Anna Wintour's Ex Shelby Bryan Was In Major Debt Before Their Split

Longtime Vogue editor-in-chief Anna Wintour (aka the Ice Queen of fashion) is famous for being a formidable powerhouse, but even she makes mistakes. Case in point: Her sordid extramarital affair with then-married telecommunications magnate John "Shelby" Bryan. 

The story goes that the pair met at a gala for the New York City ballet in 1997 and immediately hit it off. But all hell broke loose when an uncharacteristically unkempt Wintour was spotted leaving the luxury Parc Vendome apartments with Bryan early one morning while donning a decidedly evening-time Chinchilla wrap. Certainly, a fashion faux pas Wintour would never have committed under any other circumstance. "There are certain things that no one wants to read about in the tabloid press," Wintour later told New York Magazine in 1999, seemingly alluding to the media storm frenzy surrounding the affair. "You know that your friends and your family have one vision, and if the outside world has another, then that's just something that you just don't focus on."

Alas, even after subsequently divorcing their spouses and enjoying more than twenty years together, the star-crossed lovers eventually went their separate ways, with a source confirming the news in 2020. And to make matters worse, it's rumored that the once-affluent Bryan was in major debt prior to their famous split. 

Back in the nineties, John "Shelby" Bryan was famous for being tall and Texan but with a waspy flair, charming, well-connected, and old-moneyed to boot. But as we all know, the bigger they are, the harder they fall. And in 2000, it became apparent that the telecommunications titan had finally bit off more than he could chew by way of a $750 million deal with mega-money investors John Malone, Thomas Hicks, and Eric Gleacher. Seemingly overnight, the stock in Bryan's telecommunications company, ICG Communications Inc., nosedived from $39.25 a share to less than $1. Bryan was promptly ousted from his role as CEO in August 2000, and the company filed for bankruptcy in November of the same year.

Alas, that was only the tip of the iceberg when it came to Bryan's mounting money woes. His divorce from Katherine Bryan, with whom he was married for seventeen years and shared two children, proved particularly expensive for the businessman. It was reported that following the divorce, Katherine was set to make off with the profits from their shared marital properties, including their sweeping six-story townhouse in New York City and their sprawling estate in East Hampton. 

Perhaps, however, the only two things that genuinely scare John "Shelby" Bryan are Anna Wintour and the IRS. In 2013, it came to light that Bryan owned the IRS more than $1.2 million in property taxes. According to documents obtained by The Telegraph, Bryan's outstanding balance to the United States government dates all the way back to 2006 and originally totaled a staggering $1.6 million. Fortunately for Bryan, he had been slowly but steadily chipping away at the debt. "I've paid Harris County so much money in so many taxes," he lamented. However, he was adamant that he was still "on schedule" with his payments and admitted that the only reason he hadn't made good on the debt completely was because he simply "'didn't have the cash," according to the Daily Mail. YIKES.

To make matters worse, all of this just so happened to come out in the press at the same time there were whispers that Wintour was being considered for the role of U.S. Ambassador to Britain. Undoubtedly, it's not a good look for Wintour to have a boyfriend who is in the red with Uncle Sam. While we don't know exactly when Wintour and Bryan parted ways, many argue that Bryan's financial problems did play a role in the eventual demise of their relationship. Well, that and her work, of course. "It's no surprise Anna dumped him," a source told the Daily Mail. "Anna gets bored, and her career takes precedence over all."