U.S. Bankruptcy Judge Robert J. Kressel issued an order on Wednesday demanding that Denny Hecker and his girlfriend, Christi Rowan, turn over insurance checks-totaling about $109,000-that allegedly belong to the bankruptcy estate.

Hecker had 24 hours to comply with the order, which also required him to provide an account of how the couple used the proceeds from the insurance checks and to turn over all property purchased with those funds to the trustee.

Hecker responded within the 24-hour window by providing a 30-page account of how he spent the funds-and why he's broke.

The list of expenses includes $18,000 in office rental payments, $4,300 paid to Lafayette Country Club, $2,750 spent at Manny's Steak House, $8,000 given to Rowan to cover TCF Bank overdraft fees, and $1,082 to cover DirecTV bills, among others.

Hecker “has no remaining funds from the liquidation of estate assets,” the document states. “He has nothing to turn over to the court.”

Randall Seaver, the trustee in Hecker's bankruptcy case, filed a complaint late last month alleging that Hecker and Rowan have collaborated to hide assets from the court.

According to the complaint, Hecker deposited an insurance check for $30,000 into an account at 21st Century Bank. After opening the account, the bank “became concerned,” froze the account, and returned the funds to Hecker. When Hecker received a cashier's check from the bank totaling $30,000 in June, he quickly cashed it.

The trustee later learned that Hecker and Rowan had used a cash-checking service and had cashed four checks from insurance policies in addition to the $30,000 check. The four checks totaled about $123,000, according to the complaint.

Judge Kressel's order states that the insurance checks are property of the bankruptcy estate, “and the defendants are wrongfully exercising dominion and control over” the ill-gotten funds. “It is also likely that defendants possess and control, or have already disposed of, additional property of the estate,” Kressel wrote.

Hecker is also accused by the government in a criminal case of defrauding lenders by forging documents to obtain more than $100 million in loans. He pleaded guilty last month to two criminal counts related to bankruptcy fraud and conspiracy.