The Craigslist Congressman and the Crossdressing Prostitute

Chris Lee's resignation from the House on Feb. 9 may be the quickest political downfall in history: It came just three hours after Gawker published a photo of Lee standing in the mirror shirtless, along with a story about how the married congressman dabbled in a little online dating on Craigslist.

Lee's sudden exit took many people by surprise. Hadn't other members of Congress admitted to worse than an unconsummated, PG-13 flirtation and managed to stay in office? It turns out Lee may have had good reason to step out of the spotlight so quickly: It wasn't just women that the Craigslist Congressman was hunting for on the Internet.

In the past two weeks, two D.C.-area transgender women contacted us, each with a separate story about exchanging emails with the ex-congressman. One sent us an ad that Lee allegedly posted on Craigslist in search of trans women; the other sent us a never-before-seen photo that she says Lee sent her after they started chatting by email. Taken together, they present a possible explanation to those who have wondered why such a tame "sex scandal" forced Lee's hand so quickly.

Fiona's Story

The Craigslist Congressman and the Crossdressing ProstituteThe first woman who reached out to us was a pre-op transgender woman from Arlington, Virginia who we'll call Fiona.

Fiona told us she replied to an ad that appeared in the "casual encounters" section of Craigslist in mid-January. She used Craigslist's "e-mail this posting to a friend" link to send the ad to herself, she explained, so even though the ad no longer appears on the site, she was able to forward us a copy:

Sexy Classy guy for passable TS/CD - m4t - 39 (Cap Hill)
Date: 2011-01-14, 8:55PM EST

New to area. Very fit classy, successful guy. 39, 6ft 190lbs, blond/blue. smooth hard body. Looking for a sexy ts/cd that i can spoil. I promise not to disappoint.

The Craigslist Congressman and the Crossdressing ProstituteCraigslist personals are removed within seven days of posting, so there's no way to verify what the ad exactly looked like.

But Google does cache index pages on Craigslist, and we were able to confirm that an ad with precisely the same headline was posted on the evening of January 14, which is convincing evidence that the ad is genuine.

Revealingly, the headline and ad itself contain many elements from Lee's first known Craigslist flirtation, including the words "fit" and "classy." It dates to the same evening Lee exchanged emails with the woman we told you about two weeks ago. And it even featured Lee's infamous shirtless Blackberry picture, albeit cropped to hide Lee's face. Yes, that's right: a member of Congress posted a personal ad seeking transsexuals and crossdressers and even included a picture of himself, all without thinking twice, apparently.

Fiona's case was both similar to and utterly unlike Lee's first dalliance, the woman whose story we shared with you earlier this month. "It was quite interesting when I realized the other one was black and 34, because I am black and 34." Unlike the other subject of Lee's interest, however, Fiona was not born a woman.

When we spoke to Fiona by phone, she sounded entirely genuine. She told us that she'd corresponded with Lee by email several times and he told her that he'd dated a transsexual woman while "in college in California." (Lee went to business school at Chapman University in Orange, Calif.) Fiona said she found out who Lee was much the same way the other Craigslist correspondent did. "I copied and pasted his email into Facebook, and that's when his picture of him and his wife and his little boy showed up. Then I clicked on the link and realized he was a politician from New York, and I was like OMG."

She emailed him a few more times before telling him in an email on January 21 that she knew who he really was. He never replied, Fiona says.

The Craigslist Congressman and the Crossdressing ProstituteInterestingly, it was late in the afternoon on Jan. 21 that Lee sent an email to his staff informing them that his Gmail account may have been hacked. A copy of the email was provided to Gawker by Lee's spokesman two weeks ago when we first started asking questions.

We pressed Fiona for more evidence of their online flirtation. She said she would retrieve her emails and forward them as soon as she had time. But as the days went by, Fiona grew increasingly nervous. She was worried about being unmasked. And after corresponding with us for more than a week, Fiona went silent.

Holly's Story

The Craigslist Congressman and the Crossdressing ProstituteThe other person who contacted us shortly after our story was published was a transvestite who lives and works in Washington, D.C. We'll call her Holly.

The first thing Holly sent us was a never-before-seen picture of Chris Lee's now-familiar torso and red Blackberry. She edited the picture to obscure the Congressman's face, however, and printed her email address over his chest. (We have covered up the address in the photo above.) If we wanted to publish the unedited image, Holly explained, we'd have to pay her for it.

It didn't take very long to determine that Holly was a prostitute. We found a profile for her on an escort website which featured the same email address that she'd used to contact us. When we asked about her chosen line of work, Holly confirmed it. She was a working girl, she explained, and a man using Lee's email address had responded to a "Trans for Men" ad she'd posted on Craigslist.

We exchanged emails with Holly for more than a week in an effort to get her to share the email exchanges she had with Lee as well as the photos he sent her, including an unedited version of the picture she sent us at the outset. But even after we agreed to pay her the amount she'd requested for the material, she had trouble deciding if she wanted to follow through. "I kinda feel sorry for him at the moment," she wrote in one of her last emails to us before disappearing much like Fiona.

But while we never had a chance to review her emails with Lee and the photos that Lee allegedly sent her, the one, obscured photo she did send clearly resembles the Craigslist Congressman. The man in the photo has the same physique and is standing in the same pose. And he's holding the same red Blackberry, although the photo was clearly taken in a different setting and he's wearing different pants.

The Craigslist Congressman and the Crossdressing Prostitute

How did this transvestite hooker get a picture of the shirtless Congressman? It's conceivable she misrepresented herself online to acquire the pictures, or that someone else sent them to her. But that wouldn't explain how two separate transwomen approached us with similar—but not identical—stories. And it wouldn't explain the Craiglist ad that was posted January, three weeks before news of Lee's Craigslist shenanigans first went public, which seems both authentic and written in Lee's style.

Lee has been in seclusion since images of him flexing his bicep in front of a bathroom mirror traveled across the world. He's yet to speak out publicly about the incident, except to say in his letter of resignation that he made "profound mistakes" and "regret[s] the harm that my actions have caused my family, my staff and my constituents."

But if Lee was using the Internet to meet up with transgender women, it now makes a lot more sense why he would have decided to resign so quickly: Lee may have thought if he quit the House immediately, he'd be able to avoid having his "secret" exposed and spare himself any further embarrassment. No such luck.

Previously

Married GOP Congressman Sent Sexy Pictures to Craigslist Babe
Congressman Chris Lee Resigns Following Gawker Revelation
Craigslist Congressman's Would-Be Lover Speaks Out