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Mr. Bailey has portrayed himself as a banker, but his 15-year career at Fannie Mae ended with him as a vice president of human resources, where he was responsible, among other things, for strengthening the company’s diversity activities. Prior to that, he served the agency as a human resources director and a business analyst.

A key aspect of his government service, according to court records, is that while at Fannie Mae, Mr. Bailey frequently complained of wrongdoing by others. When his career path was stunted, he claimed to be a victim of racial and gender discrimination and complained of a hostile work environment. His allegations resulted in a five-year battle in and out of federal courts that neither he nor the agency will discuss.

Mr. Bailey declined to respond to numerous questions for this articlesubmitted in writing to his attorney, Edsel Guydon.

At a time he said he was averaging a 50-hour workweek at Fannie Mae, according to a Post profile, Mr. Bailey also was moonlighting to book jazz and R&B vocal acts into a Silver Spring, Md., nightclub, which he and a partner acquired in 1995 and renamed Bailey’s Cafe and Grill.

But Mr. Bailey’s stint as a nightclub owner was short-lived. He forfeited his liquor license in 1999, according to Montgomery County Department of Liquor Control records. And when the business folded that same year, he left behind more than $90,000 in claims, judgments and tax liens - some of which remained in litigation until last year, Maryland court records show.

When Mr. Bailey left Fannie Mae in 2007, he wasted little time in coming to the rescue of a struggling facilities management company, according to a Post profile.

Wilson Technologies was managing a sole-source contract to clean floors at Walter Reed Army Medical Center when Mr. Bailey came along. Mr. Bailey told a Post reporter he saved the company by investing $138,000 and obtaining a $250,000 line of credit.

But a 2007 lawsuit filed by a former subcontractor paints a less righteous picture. The lawsuit said that after Mr. Bailey joined the company, a contracting officer at Walter Reed imposed higher performance standards for the company to adhere to or lose the contract.

According to the lawsuit, Mr. Bailey told Wilson Technologies’ subcontractor that he could “get rid of” the contracting officer, adding that he “had made a living getting rid of people” like the officer.

The lawsuit said Walter Reed officials concluded that Wilson Technologies was understaffed, had inadequate quality controls and had “no experience with providing cleaning services.” It also said the company overcharged the Army for cleaning services, hoarded profits and engaged in a “scheme” to defame and drive out the subcontractor that did the actual work, Fresh Air Duct Cleaning.

An attorney for Fresh Air Duct Cleaning confirmed that the case settled out of court, but declined to elaborate.

“It’s not in my interest or my client’s interest to comment,” said the lawyer, Nicholas Hantzes, of Centreville, Va. Walter Reed officials did not return calls for comment.

Another Bailey partner, Emmanuel O. Irono, president of Motir Services, which formed a joint venture in June with Wilson Technologies on a cleaning contract at Ronald Reagan Washington National Airport, said he ended the partnership after less than a year because Wilson Technologies “could not fulfill its financial obligation.”

Mr. Irono said the airport deal required “a higher line of credit than Wilson Technologies had,” adding that a split was necessary to preserve his company’s reputation in the event of a default by Wilson Technologies.

After winning the lottery contract, Mr. Boothe, the Intralot vice president, said the firm still needed a local partner to get council approval. It was then that former D.C. Council member Kevin P. Chavous, an Intralot lobbyist, recommended Mr. Bailey, despite his business scrapes and lawsuits.

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