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Press Release Two Men Sentenced to Jail in Connection with Multimillion-Dollar Sports Betting Operation

For immediate release:
10/03/2017
  • Office of Attorney General Maura Healey

Media Contact

Chloe Gotsis

BostonTwo leaders of a multimillion-dollar sports betting operation in the Boston and South Shore areas have pleaded guilty and been sentenced to jail for taking illegal bets from hundreds of gamblers across the state, Attorney General Maura Healey announced today.

John Woodman, age 45, of Braintree, pleaded guilty Thursday, Sept. 28 in Suffolk Superior Court to the charges of Money Laundering, Organizing and Promoting Illegal Gaming, Registering Bets, Using the Telephone to Register Bets, Delivery to and from a Person Engaged in Illegal Gaming and Conspiracy to Register Bets (one count each). Woodman was sentenced to one year in the House of Correction, followed by three years of probation and ordered him to pay a $50,000 fine. He was also ordered to forfeit more than $100,000 in proceeds from the illegal scheme.

Keefe Sheppeck, age 41, of Boston pleaded guilty on Monday, Sept. 25 in Suffolk Superior Court to the charges of Operating a Game or Gaming Device without a License, Money Laundering, Organizing and Promoting Illegal Gaming, Registering Bets, Using the Telephone to Register Bets, Delivery to and from a Person Engaged in Illegal Gaming and Conspiracy to Register Bets (one count each). Sheppeck was sentenced to two and a half years in the House of Correction, with the sentence suspended for a three-year period, and ordered to pay a $25,000 fine. Sheppeck previously agreed to forfeit a car and more than $35,000 in proceeds from the scheme.

“These men were the masterminds behind a major sports betting scheme that aggressively pursued debtors and utilized an offshore betting website to circumvent our state gambling laws,” said AG Healey. “This case is the result of our continued work with state and federal law enforcement partners to take down these organized criminal networks.”

According to authorities, Woodman maintained a network of more than 30 agents who took illegal bets from more than 700 bettors in Massachusetts. Sheppeck was a sub-agent, who also had his own agents under him. Some bettors owed more than $100,000 in debts during the time of this investigation. Bettors who owed money were pursued aggressively at work and home, resulting in at least two of them moving out of state. The agents provided bettors with accounts on an off-shore sports betting website called PerHead, which allowed them to register and track bets. Bettors utilized PerHead and its system to register their bets on professional and college football, basketball, baseball and hockey. The agents would then directly collect debts or pay winnings to the bettors in person.

Investigators seized $450,000 in cash, three guns, and six vehicles during the course of the investigation. Yearly profits of this operation exceeded $3 million, and from May 2014 to May 2015 about $6 million worth of bets were placed.

Woodman’s and Sheppeck’s charges were part of a 122-count indictment returned by a Statewide Grand Jury in November 2015 against a total of 35 individuals involved in the scheme. The charges were the result of an investigation by the AG’s Office and the Massachusetts State Police, with assistance from various federal, state, and local authorities.

The investigation began in August 2014 when the Massachusetts State Police Special Service Section’s Organized Crime Unit developed information about a statewide betting operation based out of East Boston and South Boston and began investigating the matter with the AG’s Gaming Enforcement Division.

The case was being prosecuted by Assistant Attorney General Patrick Hanley, Chief of AG Healey’s Gaming Enforcement Division, and Assistant Attorney General Kristyn Dusel, also of the AG’s Gaming Enforcement Division. The case was investigated by the State Police Special Service Section – Organized Crime Unit, the State Police Gaming Enforcement Unit assigned to the Attorney General’s Office, civilian investigators assigned to the Gaming Enforcement Division and the AG’s Digital Evidence Lab. The AG’s Office received support from the Massachusetts Gaming Commission. The AG’s Office received assistance from the State Police Technical Surveillance Unit, State Police Fusion Center, State Police Crime Scene Services Section, Alcoholic Beverage Control Commission, Department of Corrections, Boston Police, Quincy Police, the Federal Bureau of Investigation, Internal Revenue Service, U.S. Attorney’s Office, Nevada Gaming Control Board, and the Suffolk, Norfolk and Plymouth District Attorneys’ Offices.

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Media Contact

Office of Attorney General Maura Healey 

Attorney General Maura Healey is the chief lawyer and law enforcement officer of the Commonwealth of Massachusetts.

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