Previously, he co-anchored CBS2 News at Six with Dana Tyler on WCBS-TV in New York[1] and co-anchored the News At Nine on CBS2's sister station WLNY, with Alice Gainer.

Before joining CBS2 Brennan was a political correspondent for Fox 5 News in New York City, and Brennan also serves as a fill-in & substitute anchor for CBS 2 News At 5:00 & 11:00.

[3][4] Before appearing on-camera, Dick was a producer for radio personality Bruce Williams, WWOR-TV and WNBC-TV.

He grew up in Queens, attended Archbishop Molloy High School, and then, graduated from Fordham University in the Bronx.

Brennan made a cameo appearance on the eighth season of 24, playing himself in two episodes.