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Timothy Toohey’s fall from power, a decade-long decline marked by tax evasion and embezzlement convictions, ended Monday with the former Democratic Party insider going to federal prison for a second time.

Toohey was sentenced to 33 months for his role in a controversial land deal by the Seneca Nation of Indians.

“I consider my life now a sinkhole of regret,” he told U.S. District Judge Richard J. Arcara.

The now-disgraced former lawyer admitted stealing $202,000 from the Senecas as part of their purchase of 250 acres of land that eventually became the Hickory Stick Golf Course in Lewiston.

As part of his plea deal with prosecutors, Toohey implicated Bergal Mitchell III, former vice chairman of the Seneca Gaming Corp., in the crime.

He claims he and Mitchell each shared in the profit from a sale that cost the Senecas $2.1 million even though only $1.2 million went to the sellers.

Toohey, of Lewiston, also said he and Mitchell tried to conceal their illegal activity from Seneca leaders.

“He cooperated early and often,” said Joel L. Daniels, Toohey’s defense lawyer. “And we are ready to continue cooperating. Whatever the government requires, we’re here.”

Prosecutors granted Toohey a break on his recommended sentence in return for what Assistant U.S. Attorney James P. Kennedy described in court papers as his “substantial assistance in the investigation and prosecution of other persons.”

The charges against Mitchell are still pending, and there’s the possibility that Toohey could receive another break depending how much more he cooperates.

He could, for example, be a key witness at Mitchell’s trial, now scheduled for June.

“They’re engineering this,” Paul Cambria, Mitchell’s defense lawyer, said of Toohey and the prosecution. “It’s obvious he has the ability to reduce his sentence if he says things that please the government."

From the very beginning, Toohey emerged as a key figure in the five-year investigation by the FBI and Internal Revenue Service.

It was Toohey who, as part of his plea deal, admitted skimming money from the $2.1 million that the Senecas agreed to pay for the property.

And it was Toohey who told prosecutors that his share was $202,000, while Mitchell got $248,000, and Mitchell’s wife, Rachel, got $90,000.

As part of his sentencing, Toohey was ordered to repay the $540,000 that he claims the three received from the land deal.

Several members of the Seneca Nation were in the courtroom Monday to watch what one of them called an end to one aspect of the land sale story – Toohey’s involvement – and the start of another, Mitchell’s trial next year.

“I’m glad to see part of the Hickory Stick investigation come to a close,” said Richard Nephew, chairman of the nation’s Legislative Council. “And I look forward to the upcoming conclusion of the rest of it.”

For Toohey, a decorated Vietnam War veteran and a Democrat who rose through the ranks to become parliamentarian of the Assembly, Monday’s sentencing marked a new low.

“He was broke,” Daniels told Arcara. “Didn’t have any money. Owed money. It’s an old story.”

Toohey’s sentencing was not his first appearance before Arcara.

In 2006, the judge sentenced him to a year in prison after he pleaded guilty to tax evasion.

“To be honest with you, I never thought I’d see him again,” Arcara told Daniels. “For some reason, this all went amiss.”

email: pfairbanks@buffnews.com