​Shelby Bryan: 5 Things To Know About Anna Wintour’s Ex As They Split After 20 Years Together

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After more than 20 years together, Anna Wintour and husband Shelby Bryan have called it quits. The Vogue editor-in-chief, 70, and the businessman, 74’s relationship had reportedly “cooled off” some time ago, according to The New York Post, but their split is now seemingly official. Here’s what you should know about Shelby as they end their two-decade relationship:

1. He and Anna got together in 1999. Shelby and Anna’s relationship began with a scandal. The two started seeing each other when they were both still married — him to Katherine Bryan, and her to David Shaffer. The affair crumbled both their marriages; the Vogue EIC and David divorced in 1999, and Shelby and Katherine divorced in 2001. Anna and Shelby went on to get married in 2004, and have spent 16 dedicated years by each others’ side.

2. He’s a renowned investor. Aside from his relationship with Anna, Shelby is best known as a successful businessman. He started his career in the field at Morgan Stanley in the 1970s, later starting his own cellular company in NYC called Millicom in 1980. From there, he moved to ICG and Pingtone. Shelby holds an MBA from Harvard Business School.

3. He has raised millions for the Democratic party. The lifelong Democrat has given hundreds of thousands of dollars to the Democratic party and its candidates since 1995, according to campaign finance watchdog group Texans for Public Justice. Shelby served as the National Finance Chair for the Democratic Senatorial Campaign Committee from 1997 to 1998. During that time, the committee raised over $54 million. He also served on the President’s Foreign Intelligence Advisory Board from 1999 to 2001. In the 2000 election, he supported friends Al Gore, for president, and Hillary Clinton for New York senator, according to Texas Monthly.

4. He’s been married three times. Shelby was married to Lucia Bryan sometime in the late 1970s, though the exact date is unknown. They had two daughters together: Ashley and Alexis. Their relationship ended in divorce. Shelby married Katherine in 1984, and they had two sons: Austin and Jack Bryan. Their marriage ended in 2001 after Shelby started his affair with Anna.

5. He’s a patron of the arts. Shelby is a financial contributor to the New York Metropolitan Opera, the Houston Fine Arts Museum, and the Houston Grand Opera. In the late 1980s, he also served on the board of the famed Actors Studio. And in 1983, he co-produced the off-Broadway play The Last of the Knucklemen.