From FBI Agent to True Crime Expert: The Career of Tom Simon

After more than two decades investigating fraud, terrorism and other federal crimes, retired FBI Special Agent Tom Simon has found a second career bringing an insider's perspective to private investigations and the growing world of true crime.

Simon spent approximately 26 years with the Federal Bureau of Investigation, serving from 1995 until his retirement in 2021. During his career, he worked in FBI field offices including Chicago, Honolulu and Jacksonville, handling cases that ranged from complicated financial crimes to national security investigations.

His background made him particularly well suited for following money.

Simon is a Certified Public Accountant, giving him specialized expertise when investigating Ponzi schemes, embezzlement, investment fraud and other financial crimes in which understanding accounting records can be as important as interviewing witnesses.

His FBI career, however, extended well beyond white-collar crime.

While assigned to Jacksonville, Simon worked with the Joint Terrorism Task Force and served on a human intelligence, or HUMINT, squad. That work included developing and handling confidential human sources, an area of federal law enforcement that relies heavily on an agent's ability to evaluate credibility, establish relationships and persuade people to cooperate.

Simon also received specialized FBI training in areas including interviewing, interrogation, undercover operations and asset forfeiture.

Some of his cases were serious; others were decidedly unusual. Simon has publicly discussed investigating a bizarre scheme involving a supposed Stevie Wonder benefit concert in Hawaii. The University of Hawaii had reportedly paid a $200,000 deposit for the appearance, only to discover that Wonder and his legitimate representatives were not involved.

After retiring from the FBI, Simon transitioned into private investigations and consulting. He operates Simon Worldwide Investigations, a Florida-based investigative firm handling matters including fraud, embezzlement, corporate investigations and other sensitive cases.

In recent years, Simon has also emerged as a familiar voice in the true-crime and podcast world.

He has appeared frequently on Matthew Cox's Inside True Crime, where he provides a former federal agent's perspective on criminal investigations, interrogation techniques, fraud schemes and high-profile cases. His appearances often give audiences a look at how investigators evaluate evidence and build federal cases — something television crime dramas frequently oversimplify.

Simon represents a growing group of retired federal investigators who have moved into media and private consulting after leaving government service.

For audiences fascinated by how criminals think and how investigators catch them, Simon offers something difficult to replicate: nearly three decades of experience from the other side of the interrogation table.