Five Alabamians pleaded guilty earlier this week in federal court for their roles in a multi-million-dollar offshore sports-betting operation that stiffed the IRS of nearly $20 million in taxes, prosecutors announced Wednesday.

The Alabama residents were among 10 defendants who pleaded guilty to conspiring to operate an illegal gambling business and to their participation in a money laundering conspiracy.

According to the plea agreements, 53-year-old Birmingham resident Timothy J. Pughsley began operating a bookmaking organization at least 17 years ago that later became known as “Red44.”

Red44’s bookmaking and betting activities occurred via an offshore server in Costa Rica. The operation, prosecutors said, accepted more than $2 billion in bets.

Pughsley pleaded guilty before U.S. District Judge Madeline Haikala in Birmingham to conspiring to operate an illegal gambling business and to his participation in the money laundering conspiracy.

Along with Pughsley, the other Alabama residents who pleaded guilty to those charges were:

• Nathan Burdette, 39, of Birmingham
• Christopher Burdette, 32, of Chelsea
• Thomas Zito, 59, of Vestavia Hills

Jonathan Lind, 46, of Birmingham, pleaded guilty to consipiring to operate an illegal gambling business.

All of the defendants were senior agents within Red44 and agreed to pay excise taxes totaling more than $19 million to the IRS to satisfy outstanding income tax obligations.

“These guilty pleas are the end result of years of hard work by members of federal and state law enforcement agencies to enforce our nation’s gambling and tax laws,” said Prim Escalona, U.S. attorney for the Northern District of Alabama.

“The defendants illegally accepted millions of dollars in wagers and lived lavishly while avoiding their excise tax obligations,” Escalona continued. “This office will diligently pursue those who enrich themselves in violation of the law.”

Five others from outside Alabama pleaded guilty in the case: Gary Rapp, 46, of Lakeland, Tennessee; Mark Giaquinto, 52, of Upton, Massachusetts; Matthew Voorhees, 49, of Englewood, Colorado; David Richards, 39, of Las Vegas, Nevada; and Joshua Gentrup, 38, of Athens, Georgia.

Demetrius Hardeman, IRS special agent in charge with the IRS Criminal Investigation’s Atlanta field office, said excise tax evasion and illegal sports gambling “are not victimless crimes.

“Money obtained from illegal gambling operations is often used to finance other criminal activities,” he said. “IRS-CI special agents are skilled at following the money to investigate and expose these illegal organizations, who will be held accountable. Thank you to our local, state and federal partners who assisted in this investigation.”

IRS-Criminal Investigation and Homeland Security Investigations investigated the case, with help from the Vestavia Hills Police Department, Shelby County Sheriff’s Office, Alabama Department of Revenue and the FBI.

Assistant U.S. Attorneys Catherine Crosby, Kristen Osborne and Ryan Rummage are prosecuting the case.