ORLANDO, Fla. – Former Orlando Commissioner Regina Hill was arrested in March on charges including the exploitation of an elderly person, among others.
Now, public records have revealed that Hill is under federal investigation related to that case.
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The former District 5 city commissioner is accused of exploiting a 96-year-old woman and taking over $100,000 from her, state investigators have reported.
As the investigation into this case continues, here’s a look into the controversies that Hill has previously been tied to:
1989 - 2013 — PRIOR ARRESTS
Hill was arrested at least 21 times on a variety of charges, several of which were drug-related.
However, many of those charges were ultimately either dropped or the adjudication was withheld, court records show.
In 2000, she was arrested on a misdemeanor charge of disorderly conduct by the Orange County Sheriff’s Office. She later pleaded guilty to the charge, being sentenced to 179 days of supervised probation and 50 hours of community service.
In 2005, she was arrested on a charge of marijuana possession, for which she was sentenced to six months probation.
APRIL 2014 — ELECTIONS
Hill faced off against Juan Lynum — son of the former City Commissioner Daisy Lynum — in an election for the District 5 seat.
During the election, Juan Lynum received 36 more votes than Hill.
However, neither candidate received more than 50% of the votes, so the race went to a runoff election.
Days after the election, Juan Lynum came under investigation by the Florida Department of Law Enforcement as part of a fraud case. FDLE agents said they were looking into accusations that Juan Lynum lived outside of District 5.
MAY 2014 — ELECTIONS
Hill won her race against competitor Juan Lynum, earning over 54% of the vote in the runoff election.
Despite being attacked as a “career criminal” by her opponents, Hill acknowledged her history, but she said that what mattered was what she planned to do next.
“Sure I have had some issues in my past, but that has built integrity, that has built strength, that has built fortitude, that has built compassion, and the people have connected to that because I have walked in many of their shoes,” she said.
While she had no prior experience as an elected official, Hill told News 6 back then that she was focused on bringing jobs to her district.
AUGUST 2014 — AIDE ARRESTED
One of Hill’s aides, Cara Reaves, was arrested at a movie theater on charges of disorderly intoxication, trespassing and battery on a law enforcement officer.
In an arrest affidavit, police said Reaves had been shouting at the Plaza Cinema Café while smelling of alcohol, prompting an officer to ask her to stop.
While ordering refreshments, Reaves continued speaking loudly and argued with other guests, causing a manager to ask her to leave, though she ignored the manager, the affidavit shows.
Police said that while placing her under arrest, she continually shouted, “Oh, I’m sorry I’m black,” and court records show she scratched an officer on the arm.
However, the disorderly conduct charge was later dropped, and despite pleading no contest to the other two charges, adjudication was withheld. Reaves denied drinking the night of her arrest.
Despite the arrest of one of her top aides, Hill told News 6 that she was not connected to the incident.
“I’m neutral in this. It’s not a Regina Hill situation or a District 5 situation,” she said. “Ms. Reaves was on her personal time, and this is a journey Cara Reaves is going to go through not as the aide of Regina Hill.”
JULY 2015 — HOME RAIDED
A home owned by Hill was raided by Orange County deputies, leading to five arrests — including Hill’s son, 27-year-old Rakeem Hill, who was charged with the following:
- trafficking in methamphetamine
- possession of a firearm by a convicted felon
- possession of ammunition by a convicted felon
- possession of a firearm during the commission of a felony
- possession of cannabis.
Illicit drugs and at least one stolen gun were found inside the home, according to investigators at the time. However, Regina Hill was not at the home when the raid happened.
Around a week later, Regina Hill said she had been unfairly scrutinized for the incident.
“It’s not fair. I’ve been a hard-working woman and a mother for 27 years, and a nurse for 23 years. I have reports for 24 years. I am trying to serve my community,” Hill told News 6.
The charges against Rakeem Hill were dropped by prosecutors just a couple of months later, court records show.
APRIL 2017 — ONLINE VIDEO
A video posted online by Regina Hill sparked controversy after it led viewers to believe she was under the influence of drugs or alcohol.
“Power to the people, uh, we’re back,” Hill said in the video. “Actually, I’m not all that cohesive...”
[WATCH NEWS 6′S PREVIOUS COVERAGE BY CLICKING IN THE MEDIA PLAYER BELOW]
The commissioner later said in a statement that she “adamantly” denied the use of drugs. She said the video doesn’t show a commissioner high on drugs — it shows a mother in grief.
According to Tallahassee police, Hill’s 24-year old daughter, Arvonni DeBose, died under suspicious circumstances death in August 2015.
“The video depicts a mother who is overcome dealing with the loss of her daughter,” the statement reads.
Hill had been using video diaries to cope with the grief, the statement continued. It also said the video shared on social media was a personal video that she did not authorize anyone to release.
AUGUST 2017 — HOTEL INCIDENT
Regina Hill was found unresponsive on the floor in the DoubleTree Hotel penthouse, prompting hotel staff to call for emergency services.
An Orlando firefighter — Joshua Granada — responded to the distress call, though he didn’t initially realize that the woman was Regina Hill.
After EMT first responders revived Hill, she reportedly began shouting and making “accusatory remarks.”
“It was cursing, cursing, cursing. ‘I hate you, you’re trying to get me in trouble,’” Granada later told News 6. “‘I hate all of you firemen,’ and that’s what I heard, and I swear to you, I still didn’t know who she was.”
According to Granada, the hotel room looked like the aftermath of a “college rager,” with empty liquor bottles strewn about and the room reeking of cigarettes.
He also explained that Hill yelled out, “Stop touching me... All of you are trying to hurt me, you are all trying to do things.”
Due to Hill’s alleged accusations, Granada said he recorded a 30-second audio clip for his and his team’s safety.
