“We Had a Deal!”: When the Prosecutor Breaks a Promise (And Why Fixing It Can Be Dangerous)

By: John Guidry

It’s never easy for a defendant to stand before a judge for sentencing. In over 20 years of defending criminal cases, I’ve seen my fair share of judges reject a plea deal at the last minute. Sometimes, it’s a blessing. A few years ago, a judge rejected my client’s plea, we went to trial, and we won a Not Guilty. Unfortunately, most rejected pleas end in a worse position.

But is it fair that a defendant ends up with a worse sentence because the State lied? This is America, right? Let’s take a peek at a case involving a plea agreement gone wrong, and what can be done about it.

Did the prosecutor promise a recommendation but then ask for the maximum?

That is a breach of contract. Call John today at (407) 423-1117.

The Case: O’Berry v. State (The Broken Promise)

The Facts: Joshua O’Berry was charged with Burglary of a Dwelling with Assault/Battery. This is a First-Degree Felony punishable by Life in Prison.

• The Deal: To avoid trial, O’Berry entered an “Open Plea” to the bench. The State agreed to recommend 40 years in prison. (Yes, 40 years was the “good” offer).
• The Breach: At sentencing, the prosecutor didn’t recommend 40 years. Instead, he told the Judge: “The State is asking for the maximum [Life] in this case, Your Honor.”
• The Result: The Judge sentenced O’Berry to 50 years in prison.

The Argument: O’Berry’s attorney immediately objected, noting the 40-year agreement. The prosecutor backpedaled, admitting they had discussed 40 years, but the damage was done. The Judge dropped the hammer.

The Ruling: A Plea is a Contract

O’Berry appealed, arguing he should be allowed to withdraw his plea because the State lied. In O’Berry v. State, 114 So. 3d 1110 (Fla. 2d DCA 2013), the Appeals Court agreed that the State cheated.

• The Logic: A plea agreement is a Contract. If the defendant gives up his right to a trial based on a promise, the State must fulfill that promise.“When the State fails to honor a plea agreement… the violation is akin to a breach of contract for which the defendant is entitled to seek a remedy.”

The Remedy (The Catch-22): Here is the scary part. The Court did not automatically let O’Berry withdraw his plea. Instead, they ordered Specific Performance:

1. The case is sent back for Resentencing.
2. It must be before a Different Judge.
3. The State must recommend 40 years this time.

BUT… The new Judge is not bound by the recommendation. The new Judge can listen to the 40-year recommendation and still decide to sentence O’Berry to Life.

John’s 2026 Update: Negotiated Pleas vs. Open Pleas

Note: In 2013, O’Berry took a gamble on a recommendation. In 2026, we don’t gamble.

1. The Death of the “Recommendation” Plea Because of cases like O’Berry, smart defense attorneys in 2026 rarely accept a plea where the State only promises to “Recommend” a sentence.

• The Risk: Recommendations are non-binding. The Judge can ignore them.
• The Solution: We negotiate Rule 3.171 Plea Agreements where the Judge agrees to the specific sentence before the plea is entered. If the Judge agrees to 40 years, you get 40 years. If the Judge changes their mind later, you are legally entitled to withdraw the plea immediately.

2. Everything in Writing In O’Berry, there was confusion about whether the 40-year offer was “accepted” or just “discussed.”

• The 2026 Practice: We now use Digital Plea Colloquies. The terms are typed into the court system’s docket instantly. There is no “he said/she said” about what the offer was. If the prosecutor tries to change it at sentencing, we pull up the digital transcript on the spot.

3. Specific Performance is Still Risky If you win an appeal like O’Berry did, you get a “Do-Over” with a new Judge.

• The Warning: New Judges often resent having to clean up old cases. If the facts are bad (like a home invasion), the new Judge might look at the 40-year recommendation and say, “Thank you for the suggestion, Mr. Prosecutor, but I believe Life is appropriate.”
• The Strategy: Sometimes, it is safer to negotiate a specific term of years to resolve the breach rather than rolling the dice on a resentencing.

Get It Locked Down

A promise from a prosecutor is worth the paper it isn’t written on. If you are entering a plea to a serious charge, you need a guarantee, not a recommendation.

Call me at (407) 423-1117. Let’s get the Judge’s signature first.

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.