
KEY WEST, Fla. — Former Monroe County Information Technology Director Lisa Druckemiller, who served 18 months in state prison for stealing and selling county-owned iPhones and iPads, was arrested Sept. 18 on an alleged probation violation and remains jailed without bond pending a Sept. 30 hearing.
Monroe County booking records show Druckemiller was taken into custody Sept. 18.
The violation stems from her failure to pay all financial obligations associated with her criminal case, including court-ordered amounts imposed as part of her sentence.
The amount that landed her back in jail?
$623.
Druckemiller previously pleaded guilty to grand theft of more than $20,000 and dealing in stolen property after admitting she stole and sold 34 iPhones, 12 iPads and one other cellphone belonging to Monroe County. The equipment was valued at about $23,000.
Circuit Judge David Audlin sentenced her to 18 months in state prison followed by 13 years of probation and ordered her to pay $16,000 in restitution.
Druckemiller’s probation was later modified by Judge Mark Jones in 2018, waiving supervision costs that were in arrears and resetting the cost of supervision to $20 per month. He also gave her the opportunity to apply community service towards credit for the cost of supervision court fines.
At sentencing, Audlin called the case a breach of public trust and said Druckemiller would have received more than five years in prison had she not cooperated with investigators and voluntarily testified before the county grand jury.
Druckemiller had faced as much as 30 years in prison. Prosecutors had asked that she serve two years.
Her attorneys sought probation, arguing she had already lost her pension, health insurance and standing in the community.
During the original case, Druckemiller said County Administrator Roman Gastesi had started her down the path by allegedly giving her $200 and asking her to obtain iPhones for his sons. She said she complied because she feared losing her job.
Prosecutors countered that the theft and sale of county equipment extended far beyond Gastesi and county employees. Assistant State Attorney Mark Wilson told the court that 19 other people outside Gastesi received items and that witnesses told the grand jury Druckemiller had approached people about buying phones and other equipment from her.
Druckemiller ultimately accepted responsibility, telling the court she knew her actions were illegal and wrong.
Her current detention comes years into a probationary term that followed her prison sentence. Monroe County Clerk guidance says people on probation who are unable to pay court-ordered fines should contact their probation officer and warns that late payments can result in a bench warrant if the appropriate office is not notified. The Clerk separately directs defendants on probation to follow their restitution orders and probation officers’ payment instructions.
Druckemiller remains at the Monroe County Detention Center without bond and is scheduled to return to court Sept. 30 on the alleged probation violation.





