Risky Business

An elite private school, a top-drawer law firm, and lots of lewd talk.

The email arrived just before lunchtime June 15. In it, a photo showed a tanned nude blonde bending over, underpants around her thighs. With seductive eyes, she gazed at the camera. Below the image was a list of her interests: "Role-playing, cuckolding, slaves, ATM piggies, verbal humiliation..." The subject line read, "Porn star... Jenny Santana Ballman want[s] a fight."

The email came from a 38-year-old Coconut Grove pilot and Internet-multimillionaire-gone-bust named Glenn Ballman. The sexpot in the photo was his wife, Jenny. Recipients included at least 30 parents of students at the elite St. Stephen's Episcopal Day School, where the couple's kids attend. The message also went to attorneys at one of Florida's most prestigious law firms, White & Case.

Some of the St. Stephen's parents were angry. Jenny had chaperoned field trips and attended morning flag ceremonies at the half-century-old school.

The email chronicles six days of text messages, apparently exchanged between Jenny and several men. It begins with the following note from her husband: "Times have been tight since the recession hit. [She] has been home alone for 28 days in May of 2009 when this starts. I am up in Canada starting a company, working very long hours, and sending everything home to make ends meet."

It continues with transcripts of text messages allegedly pirated from Jenny's BlackBerry. The first one includes conversations with men named Brad and Jeremy:

May 28

9:19 p.m.

Jenny to Brad: I am... I wish you were here.

Brad: Really? That would be nice... What would we do?

Jenny: I would love to talk and kiss for hours.

Brad: Sweet. Does it involve a Rolling Stones T-shirt?

Jenny: More bareback.

Brad: Delicious!!!

Side note from husband: "Are you kidding me? We're married with four kids and she's talking about doing more bareback with this guy?"

A few minutes later:

Jeremy: Just got home. Need to shower and have to get pretty for you. Lol.

11:05 p.m.

Brad: Did I lose you?

Jenny: Never.

Brad: You have questions to respond to.

Jenny: What's the question?

Brad: Do I have to share? And tell me more about the kissing.

Jenny: Share everything... I'm dying to kiss you.

Brad: Do I share you? You won't share me.

Jenny: No sharing... You are all I need.

Glenn Ballman is a big name in some circles. He's been profiled in BusinessWeek and the Seattle Post-Intelligencer. As a brash 24-year-old in 1996, he founded an e-commerce site called Onivia.com and raised $600 million in an IPO. Then, when the firm's value dropped in 2001, he sold it, "picked up a helicopter license," and planned an "around-the-globe voyage," according to the Post-Intelligencer. "Ballman in many ways epitomized the dot-com CEO of the late 1990s," the paper wrote, "young, passionate, and full of energy."

He eventually ended up in Miami and became CEO of a financial services corporation called Genesis Exchange. It's unclear when he met Jenny, but in 2006, the couple paid $900,000 for a home with a kidney-shape pool a few blocks from Biscayne Bay in the Grove.

The family, like many, has recently experienced financial problems. In 2008, the IRS placed a $1 million lien on their house. This past February, HSBC Bank began foreclosure proceedings. And though Miami-Dade court records show Glenn once owned a private plane, none is registered to him with the Federal Aviation Administration today.

Glenn's email to the lawyers and St. Stephen's parents claims Jenny had an amateur porn career and went by the names "SexyLexus" and "Lexus888." She allegedly posted videos on NiteFlirt.com, an adult site where users pay for erotic videos.

And it wasn't just Brad and Jeremy who sparked Glenn's anger. An attorney named Victor, who works at White & Case, also likes to text:

May 29

8:37 p.m.

Jenny: Just got home and can't believe I'm buzzing!! At a kid's birthday party!!

Victor: Am laughing. Sounds like a good party.

Jenny: I would love to cuddle with you right now, smell u, kiss u, talk to u.

Victor: And much more. Me too... Not sure if I can go a day without seeing you again.

Jenny: I'm dying.

May 30

9:25 a.m.

Jenny: Slept in :) This is crazy. I go to sleep thinking about you, I wake up thinking about you... coño!

Victor: Agree :)

Saturday May 31:

7:48 a.m.

Victor: You didn't have to "forget" your bracelets to see me again. I am hard this morning thinking of you. I have a problem. P.S. I don't want either of us to see other people and I know it is early in the relationship. It is just how I feel and I want to get it off my chest.

Jenny: You're so funny... I love that about you. I guess I have to see you again. I just realized u didn't say u only wanted to date me... Should I take it back, rico suave?

Victor: No, I only want to date you :)

Jenny: Happy now. :)

3:34 p.m.

Jenny: Miss me yet?

Victor: Am reading in bed — haven't left my house and haven't stopped thinking of you.

Jenny: I'm trying not to text u or call u. It's hard, but I hate playing the game, so there :) I'm going to grab dinner with a friend later. If you're around maybe I can see you.

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