“Buyer’s Remorse” in Prison: Why Withdrawing Your Plea Can Ruin Your Life

By: John Guidry

“Answered prayers cause more tears than those that go unanswered.” — Saint Teresa of Avila

Have you seen the new Chevy ads? Buy a Chevy, and if you don’t “love it,” you can return the car within 60 days. Some defendants here in Orlando assume that our court system has that same high level of customer service. But as you know—it doesn’t.

The Reality: When a plea is entered, there is rarely an opportunity to go back and undo it just because the deal wasn’t what you expected. However, you’d be surprised how many folks enter a plea involving prison time, only to spend their days in the library researching ways to undo it.

The Danger: Let’s say you are one of the lucky prisoners who convinces a Judge to undo your agreed-upon prison sentence. Now what? Now, you are back at square one. The deal is gone. The original charges are back. And the prosecutor is angry.

Are you thinking about withdrawing your plea?

Stop. Call John first at (407) 423-1117.

The Case: Ciambrone v. State (The 55-Year Mistake)

This nightmare scenario actually happened in Ciambrone v. State (Fla. 2d DCA 2012).

• The Original Deal: Mrs. Ciambrone was charged with First Degree Murder (Child Abuse resulting in death). She negotiated a plea deal to Second Degree Murder in exchange for 55 years.
  • Why take 55 years? Because it saved her from a Life Sentence.
• The Regret: Years later, she requested to withdraw her plea, arguing her attorney gave her bad advice about “gain time” (early release).
• The “Win”: In 2006, the Appeals Court granted her motion. She won! The plea was ripped up. She was free to go to trial.

The Consequence: In 2007, she went to trial.

• The Verdict: Guilty of First Degree Felony Murder.
• The Sentence: Life in Prison Without Parole.

The Final Appeal: She appealed again, asking for her old deal back. The Court denied it. The Appeals Court summed it up with a chilling observation:

“Prisoners who fantasize about a future court proceeding in which their motion to withdraw… results in their freedom should consider… Mrs. Ciambrone, whose motion to withdraw a plea to a lesser offense now makes it very likely that she will die in custody.”

The Lesson: Be Careful What You Wish For

Mrs. Ciambrone won the battle (withdrawing the plea) but lost the war (dying in prison). Before you file a Rule 3.170 Motion to Withdraw Plea, ask yourself:

1. Can the State prove the original, higher charge?
2. Is the prosecutor willing to seek the maximum? (Yes, they usually are).
3. Does the Judge remember that you wasted the Court’s time?

If you withdraw your plea, you don’t just get a “do-over” on the negotiation. You often get a one-way ticket to trial on the worst possible charges.

John’s 2026 Update: The Digital Trap & AI Risk

Note: In 2007, Ciambrone hoped the evidence had faded over time. In 2026, evidence never dies.

1. Digital Permanence (The “Cold Case” Problem) In the old days, defendants withdrew pleas hoping witnesses had moved away or forgotten the details.

• The 2026 Reality: Today, the evidence is digital. Body cam footage, text messages, and GPS data are stored forever in the Cloud.
• The Result: If you withdraw your plea 5 years later, the State’s case is just as strong as Day 1. The digital witness never forgets, never moves away, and never changes its story.

2. AI “Win Probability” Analytics Before we even consider withdrawing a plea, defense attorneys now use AI Legal Analytics.

• The Tool: We run your case through software that analyzes thousands of similar trials in your county.
• The Prediction: If the AI says, “Defendants with these charges have a 92% conviction rate at trial,” we show you that number. It stops “wishful thinking” dead in its tracks.

3. The “Trial Tax” is Automated State Attorney’s Offices now use automated case management.

• The Policy: If a defendant withdraws a negotiated plea, the system often automatically flags the case for “Maximum Statutory Penalty.” The offer is removed, and the computer ensures the new prosecutor knows not to offer a deal again.

Don’t Gamble with Your Life

For every Mrs. Ciambrone, there are 10 others who got better deals—but are you willing to bet your life on it? If you have buyer’s remorse, we need to analyze the risk before we pull the trigger.

Call me at (407) 423-1117. Let’s calculate the odds.

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.