(Bloomberg News) The $35 million estate of Bradley H. Jack, the former Lehman Brothers Holdings Inc. managing director who was arrested twice for allegedly forging drug prescriptions, may be sold at a municipal auction after he failed to pay property taxes since July.

Jack owes $271,923 on his 20-acre (8-hectare), waterfront compound in Fairfield, Connecticut, according to town tax collector Stanley Gorzelany. It's the town's biggest overdue tax bill on a residence.

"He is the most delinquent taxpayer," Gorzelany said in a telephone interview.

Jack, 53, turned himself in and was charged March 9 with second-degree forgery for a November incident at a CVS pharmacy in which he faked the date on a doctor's prescription for a controlled substance, according to Capt. Sam Arciola of the Westport Police Department. Jack was released on $5,000 bond and has a March 21 court appearance.

In June, Jack was arrested after he allegedly tried to pass forged prescriptions for 12 pills of the painkiller Oxycontin and nine of Ritalin, a drug used to treat attention deficit disorder, Fairfield police said.

Jack had received treatment for cancer, had had a valid prescription in the past and had no prior criminal record, his attorney, Robert G. Golger, said in court in August. Golger didn't immediately return a call today seeking comment on the tax sale.

On the same day last week that Jack turned himself in, Fairfield placed his property at 1143 Sasco Hill Road on a list of delinquent homes to be included in a tax sale within the next four months, Gorzelany said. The sale date hasn't been set.

"We had been discussing a tax sale for weeks before that happened," Gorzelany said of Jack's most recent arrest. "It was just pure coincidence."

Pool, Tennis Court

Jack's property, which includes five buildings, a pool and a tennis court, is the most expensive in Fairfield, according to the tax collector's office, which places its market value at $34.6 million as of October 2010. His total annual tax bill is $543,847.48.

He bought the estate in 2001 for $24.45 million, according to the Fairfield Assessor's office.

Individuals who owe more than $50,000 in back taxes, regardless of how long they've been delinquent, will have their property subject to a tax lien sale, Gorzelany said, citing criteria set by the town of Fairfield.

If Jack doesn't pay the back taxes before the auction date, buyers will have the opportunity to acquire his property at a starting bid of $426,240 and unspecified legal fees associated with the sale, Gorzelany said. The starting bid includes quarterly taxes that will be due in April.

After a tax sale, delinquent taxpayers have six months to redeem their property by paying the back taxes to the town and paying the winning bidder up to 9 percent of their final bid, Gorzelany said.

Jack joined New York-based Lehman in 1984 and ran investment banking from 1996 to 2002, when he became co-chief operating officer with Joseph Gregory. In 2004, he was named to the office of the chairman with the responsibility of overseeing all of the firm's investment banking relationships.

He decided to retire from New York-based Lehman to pursue work in the nonprofit sector and spend time with his family, Richard Fuld, Lehman's chief executive officer at the time, said in June 2005. The company went bankrupt in September 2008.