The trustee handling the bankruptcy of an energy-trading company run by former Iowa State wrestling star Timothy Krieger accuses Krieger of multimillion-dollar fraud in a new lawsuit, claiming he used a convoluted restructuring scheme to loot his own companies’ coffers, bankroll his lavish lifestyle and leave unsuspecting investors holding the I.O.U.

Krieger has denied wrongdoing.

But U.S. Trustee Randall Seaver said in a lawsuit filed last week that Krieger siphoned $20 million from Krieger Enterprises and its subsidiaries over a nearly three-year period between January 2015 and November 2017, at a time when his company was experiencing enormous operating losses.

In the ongoing battle, Seaver now accuses Krieger of 11 acts of wrongdoing, including five counts of fraud.

Reached Monday, Krieger said he had been out of town and was not aware of the latest legal action against him. The restructuring, he said, went through all the proper channels, including the Securities and Exchange Commission, auditors and tax accountants.

“We felt we did everything properly,” he said, later adding, “Businesses fail.”

The heart of the most recent claim against Krieger is a restructuring plan and loan related to various energy-trading startups he operated.

In July 2015, Krieger Enterprises took out a $22 million term loan from Aspirity Financial, a publicly traded company in which Krieger was also 99.5% owner and officer.

More than 700 individuals had invested about $30 million in Aspirity through a complicated financial instrument known as RUSNs, or renewable unsecured subordinated notes. RUSNs essentially are junk bonds with high risk and potentially high yields.

Krieger presented investors with a restructuring plan that assured repayment of the notes.

But it was all a ruse, the lawsuit contends. It said Krieger never intended to pay back the loan.

The lawsuit claims that in the years surrounding the restructuring and before Krieger stopped making the loan payments that precipitated Aspirity’s bankruptcy, Krieger transferred millions in cash from his businesses into personal bank accounts and to insiders.

According to the complaint: Krieger between June 2015 and July 2017 made a $1 million down payment on an oceanfront home in Port Townsend, Wash.; purchased a $295,000 diamond, and gave more than half a million dollars to one of his ex-wives.

It also said that Krieger transferred more than $948,000 to a holding company owned by an Aspirity board member and $918,000 to a longtime business associate.

The restructuring and other transfers were made with intent “to hinder, delay and defraud” Aspirity Financial and the holders of the bank note, the lawsuit charges.

“Krieger engaged in self-dealing transactions and otherwise breached fiduciary duties owed to Aspirity Financial” and its creditors, the suit said.

As part of a court-ordered financial examination, Krieger refused to answer questions related to the restructuring and other financial transactions. During a deposition, he asserted his Fifth Amendment right against self-incrimination more than 380 times, according to filings.

“The top attorney in the city says if you don’t plead the Fifth, I won’t represent you,” Krieger said. “What would you do? Think of the corner you’re backed into. I want to tell the truth.”

In court documents, Krieger called the accusations of fraud “baseless.”

“Mr. Krieger wishes to clear his name and resolve this bankruptcy case as quickly as possible,” Will Tansey, one of his attorneys, wrote in a separate filing. He said Krieger did not object to “the extremely broad” financial investigation and supplied 7,500 pages of documents.

“Armed with all of this information and despite Mr. Krieger’s willing cooperation, the trustee personally attacks Mr. Krieger and accuses him of interference with the process, demonstrating a willingness to distort misuse of this financial information,” the filing said.

Krieger, who won two national titles in college, was the subject of a Star Tribune investigation in 2017 that led to legal scrutiny. Investors filed an involuntary bankruptcy petition against Aspirity Holdings in March 2018, and several former employees have sued.

As part of divorce proceedings from his wife, Whitney, Krieger claimed he was broke. His Prior Lake home is being marketed on several websites for $2 million.