Never before, though, has he gone this far to have the best of both his media worlds:
Since early January, he has spent mornings doing half-hourly sports updates on WINS (1010 AM), the all-news powerhouse, and afternoons doing his talk show on WQAM in South Florida.
"How many guys can boast doing morning drive in New York and afternoon drive in Miami ?'' he said.
Only one, presumably. Fortunately for Rosenberg, he never has lacked for energy.
He said his days begin at about 5 a.m., when he walks into his den in Boca Raton , reads the New York papers on his iPad and is "ready to rock'' for reports from 6:15 to 9:45 a.m.
After that, he typically goes for a long run, then is at WQAM's studios before 1. His show, which heavily covers New York teams in addition to South Florida ones, is on from 3 to 7.
WINS approached Rosenberg for the job after Jerry Recco left it to focus on his primary role as the update man on the morning show at WFAN, another CBS Radio -owned station.
It initially seemed like an odd fit, given Rosenberg's edgy personality and comic touch, and WINS' decades-long reputation for nuts-and-bolts news. Mostly, though, he plays it straight.
"It's not like I'm going to take this and start talking about porn stars in the morning," he said.
Instead, Rosenberg has used New York-related material from his Florida show to add depth to his WINS segments.
(When Giants safety Antrel Rolle criticized Tom Coughlin's style recently, he did so in an interview with Rosenberg on WQAM.)
Rosenberg rejected the notion that the WINS gig is another step in rehabilitating his image at CBS Radio - which he left in 2005 during a period in which he struggled with substance abuse - with an eye on a return to WFAN.
He noted he filled in on two dozen or so shows on the FAN last year, mostly in the summer.
"I don't think I need 1010 WINS as a transition,'' he said. "I think it's obvious we've established the relationship with WFAN.''
Not that that means he's angling for a full-time return. He recently re-signed with WQAM through 2012 and said, "More than ever, I love it.'' But the WINS offer proved too appealing to pass up.
"This is one of the greatest stations in the history of our medium,'' Rosenberg said. "It's a New York presence on a daily basis, which is something I'm thrilled with. It's also a paycheck. Why not?''