In 2007, Brenly served as a game analyst during postseason broadcasts on the TBS cable television network. He covered the Yankees–Indians series in the ALDS and the Rockies–Diamondbacks series in the NLCS alongside Chip Caray and Tony Gwynn. On September 13, 2008, Brenly signed a four-year extension worth $3.5 million to continue his role as color analyst for Cubs games.