Former NSA contractor officer Jeffrey Sterling (reality winner) 25, in 2015 received three and half years in prison for leaking details of a secret mission to thwart Iran’s nuclear ambitions. Savannah Ga. (AP) Prosecutors say a Georgia woman who pleaded guilty to mailing a secret U.S. report to a news organization faces the “longest sentence” ever for a federal crime involving leaks to the media. while former CIA veteran John Kiriakou received 2 ½ years in prison in 2013 for leaking a covert officer’s identity to a reporter. Prosecutors noted their plea deal with Winner allowed the U.S. government to avoid disclosing secret information in a public courtroom. If Winner stood trial, they said, prosecutors would have been forced to reveal the classified report she leaked and have witnesses explain its contents. Authorities have never described the report Winner leaked or identified the news organization that received it.