Oracle Exec's 8-Year Affair Splashed All Over NYC

Bizarre billboards yanked late Friday afternoon

Oracle co-president Charles E. Phillips is a handsome dude. According to a recent magazine profile, the Manhattan businessman has a lovely wife, Karen Phillips, and son Chas.

So why is he popping up on gigantic billboards in the city (and elsewhere across the country) with his arms around another lovely lady, YaVaughnie Wilkins?

In a statement released through a spokesman, he confessed an affair:

“I had an 8½ year serious relationship with YaVaughnie Wilkins," the statement said. "My divorce proceedings began in 2008. The relationship with Ms. Wilkins has since ended and we both wish each other well."

The massive signs were plastered across the country, with three popping up in the city, along with one in Atlanta and one in San Francisco, before being taken down Friday afternoon. One of the three-story-tall billboards, placed strategically on the corner of 52nd Street and Broadway near Times Square, showed a warm, glowing photo of the couple below the words "Charles & YaVaughnie." The top of the giant ad declares, "You are my soulmate forever -- cep," and the bottom points people to a Web site that catalogs in meticulous photographic and video detail a long romance between Phillips and Wilkins dating back to at least 2001. The Web site was receiving a "service unavailable" error Friday morning, but was back up and running by about 12 p.m. 

The very public exposure of the affair couldn't come at a worse time for Phillips, a top dealmaker at the Redwood Shores, Calif.-based software company. The company is in the midst of getting a multibillion-dollar deal to buy Sun Microsystems through regulatory approvals.

While Phillips says he and Karen began divorce proceedings in 2008, evidence suggests that the couple may be in the process of reconciling.  According to Valleywag, a Silicon Valley gossip blog, Phillips recently appeared at an award ceremony in New York with Karen and effusively thanked his wife in his acceptance speech. And the two were photographed together at a gala held by the American Museum of Natural History in the city on Nov. 19, 2009.

Béla Kovács, the California-based designer of the Phillips-Wilkins website, told Valleywag it was commissioned as a gift to Phillips by Wilkins.

Since Phillips works for Oracle CEO Larry Ellison, one of Silicon Valley's most notorious playboys before his marriage to romance novelist Melanie Craft, it's hard to imagine Phillips's romantic intrigue having any impact on his job.

The scandalous billboards and long affair could have political implications, though. That's because Phillips was appointed to the Economic Recovery Advisory Board by President Barack Obama. Lord knows while there's plenty of hanky-panky in D.C., but it's generally not well-received by a nation at large full of heteronormative prudes and their fiercely monogamous mindset.

Nor will the publicity likely be received well by Phillips' wife, who lives with him and their son in a posh brownstone on the Upper West Side.

When a New York Post reporter knocked on their door yesterday, Phillips opened it and said, "Oh man," before shutting the door with an apology.

At the very least this is the sexiest, most dramatic story to come out of the database business since, well, ever.

Jackson West wonders if Oracle should have bought LiveJournal, since they clearly know from drama.

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