When Sheriff Jerry Demings who sat in office had sat down with us and had their attorney sit with us, they chose the grey shirt, they asked us not to wear blue.Jeremy Charles Dewitte
From 1998 until 2020 Jeremy Dewitte had several run-ins with law enforcement, in particular Orange County Sheriff’s Office.
During Jeremy’s first arrest in 1998 Kevin Beary was the sheriff of Orange County. Beary held the position from 1993 until 2009.
Kevin Beary was the son of a police chief and his brother Richard was also a police chief. Beary was appointed by former Governor Jeb Bush to co-chair the Florida Domestic Security Task Force.
In 2005 he was accused of corruption which resulted in an audit of his homeland security spending. In March of 2007 he was cleared by Florida Department of Law Enforcement (FDLE).
However on April 10, 2007 the Florida Commission on Ethics found probable cause to believe Berry violated Florida Ethics Laws.
In July 2009 Beary pled guilty to violating Florida Ethics Laws and was fined $20,000.
During this time period Jeremy Dewitte had a number of arrests. He was arrested twice for impersonating a police officer, twice for violating his probation, once for using a false name or being in unauthorized possession of an ID card, once for carrying a concealed weapon and once for lewd or lascivious battery on a minor.
Unsurprisingly, with legal issues of his own, Kevin Beary chose not to run for a fifth term as Orange County Sheriff.
In 2009 Jerry Demings won the election for the Democratic Party and he became the new sheriff of Orange County.
Jerry Demings was the police chief of Orlando Police Department for 21 years before he retired in 2002. He was the director of public safety for Orange County for six years until he became the sheriff on January 5, 2009.
Demings was re-elected in 2012 and again in 2016.
In 2012 Demings’ opponent Michael Greene made a complaint to FDLE.
Michael Greene was a retired New York police officer who claimed Demings conspired to reclassify 17 crimes as thefts instead of burglaries in an effort to make the crime rate look lower.
After an investigation an FDLE crime analyst stated some of the crimes should have been reported as burglaries but there wasn’t a conspiracy.
In 2019 Jeremy Dewitte told the media he sat down with the former sheriff and his attorney, Mark NeJame in 2015. Jeremy claimed he was being harassed by Orange County deputies.
In 2015 an Orange County Sheriff’s Office investigation was opened primarily to look into the business practices and legalities of Metro-State Special Services.
Reportedly the investigators were told not to look any further and no arrests were made. It is unclear why this order was given.
Ironically in 2015 Jerry Demings requested 500 body cameras for deputy sheriffs. He also became president of the Florida Sheriffs Association and he was criticized for not focusing on Orange County.
In August of 2018 Jerry Demings was elected Mayor of Orange County and Orlando Police Chief John Mina was his successor.
Jerry Demings was the sheriff of Orange County from 2009 until 2018. Jeremy Dewitte was released from Graceville prison facility in 2011.
Jeremy Dewitte was only arrested twice during those years, once for failure to register as a sex offender and again for violating his community control which was the punishment for this failure.
None of his arrests from 2011 until 2018 included police impersonation charges.
In a 2019 interview Jeremy stated his issues began when John Mina became sheriff. This was also the beginning of his impersonation arrests.
The arrests were the results of uncovered body camera footage from 2019, 2018 and 2017.
Witnesses told Orange County Sheriff’s Office that Jeremy was impersonating police officers in 2017 and 2018.
However it wasn’t investigated until September 2019 after Jeremy Dewitte’s Windermere arrest and after Jerry Demings left office.
Orange County Mayor Jerry Demings has never responded to Jeremy Dewitte’s 2019 media comments.
One of the greatest mysteries of this case is how Jeremy Dewitte could overtly display his alleged crimes and still stay under the radar of deputy sheriffs for nearly 10 years.