Gross was a U.S. international development professional. In December 2009 he was arrested while in Cuba working as a U.S. government subcontractor for the U.S. Agency for International Development (USAID) as part of a program funded under the 1996 Helms-Burton Act.
He was prosecuted in 2011 after being accused of crimes against the Cuban state for bringing satellite phones and computer equipment (to members of Cuba’s Jewish community) without the permit required under Cuban law.