According to MassLive’s Sean McAdam, O’Brien has quietly signed a two-year extension to remain NESN’s play-by-play voice for Red Sox broadcasts through at least the 2028 season, with his previous deal set to expire at the end of this year. O’Brien’s tenure in the Red Sox booth began under circumstances NESN would probably like fans to forget. Orsillo landed in San Diego, where his pairing with Mark Grant topped Awful Announcing’s own 2025 MLB local broadcaster rankings, while O’Brien’s Red Sox booth came in 11th. A decade later, O’Brien has established a steady, enduring presence in Boston, supplementing his Red Sox duties with national college basketball and football assignments for ESPN. A new deal carrying him through 2028 suggests NESN continues to regard him as the right steward for the booth.