In June 2009, Darrow was charged with extortion in a 2004 incident. Along with Gambino crime family soldier Joseph "Joey Boy" Orlando and associate Giovanni "Johnny" Monteleone, Darrow was accused of ordering the maiming of a man in Monticello, New York who owed money to a loan shark. Darrow and Orlando both pleaded guilty in federal court to these charges in February, 2011 in exchange for a sentence of up to 33 months, however Monteleone cooperated with the FBI. At sentencing, Darrow's attorney successfully argued that Darrow's 50+ year history of community Service, medical condition, and lack of prior Criminal history warranted a sentence of house arrest, followed by a period of probation. Orlando was sentenced to 51 months in prison and Borgese received six months of house arrest.