Will the OWS folks camp out in front of his house until he pays?
Mr Bryan, a former adviser to Bill Clinton who helped raise funds for Mr Obama's re-election campaign, has owed the money to the Internal Revenue Service (IRS) since 2006, according to court filings obtained by The Daily Telegraph from Texas.
Mr Bryan, who has been in a relationship with Ms Wintour since 1999, was also pursued for outstanding Texas property taxes, and has had energy companies he owns in the state chided by local authorities for falling behind on their financial filings.
The findings may threaten Ms Wintour's confirmation as a US ambassador if nominated by Mr Obama. Her appointment would need to be approved by the US Senate, which has in the past objected to irregularities in the tax affairs of nominees and their partners.
Mr Bryan, 66, was said to have a fortune of $30 million when he left his second wife, Katherine, for Ms Wintour 13 years ago. He reportedly suffered a decline in personal wealth amid the financial crisis, however, and frequently stays at Ms Wintour's $10 million townhouse in Manhattan.
Ms Wintour was one of Mr Obama's leading fundraisers during his re-election campaign, bringing in $500,000 to the president's coffers. At one $35,000-a-plate fundraising dinner in August, Mr Obama thanked "Anna and Shelby for being such extraordinary hosts".
Laws are for the little people.