Sidney Rosenberg was one of the original Sports Guys that made up the team of Scott and Sid. Sid lasted on the show for about a period of one year. For the first 6 months, he was paired up with Scott Kaplan. Shortly after Eddie Ifft's arrival Scott left and Sid did the show with Eddie Ifft as they searched for new hosts. Eventually Craig Carton and Blaine Ensley would become Sid's new partners as Eddie was phased out. Sid's love for New York Sports with an extremely funny personality made him a must listen to in the mornings. Sid eventually left the show when he and management agreed to mutually depart ways.
Following his departure from the Sports Guys, Sid landed on WNEW's sister station, WFAN as a weekend sports host and as the Sports Reporter on the Imus in the Morning Show. Sid's sense a humor made this a natural fit on Imus. Sid's career almost went into a major tailspin when he made some negative comments on Serena and Venus Williams. WFAN removed Sid from the air, however Don Imus who liked Sid convinced management to let him back on and Sid issued an on-the-air apology. Sid's hard work would eventually payoff when he would become the mid-day host with long time WFAN personality Jody McDonald. He continues to work the Imus show as well.