Court records in San Joaquin County show Pirro plead "Guilty" or "No contest" to an array of charges over the years that date back to 1990, including theft, drugs, and assault.
Felix Boston, who owns the plane that crashed on Sunday, told CBS47 by phone on Monday that he's saddened to hear of Pirro's criminal history.
"Makes you angry that the court system doesn't take care of somebody like that," said Boston.
In November 1988, federal records show Pirro owned a Cessna 175 that was involved in an accident near the Tracy Airport. The report states Pirro was not licensed and did not have a medical certificate when he let the plane run out of gas not far from the airport. Pirro left the scene and did not file an accident report, the report stated.
"You know, I just lost a plane. You know, my partner and I lost a plane. That can be... They can be fixed. But if he would have caused loss of life for innocent people that would have been real sad," said Boston.
According to the California Department of Corrections, Pirro had been on parole since 2008.
Court records show Pirro was scheduled to be sentenced next month in San Joaquin County after pleading guilty to petty theft last year.
A spokesman for the National Transportation Safety Board says the agency should know within the next couple of days whether they'll launch their own investigation into Sunday's crash.