“What Are My Chances?”: Why You Should Never Trust the Odds (Or the Experts)

By: John Guidry

Every 23 seconds, an attorney is asked: “What are my chances of winning?” Some attorneys play along. Especially if it’s a slow month, they throw out a number like, “You have a 90% chance.”

• The Business: Confidence sells. The lawyer with the highest percentage usually gets the case.
• The Truth: After 23 years of defending criminal cases (my web people love statements that brag about decades of practice), I am here to tell you that such numbers are pulled out of thin air.

But attorneys aren’t the only ones guilty of this. Financial advisers and scientists are just as bad. To understand why, I turned to my Kindle highlights from Fooled by Randomness by Nassim Taleb. This book explains why the question “What are my chances?” is almost impossible to answer accurately.

Are you relying on a “guaranteed” outcome?

Don’t bet your freedom on a percentage. Call John today at (407) 423-1117.

Doctors Are Bad With Numbers

What happens when thousands of patients are told they have a disease they don’t actually have?

• The Scenario: A test is 95% accurate (5% false positive rate). The disease strikes 1 in 1,000 people.
• The Result: A patient tests positive. What are the odds they actually have the disease?

The Doctor’s Answer: Most doctors say 95%, simply looking at the test’s accuracy.

The Real Answer: The patient only has a 2% chance of having the disease.

• The Math: Out of 1,000 people, only 1 has the disease. But the test (with a 5% error rate) will flag 50 healthy people as “positive.”
• The Reality: If you test positive, you are likely one of the 50 false alarms, not the 1 sick person. Thousands of people are terrified unnecessarily because experts can’t do basic math.

The “Dying on the Table” Fallacy

Let’s say a surgery has a 99% survival rate. What would you say to a doctor who tells you:

“So far we have operated on 99 patients with great success; you are our 100th, hence you have a 100% probability of dying on the table.”

Conditional Life Expectancy: This highlights the confusion between “unconditional” and “conditional” probability.

• At Birth: Your life expectancy might be 73.
• At 73: If you are still alive, your expectancy isn’t 0. It increases. By not dying, you have “taken the spot” of others in the statistics. Even a 100-year-old has a positive life expectancy.

Financial Noise: Mistaking Luck for Skill

People strive to attach meaning to numbers that represent nothing but noise.

• The Headline: “Dow is up 1.03 on lower interest rates.”
• The Reality: A move of 1.03 is less than 0.01%. It is irrelevant. It is noise.

The Lesson:

“Unless something moves by more than its usual daily percentage change, the event is deemed to be noise… A 7% move can be several billion times more relevant than a 1% move!”

Journalists (and lawyers) are paid to provide explanations, so they invent reasons for things that are purely random. We cannot instinctively understand the non-linear nature of probability, so we let them fool us.

John’s 2026 Update: AI Win Rates & The “Digital Crystal Ball”

Note: In the past, lawyers pulled percentages out of thin air. In 2026, we pull them out of a computer.

1. The “AI Prediction” Scam In 2026, clients often use apps like Pre/Dicta or LexMachina to analyze their judge.

• The Pitch: “This AI says Judge Smith grants Motions to Dismiss 85% of the time!”
• The Flaw: Just like the doctors in Taleb’s book, these apps ignore the “False Positives.” The AI only sees published written orders. It doesn’t see the thousands of cases where the Judge denied the motion verbally in court. The data is incomplete, making the “85%” figure statistically worthless.

2. Algorithmic Sentencing (The New “Doctor” Problem) Courts now use AI Risk Assessments (like COMPAS 2.0) to predict if you will re-offend.

• The Math: The AI sees that you share traits with past offenders (zip code, age, history) and gives you a “High Risk” score.
• The Reality: This is the “Medical Test” error all over again. Just because 5% of people in your demographic re-offend doesn’t mean you will. But judges blindly trust the “High Risk” label just like doctors trusted the “95% Accurate” test.

3. Causation vs. Correlation Taleb warned that correlation (Hospital A has more boys than Hospital B) doesn’t prove causation.

• The 2026 Trap: Prosecutors use AI to find “correlations” in your behavior. “People who drive this route at 2 AM are 90% likely to be drug couriers.”
• The Defense: We have to fight to show that driving home from a late shift is correlation, not cause for a traffic stop.

Don’t Be Fooled

Whether it’s a doctor, a broker, or a lawyer with a shiny iPad, be wary of anyone giving you a specific percentage. The only number that matters is Zero (the number of convictions we want on your record).

Call me at (407) 423-1117. Let’s ignore the noise and fight the case.

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.