[8] He admitted to not being in the booth when the ball rolled through Bill Buckner's legs in the 1986 World Series, as he was in the clubhouse covering Red Sox' seemingly impending victory celebration.
[11] After Starr's departure at the end of the 1992 season, Castiglione became the team's lead radio announcer along with Jerry Trupiano.
During the 2007 season, Castiglione shared announcing duties with a rotating duo of Dave O'Brien[13] and Glenn Geffner.
On September 20, 2018, as part of a promotion called "A Rivalry in the Booth", Castiglione switched places with New York Yankees radio broadcaster John Sterling in the fourth inning.
[19] For the 2023 season, Castiglione began working a reduced role, only calling 81 games as the primary announcer in order to spend more time with his family.
Castiglione was honored by the Red Sox on September 29 with a pregame ceremony,[22] as various players whom he covered over his 42 year stint showed up to pay their respects to his career.
Castiglione ended his broadcast as he traditionally did at the close of each season since 1989, reciting a passage by Bart Giamatti from the essay "The Green Fields of the Mind".
You count on it, rely on it to buffer the passage of time, to keep the memory of sunshine and high skies alive, and then just when the days are all twilight, when you need it most, it stops."
In August 2014, Castiglione was inducted to the Boston Red Sox Hall of Fame, along with former players Roger Clemens, Pedro Martínez, and Nomar Garciaparra.
Castilgione had also been nominated as one of the ten finalists in 2023, but the award was presented to Chicago Cubs broadcaster Pat Hughes.
[9] Castiglione has worked as a lecturer in the department of Communication Studies at Northeastern University, teaching a course on sports broadcasting.
[6] In 2004, Castiglione published a book called Broadcast Rites and Sites: I Saw It on the Radio with the Boston Red Sox.
In this book, he takes the reader back to the 2004 ALCS with the Yankees and that year's World Series as well as the team's return to glory in 2007.