brien, who the team tabbed as their lead play-by-play voice to replace Don Orsillo ahead of the 2016 season, drew particular discussion in the comments. Some of that was positive, including 'first rate,' 'a consummate pro,' and 'the best,'” Bucholtz wrote.

"But others went in on him with lines such as 'so boring,' 'has no personality,' and 'If you had AI create a baseball announcer, it would spit out Obie.' Many noted they’re still disappointed about Orsillo being gone, and several readers stated a preference for backup announcer Monaco, with one calling him 'a million times better than O’Brien could ever be.'”

Missing Orsillo doesn't necessitate a negative opinion of O'Brien. But it's abundantly clear from the data that Red Sox fans wish their team could have a do-over, and it's hard to see that sentiment changing with each year Orsillo thrives on the West Coast.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org