PORTLAND, Maine — The former head of the Iron Horsemen Motorcycle Club, whose conviction for marijuana trafficking was overturned, was sentenced Monday in U.S. District Court to nearly 16 years in prison for his role in a cocaine distribution ring.

Richard Szpyt, 58, of Old Orchard Beach and Haverhill, Massachusetts, pleaded guilty June 2 to a drug conspiracy charge, according to information posted on the court system’s electronic case filing system.

By pleading guilty, Szpyt (pronounced zipt) admitted that in 2006 and 2007 he distributed at least 5 kilograms, about 11 pounds, of cocaine to customers in Maine using members of the motorcycle club to sell the drug in southern Maine.

Szpyt was sentenced Monday to 15 years and nine months in federal prison, to be followed by five years of supervised release.

He obtained the cocaine from Ramon Dellosantos, 47, of Haverhill, Massachusetts, according to court documents. Dellosantos pleaded guilty to the same drug conspiracy charge in May. He is scheduled to be sentenced Thursday in federal court in Portland.

Procedurally, the case took a long and winding road to its resolution. Szypt and Dellosantos were found guilty by a federal jury in May 2009 in Portland of conspiracy to traffic in marijuana and cocaine. Szypt was sentenced to life in prison. Dellosantos was ordered to serve 10 years behind bars.

However, their convictions in that case were reversed in August 2011 by the 1st U.S. Circuit Court of Appeals in Boston, and the men were released. In a 2-to-1 decision, the judges found insufficient evidence had been presented at trial to prove that Szypt and Dellosantos conspired to traffic both drugs.

Then, a federal jury in December 2011 indicted the pair on the conspiracy to distribute cocaine charge to which they eventually pleaded guilty. U.S. District Court Judge George Singal, the same jurist who sentenced Szypt on Monday, ruled in April 2013 that the new indictment violated the double jeopardy clause of the U.S. Constitution. In another 2-to-1 decision, the appellate court reversed that decision in January 2014, and the case went forward.

Both criminal defense attorney Leonard Sharon of Auburn and Assistant U.S. Attorney Dan Perry, who prosecuted the case, said after Monday’s sentencing that they have never handled a case with a similar procedural history.

Szypt faced between 10 years and life in prison because of the amount of cocaine he distributed. Under the federal sentencing guidelines, Dellosantos faces between 57 months and 71 months in prison.

Perry recommended the sentence the judge imposed. Sharon urged Singal to impose a 10-to-12-year sentence because of Szypt’s health issues that include a recent heart attack and diabetes.

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