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The D.C. businessman at the center of an ongoing city corruption investigation secretly spent more than a half-million dollars on get-out-the-vote efforts for Hillary Rodham Clinton’s 2008 presidential campaign, according to interviews and court documents filed Wednesday.

Jeffrey E. Thompson, a former city contractor who allegedly financed a secret campaign for then-mayoral candidate Vincent C. Gray (D) in 2010, financed an independent effort to reach urban voters on behalf of Clinton in Texas and at least three other states during the 2008 Democratic primaries, according to the interviews and documents.

Thompson allegedly paid Troy White, a New York marketing executive, more than $608,000 to hire “street teams” to distribute posters, stickers and yard signs beginning in February 2008 to help raise Clinton’s profile during her primary battle with then-Sen. Barack Obama, according to the documents and interviews with several people familiar with the investigation.

A search of federal campaign records found no evidence that Thompson or White disclosed the alleged expenditures or activities to the Federal Election Commission, as required by campaign finance laws.

The new accusations came to light when White pleaded guilty Wednesday to a misdemeanor tax charge, becoming the latest Thompson associate implicated in a far-reaching investigation that has explored the businessman’s alleged secret role in funding political campaigns.

For the first time, the investigation has connected Thompson to a major national political figure. The investigation could have implications for Clinton, who is weighing a second run for president in 2016 and is seen as an overwhelming favorite for the Democratic nomination.

Thompson’s attorney, Brendan Sullivan, declined to comment.

An attorney for Clinton’s 2008 campaign, Lyn Utrecht, said in a statement late Wednesday that the campaign “has cooperated fully” in the White case.

A senior official on Clinton’s 2008 campaign said no one in the campaign’s senior leadership or with budget-making authority knew about White’s independent canvassing campaign. Other senior officials said they had never heard of White.

“I’m absolutely certain he had nothing to do with any of us,” said Garry Mauro, chairman of Clinton’s Texas campaign. “I was at the headquarters almost every day, I traveled the state, and I never heard of this guy.”

The allegations that Thompson secretly helped Clinton in Texas and at least three other primary states in 2008 are similar to allegations about activities surrounding the Gray campaign. Two of those states were North Carolina and Indiana, according to people familiar with the case. The fourth state was unknown.

Prosecutors have been building a case against Thompson, who has been described in court documents as the financier of a secret campaign for Gray’s successful run for mayor, and court records show that he is the subject of a grand jury investigation.

Neither Thompson nor Gray has been charged, and the mayor has denied any wrongdoing. Thompson has not been named in any of the documents, but several people with knowledge of the case have identified him as the businessman in those documents.

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Court documents and interviews indicate that in early 2008, as Clinton struggled to make up ground against Obama in the primaries, White directly approached the Clinton campaign, pitching his ability to help organize supporters in urban areas. After campaign officials declined his services, a longtime Clinton adviser, Minyon Moore, helped connect White with Thompson, who agreed to fund his canvassing operation, according to the documents and interviews.

Utrecht, the Clinton campaign attorney, emphasized in her statement that the campaign “turned down Mr. White’s services.”

Moore is not identified in the documents, but several people with knowledge of the case said she is the campaign official described in those documents.

Moore, who began her career in Chicago as an organizer for Jesse Jackson’s 1988 presidential campaign and for Jackson’s Rainbow PUSH Coalition, became one of the Clintons’ closest political advisers. She served as director of political affairs in the Clinton White House and later as chief executive of the Democratic National Committee.

On Hillary Clinton’s 2008 campaign, Moore was a senior adviser, working closely with many departments of the campaign, and she was particularly instrumental in African American outreach. She was one of the District’s 21 “superdelegates.”

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