Then-Democratic presidential hopeful Hillary Rodham Clinton shakes hands with a supporter during a rally after her victory in the Puerto Rican Democratic primary, in San Juan, Puerto Rico, on June 1, 2008. Court papers show that a longtime Clinton adviser personally sought and secured the funding for an illegal shadow operation to boost her 2008 presidential bid. (Brennan Linsley/AP)

A longtime adviser to Hillary Rodham Clinton personally sought and secured the funding for what prosecutors say was an illegal shadow operation to boost Clinton’s 2008 presidential bid, according to court papers released as part of a wide-ranging campaign finance investigation.

Washington businessman Jeffrey E. Thompson, who pleaded guilty Monday to federal conspiracy charges in a case that has focused largely on D.C. Mayor Vincent C. Gray’s (D) 2010 campaign, told federal prosecutors that Clinton aide Minyon Moore asked him to fund pro-Clinton efforts in four states and Puerto Rico costing $608,750 during the hard-fought 2008 Democratic presidential primary campaign, the documents show.

Thompson financed the operation through his accounting firm, at times funneling funds through a company owned by a longtime associate. A spokeswoman said Moore did not know that Thompson was funding the project off the books, adding that Moore had asked Thompson to raise money directly for the campaign.

Prosecutors said they had no evidence showing Clinton was aware of the efforts.

But Thompson, in his discussions with authorities, depicted Moore as playing a far more intimate role in the off-the-books campaign than was previously indicated — securing the money and helping guide the strategy by feeding internal campaign documents and receiving messages about the media coverage.

Court documents do not identify Moore by name, but she is referenced as “individual A,” according to people familiar with the investigation.

Moore’s alleged participation in the scheme could have violated federal campaign finance laws, which prohibit officers or agents of a campaign from soliciting or arranging for illegal contributions. Election lawyers said pursuing charges against Moore could be difficult, however, because the five-year statute of limitations has expired.

Ginny Terzano, a spokeswoman for Moore’s consulting firm, Dewey Square Group, declined to make Moore available for comment.

Terzano said Moore has been “fully cooperating” with the investigation and that she was “entirely unaware of any inappropriate activities.” She said Moore both obeyed the law and acted “with the highest ethical and professional standards.”

Moore’s connection to the Thompson case was first revealed in September when court filings indicated that she had introduced Thompson to a New York marketing consultant who had unsuccessfully pitched the Clinton campaign on the use of “street teams” to improve Clinton’s standing in urban communities. The consultant, Troy White, pleaded guilty to a misdemeanor tax charge in September as part of the ongoing investigation.

The new court filings, submitted as part of Thompson’s guilty plea, lay out internal e-mails and other details portraying Moore as a central player who asked Thompson to finance the operation and then provided him and White with internal campaign strategy.

Terzano challenged the court documents, saying Moore had asked Thompson to help raise money directly for the campaign to pay for a legal field program.

Moore, who worked as a senior staffer for President Bill Clinton and went on to serve as chief executive of the Democratic National Committee, is close to both Clintons. She has been expected to play a significant role should Hillary Clinton decide to run for president in 2016. Burns Strider, head of the pro-Clinton group Correct the Record and a Moore friend, said Tuesday that her standing in the Clintons’ circle is secure and dismissed the allegations as “statements by a guy being prosecuted.”

According to the court filings, the shadow effort for Clinton began in February 2008, after the campaign rejected an offer from White to provide street teams.

The documents say that Moore, who was a senior adviser to the Clinton campaign responsible for minority outreach, asked Thompson to fund the operation. The effort aimed to drive up voter turnout for Clinton in a string of key primary states as she was battling Barack Obama for the Democratic nomination.

The first target was Texas. Moore introduced Thompson to a Clinton supporter in the state identified in court papers as “individual C,” who, the documents say, helped put in place the street team and paid canvassers.

