Can the Government Send You to Prison for Being Homeless in Orlando?

By: John Guidry

Have you ever seen a fist fight live? I hate violence—watching raw aggression is painful. But do you know what’s worse than the fight itself? It’s what happens to the guy who gets knocked down. Usually, the fight doesn’t just stop. The guy on the ground becomes the target of kicks to the head and body. We all know the cliché: you shouldn’t kick a man while he’s down.

Unfortunately, in the Florida justice system, kicking someone while they’re down is a standard operating procedure. I’ve seen it happen to clients in Orange and Seminole County more times than I can count. Today, we’re looking at a “beat down” taken by a woman named Ms. Charles at the hands of her probation officer, a prosecutor, and a judge who handed out a sentence that would make a UFC fighter wince.

Ms. Charles lived in one of those weekly motels—the kind of place where people are exactly one dollar away from homelessness. When the rent came due and she didn’t have it, she was evicted. Suddenly, she was homeless with two young children and no money. As I often say, many prison terms in Florida start exactly this way.

Facing a Violation of Probation (VOP) in Orlando? If the system is trying to kick you while you’re down, you need a defense that fights back. Call John Guidry at (407) 423-1117 today.

The Legal Breakdown: The Battle for “Willfulness”

The case of Charles v. State, 2016 Fla.App. LEXIS 16217 (Fla. 4th DCA 2016), is a perfect example of why the “typical script” of a probation violation is often a failure of proof. Ms. Charles was on probation and required to attend drug treatment and get permission before changing her residence. Here is how the “kicking” started:

• Strike One: Ms. Charles showed up to her drug treatment class with her two kids because she had no childcare. The facility refused her entry.
• Strike Two: She found a babysitter for the next class, but the sitter made her five minutes late. The facility denied her entry again and terminated her from the program.
• The Arrest: When she honestly updated her probation officer about being homeless and terminated from treatment, the PO put her in handcuffs.
• The Sentence: The judge sentenced her to 40.5 months in prison for these technical violations.
• The Reversal: The appellate court overturned the conviction. They ruled that for a VOP to stand, the violation must be willful.

The court noted that Ms. Charles made “reasonable efforts” to attend her sessions but was “thwarted by her childcare issues.” Furthermore, regarding her failure to report a change of address, the court cited Williams v. State, 896 So. 2d 805, holding that when a probationer is displaced and made temporarily homeless, a failure to get prior permission cannot be considered a willful violation.

John’s Takeaways

• Willfulness is the Key: If you made a reasonable effort to comply but were stopped by circumstances outside your control—like homelessness or childcare—the violation is NOT willful.
• Homelessness is Not a Crime: Florida law recognizes that if you are evicted and have nowhere to go, you haven’t “absconded” or intentionally changed your address to hide from the State.
• Reasonable Effort Defense: As shown in the Charles case, being five minutes late due to a babysitter is a “de minimis” issue that does not justify a 40.5-month prison sentence.
• Judicial Overreach: It is “insane” that a prosecutor and a judge would see a homeless mother of two and decide that the best “proper sentence” is three years in the Department of Corrections.
• The Cost of “Kicking”: Beyond the moral outrage, it costs Florida taxpayers tens of thousands of dollars to imprison a mother for technicality, while her children are left without a parent.

It’s “sad but true” that many government officials forget the basic command of “loving your neighbor” when they clock into the courthouse. They treat a struggling citizen like a criminal for being poor. Whether you are in Orange, Seminole, Osceola, Lake, Brevard, or Volusia County, you have rights that protect you from being punished for your bad luck.

I’ve been defending the citizens of Central Florida since 1993. If your probation officer is trying to turn your struggle into a prison sentence, give me a call. Let’s show the court that your actions weren’t a willful defiance of the law, but a reasonable attempt to survive.

Facing a VOP? Call John at (407) 423-1117.

About John Guidry II

John Guidry II is a seasoned criminal defense attorney and founder of the Law Firm of John P. Guidry II, P.A., located in downtown Orlando next to the Orange County Courthouse, where he has practiced for over 30 years. With more than three decades of experience defending clients throughout Central Florida since 1993, Guidry has successfully defended thousands of cases in Orange, Seminole, Osceola, Brevard, Lake, and Volusia counties. He has built a reputation for his strategic approach to criminal defense, focusing on pretrial motions and case dismissals rather than jury trials.

Guidry earned both his Juris Doctorate and Master of Business Administration from St. Louis University in 1993. He is a member of the Florida Bar and the Florida Association of Criminal Defense Lawyers. His practice encompasses the full spectrum of Florida state criminal charges, with a particular emphasis on achieving favorable outcomes through thorough pretrial preparation and motion practice.

Beyond the courtroom, Guidry is a prolific legal educator who has authored over 400 articles on criminal defense topics. He shares his legal expertise through his popular YouTube channel, Instagram, and TikTok accounts, where he has built a substantial following of people eager to learn about the law. His educational content breaks down complex legal concepts into accessible information for the general public.

When not practicing law, Guidry enjoys tennis and pickleball, and loves to travel. Drawing from his background as a former recording studio owner and music video producer in the Orlando area, he brings a creative perspective to his legal practice and continues to apply his passion for video production to his educational content.