(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.