NOVEMBER 2017 — COMPLAINT FILED
A complaint was filed against Hill, which alleged that she lived in a low-income apartment complex despite making over $60,000 per year in her role as a commissioner.
The complaint — filed by a family member of one of Hill’s political rivals — stated that Hill lived at the Landing at Timberleaf Apartments, which required residents to make $39,000 or less per year.
That complaint included a copy of the lease Hill submitted as part of her election paperwork, where it showed she paid $644 per month for rent, but her name didn’t appear anywhere on the lease.
Instead, the lease was accompanied by a notarized letter from another woman, which read, “Hill has resided with me since December of 2015 after her daughter’s death.”
Hill later responded to news about the complaint, calling it a “smear campaign.”
“I am working for the residents of Orlando, and that’s all I have to say about this,” she said.
NOVEMBER 2017 — FIREFIGHTER FIRED
Granada was fired from his position as a firefighter over the 30-second recording — since deleted — which was played in front of a few colleagues.
City records show that this was considered a breach of Hill’s privacy, hence why Granada was terminated.
The firefighters’ labor union held a press conference after the incident, saying it was a “wrongful termination.”
Hill later announced that she wanted to press charges against Granada.
“We also must be concerned that a firefighter who is violating patient’s privacy and their rights when they are most vulnerable,” Hill said. “Sadly, at this point, my privacy has been destroyed.”
MARCH 2018 — SON ARRESTED AGAIN
Hill’s son, Rakeem Hill, was arrested again after deputies accused him of fleeing a traffic stop and attacking law enforcement.
According to the Orange County Sheriff’s Office, Rakeem Hill had been spotted driving over 100 mph and swerving between lanes early in the morning.
After a deputy followed him to a parking lot, Rakeem Hill then backed his BMW into the deputy’s patrol vehicle, causing the deputy to draw his firearm and tell Rakeem Hill to get on the ground, investigators reported.
Court records show that Rakeem Hill then fled on foot, though after a chase and a short struggle, he was ultimately arrested. Marijuana was also found in the BMW, deputies said.
Rakeem Hill was eventually found guilty of resisting arrest with violence, though his charges of petit theft and battery on a law enforcement officer were dropped. He was sentenced to 18 months probation.
DECEMBER 2018 — FIREFIGHTER FACES CHARGES
Following his termination in 2017, Grenada was charged with unlawful interception of wire or oral communication, and willful disclosure of an unlawful interception of a wire or oral communication.
OCTOBER 2019 — FIREFIGHTER REINSTATED
After an extensive investigation, a federal mediator ruled that Granada shouldn’t have been terminated for the incident in August 2017.
While the mediator said a 240-hour suspension was appropriate, being fired was not, so Granada was reinstated with back pay.
However, Granada was ordered to pre-trial diversion due to his charges, but the charges would be dropped if the program was completed in six months.
Hill told News 6 that the ruling was “like a double slap in the face.”
“He betrayed the trust of all of our citizens when he illegally recorded myself on one of the calls for medical attention,” she said.
THE CURRENT CASE
After several years without a major public controversy, Hill once again came under scrutiny earlier this year when she was accused of exploiting an elderly woman.
According to court documents uncovered by News 6, the FDLE is investigating whether Hill established a power of attorney over a 96-year-old woman and secured a mortgage for a home in the Lake Man estates area of Orlando — without the elderly woman’s knowledge.
Investigators said they believe that Hill’s son and his girlfriend lived in the home while Hill lived in a separate house in the Washington Shores neighborhood.
That home once belonged to the elderly woman’s parents, but Hill wasn’t paying rent, the documents show.
According to the court records, Hill also used more than $100,000 of the woman’s cash and credit cards to buy perfume, clothing, IV vitamins, a facelift, a trip to Miami, dental surgery and car insurance.
In March, Hill was arrested on the following charges:
- Exploitation of the elderly/disabled
- Impersonation
- Scheme to defraud
- Mortgage fraud
“What we can speak about and what we know from the interviews and what we’re allowed to say today is that the victim in this case was not aware of how much she had signed over to Commissioner Hill,” said FDLE Orlando Special Agent John Vecchio at the time.
Vecchio also said that while the evidence shows Hill met the victim through her work as Orlando city commissioner, none of the charges against her involved her office.
“The charges today have to do with her acting as a citizen, not in her official capacity,” Vecchio said. “So we need to stay focused on these crimes. She is charged because of what she did as a person.”
An investigative report obtained by News 6 on Tuesday revealed that Hill is under federal investigation, as well.
According to the report, Hill had hired four people to care for the elderly woman, but none of them was affiliated with a health care agency. The report also states that one of them had a criminal history for illicit drug possession, aggravated assault, battery and other charges.
In addition, federal investigators said they conducted surveillance on 3411 Lewis Court, where Hill was suspected to be living. Agents determined she was living at that address, which is located in Orlando’s District 6 — not District 5, which she was elected to represent.
Shortly after her arrest, Hill bonded out of jail on $40,000. She later provided the following statement:
It’s unfortunate that I have been thrust into these circumstances with these allegations. Unfortunate not just for me but for (the 96-year-old woman), whom I’ve loved and cared for like my own family. I trust in God above all things, and I trust in the process. After ten years of service for the City of Orlando, I’ve illustrated my love and compassion for my constituents, my city, and my family. I know the truth; I know I’m entitled to due process, in which I trust, and I will await my day in court to prove my innocence.
Regina Hill
Days afterward, Gov. Ron DeSantis suspended Hill from her position, leading to a heated special election for her seat. Ultimately, Shaniqua Rose was voted in to take her place.
Hill’s criminal trial is slated to begin in September.
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