Searching the site for the inspector general of the DOT turns up several cases. Here are some that mention jail sentences. Note that the pilots typically had done more than just fly without a certificate.
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On Aug 5, Kenneth Wayne Leaming (a/k/a Keny Wayne), of Spanaway, WA, was sentenced in U.S. District Court in Tacoma, WA to 31 days jail time served and fined $1,000 for flying an airplane without a valid airman certificate. Leaming, who pled guilty to the charge in March 2005, has never held a pilot’s license, but operated his privately owned and unregistered Cessna aircraft on multiple occasions between 2002 and 2004 - a threat to aviation safety. The case was investigated with assistance from the Joint Terrorism Task Force, the Pierce County Sheriff’s Office, and the FAA.
Cornie Gene Lowe was ordered by a U.S District Court judge in Del Rio, TX, to pay a $5,000 fine and spend 6 months in jail for piloting a plane without a pilot’s license and lying to the FAA. Lowe flew as pilot-in-command from Del Rio to Ruidoso, NM, even though FAA revoked his pilot's license in December 2001. He also made false entries in airman logbooks as though he were a certified flight instructor and signed off biennial flight reviews of other pilots when he was not authorized to do so. Lowe co-owns Fontera Aviation, Inc, an aircraft fuel business at Del Rio International Airport in Texas. OIG conducted the investigation with assistance from FAA.
Donald Wilson was sentenced to a 15-month prison term by a U.S. District Court judge in Fort Lauderdale, FL, for piloting a plane without a legitimate airman certificate and flying a plane with an unapproved modification to its fuel system. Wilson used various fraudulent identities in order to obtain FAA licenses and falsely register an aircraft. He also modified a plane by installing fuel-tank systems without making the change according to FAA maintenance regulations.
On January 27, 2012, Colton Harris-Moore, 20, of Camano Island, Washington, was sentenced in U.S. District Court in Seattle, Washington. In June 2011, Harris-Moore pleaded guilty to bank burglary, interstate transportation of a stolen aircraft, interstate and foreign transportation of a stolen firearm, being a fugitive in possession of a firearm, piloting an aircraft without a valid airman's certificate, and interstate transportation of a stolen vessel. Mr. Harris-Moore's lengthy crime spree began in the Pacific Northwest and across the United States to Indiana, ending with a crash landing in the Bahamas. As a result, Mr. Harris-Moore was sentenced to 78 months in prison and three years of supervised release.
On February 24, 2012, Andrew Ryan Johnson of Virginia Beach, Virginia, pleaded guilty in U.S. District Court, Norfolk, Virginia, to one count of knowingly operating an aircraft subsequent to his Commercial Pilot Certificate having been revoked by the Federal Aviation Administration (FAA). Mr. Johnson was sentenced to twenty days in jail, assessed a $100 fine, and placed on probation for one year. While on probation, Mr. Johnson is not allowed to pilot an aircraft or conduct flight instruction.
Our investigation revealed that in 2009, Mr. Johnson's Commercial Pilot Certificate was suspended for 120 days for giving flight instruction in an aircraft that he knew was not airworthy. While under the 120 day suspension, Mr. Johnson flew as pilot-in-command on nine occasions. Because of these acts, in June 2011, the FAA revoked Johnson's pilot certificate. While Mr. Johnson's Commercial Pilot Certificate was revoked and his Flight Instructor Certificate was expired, he flew as the pilot-in-command and as a flight instructor on September 23 and September 27, 2011. While Mr. Johnson was giving flight instruction to the pilot during the September 27 flight, the aircraft's propeller struck the runway.
There was no estate to seek damages from.