In 2000, he returned to New York City to co-host WNEW-FM's turbulent morning show, the Sports Guys.

He engaged in heated half-mock, half-serious disputes with the other members of the Imus cast, leading for example to an actual boxing bout with producer Bernard McGuirk.

"[6] Rosenberg was fired from the Imus show after making crude remarks about Australian singer Kylie Minogue's breast cancer diagnosis.

This served as a lead-in to Imus and other cast members, who made comments that resulted in the cancelation of the program one week later.

[13] Rosenberg returned to WFAN on Saturday, February 6, 2010 to host a special Super Bowl preview show from Miami.

On Saturday, March 27, 2010 Rosenberg again returned to WFAN hosting a show in Port St. Lucie before the New York Mets faced the Washington Nationals.

He also completed two weeks of fill-in work with Kimberly Jones, Marc Malusis and Anita Marks on WFAN in July 2010 from 10:00 a.m. to 1:00 p.m. for Joe Benigno and Evan Roberts, who themselves were filling in for Mike Francesa from 1:00 to 6:30 p.m. WFAN's Mark Chernoff told Newsday of Long Island's Neil Best that he was very impressed with Sid's return to the FAN,[14] but that there was very little he could do to make the temporary hosting in New York anything more than temporary.

[15] In 2012, Craig Carton welcomed Rosenberg back, who CBS had neglected to invite to WFAN's 25th Anniversary celebration.

[17] On January 27, 2016, Rosenberg officially returned to New York radio as co-host of The Bernie and Sid Show of 77 WABC with Bernard McGuirk.

Rosenberg, who is a cousin of former Minnesota senator Norm Coleman, attended the University of Miami and Brooklyn College in 1984 and 1985 but dropped out of both.