A convicted white-collar criminal once connected to some of America’s most prominent political families pleaded guilty in federal court on Monday to stealing more than $1 million from multiple south Louisiana car dealerships over a three-year period, billing them for advertising services never rendered and sweeping the fees into his own bank accounts.

Raymond Christopher Reggie, a Mandeville businessman who previously worked on many high-profile Democratic campaigns, including those of former President Bill Clinton, agreed to a guilty plea in Baton Rouge federal court to five counts of mail fraud related to the illegal billing scheme, the U.S. Attorney’s Office announced. This is Reggie’s second federal conviction; he was sentenced to a year in prison about a decade ago for bank fraud.

In the current case, Reggie, 52, submitted more than 130 fictitious invoices to car dealerships, including Super Chevy Dealers of Baton Rouge and Supreme Automotive Group, which has dealerships in Gonzales, Plaquemine and other locations in southeast Louisiana. Those invoices brought in $1.1 million between 2009 and 2012, according to the superseding indictment to which Reggie pleaded guilty.

In an unusual occurrence, Reggie’s guilty plea did not include the benefit of a plea agreement, the U.S. Attorney’s Office said.

Attempts to reach Reggie’s attorneys were unsuccessful Monday afternoon.

Reggie’s political ties are deep. His brother-in-law was the late U.S. Sen. Ted Kennedy. His father, the late Edmund Reggie, headed former President John F. Kennedy’s presidential campaign in Louisiana. Edmund Reggie, a longtime Crowley judge, also served as executive counsel during the second term of former Gov. Edwin Edwards.

In the 1990s, Ray Reggie raised millions of dollars for Clinton and former Vice President Al Gore. Reggie also attended Christmas parties at the White House during Clinton’s presidency.

But Reggie ran into trouble in the early 2000s.

The advertising consultant pleaded guilty in 2005 to one count of conspiracy to commit bank frauds that cost Hibernia National Bank of New Orleans $3.4 million — Capital One bought Hibernia that year — and Biz Capital of Metairie $3.3 million. U.S. District Judge Carl Barbier in New Orleans sentenced Reggie to 12 months and one day in prison in that case. The judge also ordered Reggie to pay full restitution to both banks.

Three years before that conviction, FBI agents approached Reggie while looking into the fraud allegations. Reggie was not immediately charged, though, and he began cooperating in an investigation of David Rosen, Hillary Clinton’s key fundraiser in her successful campaign to become a U.S. senator from New York. Rosen was acquitted on allegations of campaign improprieties.

Most recently, in August 2013, prosecutors charged Reggie in the fraudulent billing scheme with five counts of wire fraud and six counts of money laundering. Prosecutors later filed a superseding indictment charging Reggie with the five counts of mail fraud to which he pleaded guilty Monday, just before a trial on the matter was scheduled to begin in U.S. District Judge Shelly D. Dick’s courtroom.

Reggie’s sentencing date has yet to be set. He faces prison time and the possibility of fine payments, restitution and asset forfeiture.

Between 2009 and 2012, while operating Nexlevel Group, an advertising firm, Reggie submitted false expenses to the car dealerships. Reggie told the dealerships that he arranged advertising deals with both real and fake businesses, according to the factual summary for Reggie’s guilty plea.

Reggie conned the dealerships by convincing them that he would hand-deliver the payments for the advertising services, which never were rendered, to the real and fake businesses. Instead, he cashed the checks into his own accounts, the summary says.

In August 2012, Supreme Automotive Group confronted Reggie with evidence of fraud.

“Reggie admitted that he acted alone to divert SAG funds to his personal benefit and enrichment,” according to the summary provided by the U.S. Attorney’s Office.

He still faces state theft charges in St. Tammany district court based on some of the same allegations, according to news accounts. A trial on those charges is set for March.

Over several weeks, Reggie sent emails and text messages to one of the company’s owners, “admitting his wrongdoing, asking for forgiveness, and pleading that his conduct not be reported to law enforcement authorities,” the summary says.

“Being articulate, smart, charming, and connected are often characteristics seen in successful con artists, like this defendant,” Walt Green, the U.S. attorney for Louisiana’s Middle District, said in a news release. “The audacity of his fraud schemes is only outdone by his desperate attempts to deflect blame to others.”

Staff writer Faimon A. Roberts III contributed to this report. Follow Ben Wallace on Twitter, @_BenWallace.