The Hunter

Tom Simon and the Long Pursuit of America's Most Wanted

The mythology of the FBI often centers on dramatic arrests—the handcuffs clicking shut, the fugitive cornered, the years-long manhunt finally over. But for retired FBI Special Agent Tom Simon, the job was rarely about the moment of capture. It was about patience.

For much of his career, Simon worked in the world of violent criminals, organized crime figures, and fugitives who had spent years mastering the art of disappearing. The challenge wasn't simply finding them. It was understanding them.

"Everybody makes mistakes," Simon often tells audiences today. "The trick is figuring out which mistake they're going to make."

Simon entered the FBI during an era when the Bureau was increasingly focused on complex criminal enterprises. While many agents spent their careers behind desks reviewing financial records or preparing search warrants, Simon gravitated toward investigations that required knocking on doors, cultivating informants, and tracking individuals who had every reason not to be found.

Among the most memorable cases were those involving long-term fugitives—men who had successfully evaded capture for years, sometimes decades. Many changed identities. Some fled across state lines. Others hid in plain sight, working ordinary jobs and living seemingly ordinary lives while warrants accumulated in court files hundreds of miles away.

Simon learned early that fugitives rarely disappear completely.

They call relatives.

They visit old friends.

They develop routines.

Even the most disciplined fugitive eventually reaches for something familiar.

That understanding helped guide numerous investigations throughout his career. Working alongside local law-enforcement agencies, U.S. Marshals, and fellow FBI agents, Simon became known for his persistence. Rather than relying solely on databases and surveillance technology, he often focused on human behavior.

A fugitive could change his name.

He couldn't easily change who he was.

One case involved a violent offender who had spent years moving from state to state while avoiding authorities. Another centered on an organized-crime associate who believed he had successfully insulated himself through layers of intermediaries and false identities. In both instances, investigators eventually located their targets not because of sophisticated technology but because they understood the personal habits that criminals struggle to abandon.

Those years chasing fugitives also exposed Simon to a recurring truth about criminal investigations. Most fugitives aren't caught because they're outsmarted. They're caught because they're tired.

Living on the run creates its own prison.

Relationships become difficult.

Employment becomes unstable.

Trust becomes dangerous.

Eventually, many fugitives begin taking risks they once avoided.

That's when investigators move.

By the time Simon retired from the Bureau, he had participated in investigations involving organized crime figures, violent offenders, fraudsters, and fugitives whose cases stretched across multiple jurisdictions. The work was often frustrating and rarely glamorous. Most breakthroughs came after months or years of dead ends.

Today, Simon shares those experiences with audiences through podcasts, interviews, and public appearances. His stories offer a rare glimpse into a side of law enforcement that rarely makes headlines—the painstaking work of finding people who desperately do not want to be found.

In the end, Tom Simon's career was never really about arrests.

It was about understanding human nature.

And human nature, he learned, almost always leaves a trail.