It began with one inmate teaching another how to fabricate the legal paperwork, authorities say.
Investigators say the ringleader was 48-year-old Nydeed Nashaddai of Pinellas County.
From inside the Franklin Correctional Institution in North Carrabelle in Florida's Panhandle, Nashaddai trained inmates how to create the legal-looking documents with bogus signatures of prosecutors and judges, CNN quoted Gretl Plessinger, a spokeswoman for the state Department of Law Enforcement as saying.
Nashaddai used a similar technique in 2009 to walk away from the Pinellas County Jail before authorities figured out the scheme and recaptured him a day later, according to prison records.
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Charles Walker and Joseph Jenkins, both 34, had been serving life terms without parole for unrelated killings at Franklin Correctional Institution when they allegedly escaped.
Jenkins walked out September 27, while Walker left October 8. Both used legal-looking documents with bogus reproductions of several key players' signatures, including those of the Orlando-area state attorney and Judge Belvin Perry, plus the seal of the Orange County clerk of court's office.
Both men were recaptured in late October.
Neither Plessinger nor Bailey said whether investigators believe Nashaddai taught the two men directly. He is no longer housed at Franklin Correctional, Plessinger said.