🎙️ Episode Summary
The Show’s Format
Former FBI agent Tom Simon and former con artist Matt Cox discuss crime from opposite perspectives. In the episode’s game, Tom presents 10 federal cases, and Matt tries to guess each defendant’s prison sentence. A guess earns a point if it is within 25% of the actual sentence.
Before the game, Tom shares an undercover story: while disguised for an FBI assignment, he was called out for wearing obviously fake glasses—not by his targets, but by a clown at the hotel. He stayed calm, brushed off the interruption, and continued the meeting without breaking cover.
The hosts also discuss how some people repeatedly return to prison, including people who violate supervised release and are eventually deemed unable to comply with supervision.
⚖️ The 10 Cases
| Defendant | Crime | Actual sentence |
|---|---|---|
| Tracy Smith | A Pittsburgh accountant on supervised release for an earlier embezzlement stole about $1.17 million from two companies. She committed the second theft while awaiting sentencing for the first. | 76 months |
| Braden Karony | The former SafeMoon CEO and co-conspirators allegedly claimed the cryptocurrency’s liquidity pools were locked, while retaining access and diverting funds. Karony took about $9 million, spent lavishly, and pleaded guilty to securities fraud, wire fraud, and money laundering. | 100 months |
| William Engel | A former attorney promised small-business owners multimillion-dollar loans, collected “good faith” deposits, and spent the money personally. Victims lost about $8.27 million. | 108 months |
| Matthew Bros | A steakhouse manager spent roughly $1 million on personal purchases using the company credit card, and impersonated the owner when questioned about missing tax money. | 21 months |
| Michael Minan | An employee of a nonprofit high-school sports and arts association made more than 1,100 unauthorized credit-card purchases over 13 years, totaling about $543,000. He concealed purchases with altered receipts. | 18 months |
| Abdullah Hajj Zada | At 17, he planned an ISIS-inspired attack on Election Day, obtaining two AK-style rifles and ammunition. He pleaded guilty and agreed to be deported to Afghanistan after serving his sentence. | 15 years |
| Michael Howser | A casino manager stole about $25 million over eight years and failed to report the income, creating an additional tax loss of roughly $8.2 million. | 70 months |
| Darren Lewis Payne | A 23-year-old convicted felon robbed a bank at gunpoint, taking about $9,175. Investigators linked him to the crime through surveillance, his truck, clothing, cash, and searches in his ChatGPT history for help planning a robbery. | 121 months |
| Bobby Leon Smith III | He ran a Medicare telemarketing scheme selling unnecessary medical equipment, using kickbacks and forged prescriptions. The operation billed Medicare about $61.5 million. He changed his plea after trial testimony and later fled before sentencing. | 150 months |
| Melvin Wiltshire | He robbed an Arkansas bank at gunpoint, taking about $23,850. He abandoned clothing, a weapon, and cash nearby, and DNA linked him to the evidence. | 114 months |
Matt finished with 4 points out of 10.
💡 Main Takeaways
- Fraud often depends on deception. Tom distinguishes a crypto “rug pull” from an illegal fraud: selling off one’s holdings is not necessarily fraud by itself, but falsely promising investors that withdrawals are impossible can turn the scheme into theft by deception.
- SafeMoon’s collapse drew major scrutiny. The hosts credit investigative YouTuber Coffeezilla with playing a significant role in exposing the alleged fraud and helping move the investigation forward.
- Controls matter. Several cases involved one trusted employee having too much access to company money with too little oversight.
- AI can help or hurt. The hosts describe using AI for research, marketing, document analysis, and organizing financial records. Payne’s case shows how searches for criminal advice can also become evidence.
- Prison sentences vary widely. The conversation considers the amount stolen, number of victims, criminal history, guilty pleas, and other case details when estimating punishment.
The episode closes with the hosts thanking viewers and encouraging them to subscribe to the Tom Simon and Matthew Cox podcast channel.
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