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From FBI Agent and Fraudster to Podcast Partners: Tom Simon and Matthew Cox Launch New True-Crime Show

Writer: Helen Diaz
Helen Diaz
Sep 18
3 min read

TAMPA, Fla. — On paper, retired FBI agent Tom Simon and former fraudster Matthew Cox probably shouldn't be friends.



Simon spent 26 years with the FBI investigating criminals. Cox spent years committing sophisticated bank and mortgage fraud before becoming a federal fugitive and eventually serving 13 years in prison.


Both men even appeared on CNBC's American Greed — Simon discussing criminals he investigated and Cox for the considerably less flattering reason of being one of the criminals featured by the show.


Now, the unlikely pair have joined forces.


The Tom Simon and Matthew Cox Show launched this month on YouTube and Spotify, turning a popular recurring segment from Cox's established Inside True Crime podcast into a channel of its own. The early response has been explosive, with the new program generating hundreds of thousands of views across its content during its first week and immediately establishing itself as another potentially significant player in the rapidly growing true-crime podcast market.


Simon has publicly promoted the new program as an extension of the unlikely friendship the two developed through their previous appearances together.



Guess the Sentence


The centerpiece of the show is remarkably simple: Simon tells the crime story. Cox guesses the sentence.


The segment, called "Guess the Sentence," originally developed during Simon's appearances on Inside True Crime. Its success eventually convinced the pair that the concept could support a show of its own.


Simon arrives with a collection of real criminal cases, many involving federal investigations. Some involve fraud, corruption or financial crimes; others venture into far stranger territory.


He walks Cox through the case almost like a prosecutor presenting evidence: who the defendant was, what he or she did, how the crime worked, the amount of money involved, the victims and ultimately the criminal charges.


Then he stops before revealing what happened at sentencing.


That's when Cox has to make his guess.


The rules have varied somewhat between appearances, but the challenge remains the same: use the facts of the case to determine how much prison time the defendant received.


Previous versions have awarded Cox a point when his prediction falls within an agreed range of the actual sentence.


What sounds like a simple guessing game works because Cox has an unusual advantage.


He spent more than a decade inside the federal prison system.


Cox understands sentencing guidelines, criminal histories, loss calculations, cooperation agreements and the sometimes surprising differences between the crime someone commits and the sentence ultimately imposed.


That means viewers can play along while watching someone with firsthand experience attempt the same calculation.


An Unlikely Chemistry


The show's other advantage is something considerably harder to manufacture: chemistry.

Simon represents law enforcement. Cox represents the criminal world.


Yet their conversations rarely feel adversarial.


Simon brings decades of investigative experience and an encyclopedic collection of unusual cases. Cox approaches those cases from the perspective of someone who understands how criminals rationalize decisions, make mistakes and eventually get caught.

The contrast creates both insight and comedy.


The two have already developed a substantial history together. Simon has appeared in more than 20 installments of the sentencing game on Cox's original program, according to one of their recent episodes.


A recent Inside True Crime episode involving several federal fraud cases was effectively used to hand viewers over to the new channel, with the second portion continuing on The Tom Simon and Matthew Cox Show.


It's a clever launch strategy: take an established segment with an existing audience and give it a dedicated home.


More Than a Game Show


The format also solves a problem that confronts many true-crime podcasts.


There are only so many ways to retell a murder.


Simon and Cox instead have access to an almost unlimited supply of criminal cases. Fraudsters, corrupt executives, embezzlers, drug traffickers, cybercriminals and thieves can all become contestants in absentia.


Each case provides a mystery, but the mystery isn't necessarily who did it.


The viewer already knows the defendant committed the crime.


The question is:


What punishment did they get?


That distinction gives the program an interactive quality. Viewers can make their own prediction before Cox announces his and then discover whether they understand the criminal justice system as well as someone who actually spent 13 years inside it.


The show also gives Simon and Cox room to expand beyond the game. Simon's launch announcement says the program will include conversations about their dramatically different lives and histories in addition to Guess the Sentence.


And that may ultimately be where the show's greatest potential lies.


True crime is crowded with former detectives, journalists, attorneys and criminals telling stories. There aren't many shows pairing the former FBI agent with the former federal fugitive. Simon once made a career catching criminals. Cox once made a career trying not to get caught.


Now they're sitting across from each other trying to answer a completely different question:


How much time did the guy get?

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