The operation included members of the League of United Latin American Citizens, according to people familiar with the investigation who spoke on the condition of anonymity because of the sensitivity of the situation.

LULAC, which describes itself as the nation’s oldest Latino civil rights organization, does not endorse candidates, but top members of the group personally supported Clinton.

The street team workers for Clinton were recruited by “individual B,” identified by people familiar with the investigation as Luis Vera, LULAC’S general counsel.

Reached Tuesday, Vera said he was about to undergo a medical procedure and could not immediately comment. “I haven’t seen anything that you’re talking about,” he said. “I didn’t even know that Jeff Thompson had pled guilty.”

Paloma Zuleta, LULAC’s director of communications, said the group was cooperating with the ongoing investigation and was “not at liberty to discuss the issue.”

The street team’s members distributed official Clinton campaign posters, lawn signs and stickers, according to the court papers.

Clinton won the Texas primary, but in the end Obama won more delegates in the state through the party caucuses held the same day.

The court papers say that Moore, Thompson and White collaborated on similar operations in Pennsylvania, Indiana, North Carolina and Puerto Rico.

Citing internal e-mails, the documents say that Moore fed the team information from the campaign to guide its efforts. On April 28, 2008, court papers show that she forwarded a campaign e-mail about plans for North Carolina to Thompson and White with the subject line, “This is what they will need in NC — Please advise.”

The documents quote White as replying to Moore and Thompson: “These are the cities we can cover in NC: Charlotte, Raleigh, Durham, Greensboro, Fayetteville, Wilmington, Winston-Salem. Let me know what you think ASAP.”

Thompson financed the operation, transferring money to White’s firm, Whytehouse Marketing, through a company run by Washington public relations consultant Jeanne Clarke Harris, the court papers say.

A spokesman for Clinton and an attorney for Clinton’s 2008 campaign did not respond to requests for comment about the off-the-books efforts described in court documents.

But at a Monday news conference announcing Thompson’s plea deal, U.S. Attorney Ronald C. Machen Jr. stressed that there was no evidence that Clinton knew about the illegal operations run on her behalf.

“We don’t have any indication that the candidate [Hillary Clinton] was personally aware of Mr. Thompson’s illicit activities,” he said.

The documents provide insights into little-known aspects of the closely watched 2008 Democratic primaries, including the role played by LULAC.

What appeared to be genuine grass-roots activities by the Latino rights organization are instead portrayed in the court filings as part of an orchestrated campaign by Clinton’s allies, financed by huge sums of undisclosed money.

Thompson, for instance, paid LULAC $50,000 to file a lawsuit in Texas, challenging the state’s process for choosing Democratic presidential delegates, the court papers say.

The documents also say that Thompson arranged for $150,000 to be transferred to LULAC to transport and lodge activists holding a protest in Washington, recording the payment as a charitable donation, according to the court papers.

Later that month, LULAC bused demonstrators from Florida to Washington, where they protested in front of the Democratic National Committee headquarters over the party’s decision not to seat the state’s delegates.

After the event, Vera sent an e-mail to Thompson and Moore with the subject line “Media Coverage Florida Voters,” the court papers say.

“There was a great event today organized by [LULAC] . . . Hundreds came to DC and demonstrated,” he wrote.

At the time, the protest appeared to be an outburst of genuine anger on the part of ordinary Florida Democrats upset that party rules would prevent their votes from counting in the nomination process.

Glenda O’Laughlin, 71, who took part in the demonstration, said participants were given a free bus trip to Washington and a free night’s stay at a hotel in Virginia before they were taken into the city and deposited in front of the DNC.

But, she said, the event seemed pointless.

“I said, ‘What am I supposed to do? Carry a sign?’ I felt pretty stupid,” she said. “I thought it was such a waste, so disorganized, so asinine.”

“It makes more sense now,” O’Laughlin added.

Alice Crites, Tom Hamburger and Ann E. Marimow contributed to this report.