Prosecutors relied on e-mail messages associated with work on behalf of the Mashpee Wampanoag to show that Ring provided tickets to sporting events and pricey meals to Robert E. Coughlin, the former Deputy Chief of Staff, Criminal Division, of the United States Department of Justice. He pleaded guilty in April 2008, saying he had accepted meals, concert tickets and luxury seats at Redskins and Wizards games from Ring. In return Coughlin helped secure a $16.3 million grant for the Mississippi Band of Choctaw Indians, whom Ring and Abramoff represented. Coughlin also helped students attending a school run by Abramoff quickly clear immigration hurdles. Court documents also asserted that Ring had provided gifts for Ann Copland, who was senior staff for Republican senator Thad Cochran. E-mails from Ring were subsequently part of the documents submitted when Copland pleaded guilty in March 2009.