Anna Wintour’s Ex Shelby Bryan Was In Major Debt Before Their 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.