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Campaign operative's past looms large in his future with next D.C. mayor

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By Nikita Stewart and Mike DeBonis
Washington Post Staff Writers
Saturday, November 20, 2010; 7:53 PM

His ability to gather people and raise money for a nascent campaign got Reuben O. Charles II noticed - and promoted. Even his impeccably dressed frame exuded a booming confidence.

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He was a top choice to be D.C. Mayor-elect Vincent C. Gray's chief of staff, in position to wield considerable influence in the new administration.

A few weeks and some missteps later, Charles, 41, continues to manage Gray's transition, but he is out of the running for the top job.

Charles's breakneck rise through the ranks of the Gray mayoral campaign was so fast it rendered the staff unable to control the public scrutiny of Charles's past. A decade ago, he was an ambitious venture capitalist in St. Louis, where a major deal to help minority businesses collapsed. The fallout - a series of lawsuits and liens - has haunted Charles. Just last week, he obtained a signed affidavit to clear him of a $236,000 debt to the state of Illinois.

The rocky financial history led some to pressure Gray (D) to distance himself from a man pivotal to his defeat of Mayor Adrian M. Fenty (D). It didn't help that in Charles's first week as head of the transition, Gray's election-night victory party was held at a nightclub owned by a man who owes the city more than $600,000 in back taxes. Gray also did not attend the funeral of the first police officer to die in the line of duty in two years. The blunders have caused some in the campaign to doubt whether Charles is ready for prime time.

"We made some mistakes, and I own up to them," said Charles, a married father of two elementary school-age boys who moved to the District three years ago.

But Charles's supporters fear Gray folded too easily to pressure from critics who say Charles lacked the experience and maturity to be chief of staff. Charles, they said, deserves credit for fundraising and for gaining the trust of education reform stakeholders worried that a Gray mayoralty would slow progress in schools.

In an interview, Gray downplayed the controversy surrounding Charles's apparent fall from grace. That Charles would be his chief of staff, Gray insisted, was a rumor that spun out of control. He credited Charles with doing "an excellent job during the campaign" but said he is unsure whether Charles would hold an administration post.

'Out of nowhere'

In an interview, Charles said he joined Gray's campaign in the spring as a volunteer because he was inspired by the council chairman's approach to government over that of Fenty. Gray, he added, "injected warmth and community sensitivity."

An IT consultant to District government and the Washington Metropolitan Area Transit Authority, Charles jumped at the chance to help campaign manager Adam Rubinson and Suzanne Peck, assistant manager and chief information officer at WMATA, who also volunteered to help with fundraising.

"When he came, he came out of nowhere," Neil Richardson, a Gray campaign strategist, said of Charles. "We saw pretty quickly that he was good at gathering people up."

Fenty's aggressive fundraising team, led by campaign manager John Falcicchio, had locked down hundreds of $2,000 maximum donations from developers and business interests reluctant to give to Gray.


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