Gossip Cop’s Firsthand Account: David Letterman And His Assistant Stephanie Birkitt In 2005

In September 2005, Gossip Cop‘s Michael Lewittes had a seemingly random encounter with David Letterman and his assistant, Stephanie Birkitt. Four years later — in the midst of Letterman’s affair/extortion super story — the serendipitous encounter seems less like a charming coincidence and more like a priceless insider’s anecdote.

To hear Lewittes tell it, it was like any other Emmy night: Los Angeles traffic was clogged and Lewittes, an Access Hollywood producer at the time, was running late. And so, clad in a tuxedo, he ditched his ride and started making his way toward the theater on foot. To his surprise, he saw a familiar face:

About three blocks away, I saw David Letterman, dressed in shorts and smoking a cigar, briskly walking away from the auditorium. With him was a woman dressed in black. That was Stephanie Birkitt, Letterman’s former assistant, with whom he had a sexual relationship, and who later took up with “48 Hours” producer Robert “Joe” Halderman, the alleged exortionist who reportedly used her diary and e-mails as proof of her relationship with Letterman in an effort to squeeze the talk-show host out of $2 million.

Despite intermittent urgings from Birkitt, Letterman tried to resist attending the show and even agreed to a quick chat on a bus bench with Lewittes for Access Hollywood, probably in an attempt to procrastinate from the night’s elaborate festivities. Lewittes describes noticing a “closeness” between Letterman and the woman we would later find out was his lover, but the whole story is beyond bizarre. Only in Hollywood!

Check out the entire account exclusively at Gossip Cop.