🎥 Episode Summary: Tom Simon and Matthew Cox Show
Tom Simon, a former FBI special agent and current private investigator, and Matthew Cox, a former con man and inmate turned true-crime writer and podcaster, play “Guess the Sentence.” Simon describes federal cases, and Cox guesses the prison sentence; a guess counts if it is within 25% of the actual term. The episode ends with Cox scoring 4 out of 11.
🔎 Private Investigator Story
Simon recounts a custody-related investigation from early in his private-investigation career:
- A father hired him to locate his ex-wife and their child after she moved across the country with the child, apparently without allegations of abuse.
- Simon found the child’s school and tried to observe the pickup, but got trapped in the school’s long car line—and briefly had two unrelated children get into his vehicle.
- He eventually watched cars leaving from across the street, identified the mother’s car, followed her home, and provided the address to the father’s lawyer.
- Simon says surveillance work is often tedious and poorly paid: he estimates the average U.S. private investigator earns about $55,000–$60,000 a year. He now refers surveillance assignments to other investigators and notes that newer cameras can use AI to describe activity.
⚖️ Sentencing Game Cases
| Case | Crime and key facts | Actual sentence | Cox’s guess |
|---|---|---|---|
| Suliana Caldwell | Fresno Arts Council operations manager stole about $1.8 million through unauthorized transfers, hiding them with falsified financial reports. She spent much of the money at casinos. | 33 months | 18 months |
| Julia Roberts and Vicki Robinson | Two county-court accounting employees in Kansas stole about $980,000. Roberts was the supervisor; Robinson was her subordinate. Both pleaded guilty. | Roberts: 41 months; Robinson: 27 months | 18 months and 12 months |
| Manfred Gruber | Italian arms-industry executive helped route about $540,000 of U.S. ammunition through Kyrgyzstan to Russia, violating export controls. | 18 months | 36 months |
| Hector Rodriguez | Texas jailer sexually assaulted two incarcerated women. The women reported him to the FBI, and he admitted the conduct during questioning. | 20 years | 25 years — within the show’s range |
| Oasis Chowry | Queens resident pledged support to ISIS and planned a mass stabbing attack, scouting locations and ordering equipment. He was arrested before any attack occurred. | 9 years, plus 15 years of supervised release | 25 years |
| Flazelle Beasley | A 73-year-old serial robber targeted two banks, two credit unions, and a taco shop. A GPS tracker in a bank’s money pack led police to him on a public bus. | 17 years, 6 months | 15 years — within the show’s range |
| Christopher Dutton | Used IRS paperwork to redirect two corporations’ tax refunds—one worth $32 million—to himself. He tried to deposit the checks at Morgan Stanley and was convicted at a bench trial. | 3 years | 15 years; during the discussion, Cox also floated a much lower estimate |
| Buffy Redfish | Diverted about $4.7 million from a tribal employment-rights office over seven years, splitting the money with a co-conspirator. She was convicted at trial. | 78 months | 96 months — within the show’s range |
| Charity Felch | Stole about $386,000 from a small electrical contractor, including through fraudulent paychecks and personal use of company accounts. The theft nearly ruined the business; the judge also cited her lies to pretrial services. | 111 months | 84 months — within the show’s range |
| Nikolai Golsev | Canadian national who routed more than $7 million in U.S. electronic components through foreign front companies to sanctioned Russian entities. Some components were later found in Russian military equipment. | 40 months | 60 months |
💬 Other Discussion Highlights
- War Dogs: Cox says he served time with Efraim Diveroli, played by Jonah Hill, and co-wrote Diveroli’s memoir. They discuss how the arms deals involved paperwork that misrepresented where ammunition originated. Cox says Diveroli was initially expected to receive four years but ultimately served six after violating pretrial release conditions.
- Prison misconduct: Cox describes sexual relationships between some female inmates and corrections staff at a women’s camp, including contraband being brought in. He distinguishes those accounts from the assault case presented in the game, where the victims described coercion and force.
- Sentencing debate: Simon and Cox discuss how judges, districts, criminal histories, plea decisions, harm to victims, and whether a defendant goes to trial can affect sentences. Simon stresses that local stereotypes about lenient or harsh states may not predict outcomes in federal court.
- Cox’s art: Cox talks about making large acrylic pop-art paintings, usually while listening to true-crime material. He hopes to build a collection and possibly hold a gallery show or meet-and-greet.
The hosts close by encouraging viewers to follow the show for new episodes Wednesdays at noon.
📬 Never miss a Tom Simon & Matthew Cox Show video — every new upload summarized in your inbox.
Follow free
