Who

Whipple is the Wall Streeter who moonlights as a society reporter for NY1. Yes, he's that guy with the crazy eyebrows.

Backstory

George Whipple III has quite the pedigree: His family settled in America in 1630 and hosted Roger Williams at their Whipple House Tavern in Rhode Island. After a similarly pedigreed education—Choate, Columbia, Columbia Law—George worked as a patent attorney at Cravath, Swaine & Moore. In 1987, he quit the legal racket and spent the next seven years working as a freelance photographer for the New York Times Magazine, Harper's Bazaar and Town and Country. (He also took shots of naked debutantes for Playboy.) Cleaning up his act and turning back to law, in 1994 he joined investment bank Donaldson, Lufkin & Jenrette as an in-house attorney, and started moonlighting as a society and celebrity reporter for NY1 soon after.

These days Whipple is a managing director in the legal department at Credit Suisse, the company that acquired DLJ, and he's also a columnist for Jason Binn's Gotham. Of course, you can still catch him as the host of "Whipple's World" on NY1. It's a gig that seems to suit both Whipple and NY1 nicely. It's unlikely the local DIY-news network would shell out big bucks for a red-carpet reporter; Whipple is a rich guy who could care less what NY1 pays him as long as he has a platform to do his thing. He does accept a salary from NY1, in case you're wondering, although it's reportedly very modest and a pittance compared to what he makes at the bank.

Personal

In the late '80s Whipple was briefly married to Katherine "Kit" Tobin (a woman with quite the pedigree herself—her great-granddad founded the San Francisco Chronicle), then had a two-year relationship in the mid-1990s with an aquatic exercise instructor whom he met while on assignment at a racquet club. Alas, Whipple has yet to pass on the genes for those eyebrows. He lives in a theater district penthouse where he reportedly hosts wild, promiscuous parties full of young women. "Craft yourself a pseudonym and a back-story with alternative age, origin, sexuality or non-cyber existence… Our imaginations go wild over the casual encounters of Craigslist," read the invite to one such party.

True story

When he was 14, Whipple ran for supervisor of his hometown, Kent, NY. Since he was too young to drive, his parents had to drive him around so he could campaign. He lost, but the stunt landed him a spot on the Tonight Show alongside Johnny Carson.