Brenly had worked from 1996 to 2000 and called the 1996, 1998, and 2000 World Series alongside Joe Buck and Tim McCarver and the ALCS and All-Star Game in 1997 and 1999. However, he provided analysis and reporting from the stands in the 2000 World Series). He was then hired in November 2004 to replace Steve Stone as a color analyst for televised Chicago Cubs games. Brenly teamed with play-by-play announcer Len Kasper. He had previously teamed with Harry Caray, Thom Brennaman, and Ron Santo during the 1990 and 1991 seasons on radio. He often jokes about his mediocre playing career. Brenly is often referred to by his nickname, "BB" and was rumored to be in the running for several managerial positions for the 2008 season, though nothing materialized. Brenly was in the running for the 2009 Milwaukee Brewers managerial position and was said to be the favorite, but the job went to Ken Macha instead. 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. Brenly again worked Division Series post-season coverage for TBS in 2009-2013 with Dick Stockton as his play-by-play partner each year. He opted out of an extension to his contract with the Cubs and WGN television on October 17, 2012. On October 18, 2012, Brenly signed a five-year deal as the TV color commentator for the Diamondbacks. On June 3, 2021, Brenly announced in a statement that he'd be stepping away from broadcasting for a temporary basis to reflect on comments he had made the day before on-air about New York Mets pitcher Marcus Stroman, which Aramis Ramirez said was discriminatory. Personal life Bob Brenly married Joan Brenly on August 10, 1974; they have two children. Their son Michael was drafted by the Chicago Cubs in 2004 (out of high school) and 2008 (out of UNLV) as a catcher. He played in the Cubs and Boston Red Sox minor league systems in all or parts of eight seasons spanning 2008–2015. After retiring from the Portland Sea Dogs in May 2015, the younger Brenly took a position as the assistant bullpen catcher in the Boston organization.