A few years back, the Boston Red Sox moved on from their superstar despite them being in the prime of their career, only to watch them thrive on the West Coast.

While most people would surmise we were referring to Mookie Betts, who helped the Los Angeles Dodgers win two World Series championships, it would be an apt description of play-by-play announcer Don Orsillo as well.

Orsillo, a fan favorite broadcaster for the MLB club from 2001 to 2015, was shown the door on August 25, 2015, when it was announced that NESN would replace him with Dave O’Brien the following season. It was a stunning move for the franchise to gladly walk away from the voice of their three World Series championship seasons of 2004, 2007, and 2013.

At the time, the Boston Globe‘s Chad Finn reported that Orsillo, who was born in Massachusetts and considered this a dream job, “was never a favorite” of NESN’s new VP of programming. But given how near-universally he was beloved and admired, it was nearly impossible to find any support for the move. It also didn’t help that the Red Sox handled the switch about as poorly as one could, announcing O’Brien’s hiring minutes before Orsillo went on the air to call that night’s game. Team brass went on to throw Orsillo under the bus over how everything went down and confiscated fan signs in support of the broadcaster.

8 years and 6 months ago today, September 27, 2015, Don Orsillo worked his final game at Fenway as the TV voice of the Red Sox. He returns to Boston tomorrow night as the TV voice of San Diego Padres. pic.twitter.com/AZEIHoNyFr

— Boston Radio Watch®️ (@bostonradio) June 27, 2024

The San Diego Padres quickly snatched up Orsillo to be Dick Enberg’s successor, and he soon ascended into that role where he’s been ever since. Last week, Awful Announcing readers voted the Padres booth (Orsillo and Mark Grant) as the No. 1 local announcing booth in all of MLB.

The anger and disappointment from Red Sox fans over the move haven’t really dissipated over the years. Check the comments on any social media post of an Orsillo call, and you’ll still see someone bemoaning the fact that the Red Sox let him go.

NESN and the Red Sox certainly didn’t help matters when, in 2022, Orsillo was not included in a tribute ceremony at Fenway Park for longtime broadcast partner Jerry Remy, who had died the prior year. Team officials claimed that it was due to his obligations to the Padres. However, Orsillo responded on Twitter that he had submitted a video tribute that the Red Sox ultimately opted not to include in the ceremony.

Orsillo returned to Fenway Park in 2024 to call a game for the first time since being let go.

“I believe to this day that the broadcaster’s role is that of a family member,” Orsillo told MassLive’s Sean McAdam, “You truly become a family member. You’re on, in their livings rooms every night, every day. Or you’re on in the background while they’re doing something. You’re their voice of summer. The bond that people have with broadcasters is why I got into this business in the first place.”

The Red Sox chose not to honor Orsillo during that return, kicking off a fresh round of anger from a fandom desperate to recapture the glory days that he was the voice of (the team won the 2018 World Series but has missed the playoffs in four of the five seasons since).

For Orsillo’s part, he’s found peace and a home with the Padres, telling Awful Announcing in March, “I was here about 10 minutes when I realized this was where I wanted to spend the rest of my career.” He signed a long-term extension with the ballclub before the season.

In a memorable moment earlier this month, Orsillo and Padres shortstop Xander Bogaerts got a chance to remind the Red Sox what they’re missing when the former Boston star launched a home run against his former club, and the former Boston announcer broke out a classic call to match it.

Don Orsillo calling a Xander HR against the Red Sox genuinely destroyed my soul. pic.twitter.com/WmsGOauCYU

— Mike (@GMagz42069) August 10, 2025

“I love you Bogey!” wrote Orsillo on X afterward. “So glad we are together for both of our 2nd chapters and can’t wait to win another ring together.”

They might get their chance. The Padres are currently tied for the National League West lead and are primed for another playoff push this year. Regardless of how it turns out, there are plenty of Red Sox fans who still don’t understand why Orsillo might be calling a World Series season for someone else, and how they ever let him get away.