Sid Rosenberg started his radio career on "The Drive" heard strictly on the internet at SportsLine USA. The show eventually moved to terrestrial radio and was nationally syndicated in over 40 markets by SportsFan and Westwood One. Rosenberg also co-hosted the NFL Today pre-game show heard nationally on Westwood One for 3 seasons. After 2 years on national radio Rosenberg (and Kaplan) took their act to New York City where they hosted "The Sports Guys" show heard mornings on WNEW (102.7 fm). At the time WNEW was also home for the popular "Opie and Anthony Show", "The Radio Chick", and "Ron and Fez."

In 2001 Rosenberg realized his own dream by landing a job at the nation's premier sports talk station WFAN in New York City hosting Mid-Days and doing sports on "The Imus in the Morning Show". While at WFAN Rosenberg was the pre-game show host for the New York Football Giants for three seasons. Sid Rosenberg has also worked with the Daily News, CSTV, The Best Damn Sports Show, The New York Dragons and FOX online (just to name a few). Rosenberg has also made multiple appearances on many news shows including the "Joe Scarborough Show", "Hardball with Chris Matthews", the now defunct "John McEnroe Show" and CNBC's "Donny Deutsch Show." In November of 2005, Rosenberg relocated to South Florida and signed on with 790 The Ticket. He remained with the show until March of 2009. Currently, Sid is very close to signing on with WQAM 560 in Miami.