Tommy DeSimone [organized crime]

Calvin

“Welcome to the infamous edition of the Headstones and Microphones where we use AI to step into the past through a researched, first-person simulation done through creative story telling of history's most infamous people. Now, let’s meet our guest.”

Calvin

"Welcome to the podcast. Let’s start at the absolute beginning, where the public narrative hasn’t yet distorted who you were. When and where were you born, and what was your given name?"

White Male Guest

"Hi Calvin. If we are looking at the absolute record, I was born on June 6, 1946, right in New York City, over in the South Ozone Park area of Queens. My given name on my birth certificate was Thomas James DeSimone."

Calvin

"What was your hometown and home life like as a child?"

White Male Guest

"Growing up in Queens back then, it was a busy house. I was actually the youngest of eight children born to my parents, Robert and Camilla. Money wasn't always easy to come by, and the neighborhood had a lot of different influences moving through it. Crime ran a bit in the family circles, too. Two of my older brothers ended up as associates with the Gambino family, and one of my sisters actually got involved with Jimmy Burke when she was pretty young. So, from the time I was a kid, that world was never too far from our front door."

Calvin

"Was there a story behind your name, or a nickname that stuck with you?"

White Male Guest

"Most people know the Hollywood version of me as Tommy DeVito, but on the streets, they called me 'Tommy D' or 'Two-Gun Tommy' because I had a habit of carrying a piece everywhere I went. Later on, because of the temper and the way I handled things, some guys started calling me 'Animal.' There was also 'Spitshine Tommy,' which tied back to a bad interaction I had with a guy named Billy Batts."

Calvin

"What were you like as a child, and how many years of schooling did you actually attend?"

White Male Guest

"I was a pretty skinny kid growing up, always trying to keep up with my older brothers and prove I was tough. School wasn't really my focus. By the time I was around fifteen years old, I was already out on the block selling hijacked cigarettes and making a couple hundred bucks a day, which was huge money back then. I walked away from the classroom early because the streets were teaching me everything I actually wanted to know."

Calvin

"What’s a decision that changed everything for you, but felt small at the time?"

White Male Guest

"It was 1965. I was nineteen years old and I got introduced to Paul Vario, who was a caporegime in the Lucchese crime family. At the time, it just felt like a young guy getting a chance to run with the big fish and make some real money. But looking back, walking into that crew and putting on that wiseguy suit completely locked in the direction my life was going to go."

Calvin

"Let's talk about your early run-ins with the law. Before the world knew your name for your most infamous actions, what was your very first arrest or interaction with law enforcement, and what were the consequences?"

White Male Guest

"One of my earliest official problems on paper happened in late 1969. I got pinched in November with a handful of other guys for criminal possession of stolen property after the law uncovered more than a million dollars in stolen goods sitting in a warehouse in Queens. Luckily for me, those charges ended up getting dismissed. Then, just a month later in December, I hijacked a truck full of liquor in Manhattan containing a few thousand dollars worth of alcohol. Got caught in Queens with two other guys, but that one just turned into a fine, and the charges eventually went away."

Calvin

"At what moment did you realize your name would never be forgotten?"

White Male Guest

"It had to be after the Air France robbery in April of 1967. Henry Hill and I walked right into the cargo terminal at JFK Airport using a duplicate key while the guard was on his dinner break. We walked out of there unchallenged with an empty suitcase packed with $420,000 in cash. When the airline discovered it on Monday, it turned into a massive national story. That was the moment we realized we could pull off the impossible, and the media frenzy proved the world was watching."

Calvin

"Did fame make you more dangerous, or did it simply expose who you already were?"

White Male Guest

"The notoriety definitely didn't slow me down; it just gave me the green light to be exactly who I was. I already had a reputation for being hot-headed and unpredictable. Once we were moving heavy weight and the money started piling up, I started carrying two guns and didn't think twice about using them. If anyone stepped out of line or insulted me, like a kid named Spider who didn't want to dance, I used them for target practice. The lifestyle just stripped away any hesitation I might have had."

Calvin

"Who do you believe betrayed you first: a person, society, or your own instincts?"

White Male Guest

"In our world, it’s always the people closest to you. You spend your life looking over your shoulder at the cops, but it’s the guys you eat dinner with who end up setting the trap. My own instincts were to always strike first and show no weakness, but when you break the rules of the commission—like taking out a made man without permission—the loyalty inside your own crew completely evaporates."

Calvin

"What’s a unique habit or a random fact about you that would surprise people?"

White Male Guest

"When I was out doing truck hijackings, I would always carry my gun inside a plain brown paper bag. Henry Hill used to joke that when I was walking down the street, it looked like I was bringing you a sandwich instead of a loaded .38 caliber pistol."

Calvin

"Did you have any known rivalries that defined your career?"

White Male Guest

"My biggest and most fatal rivalry was with William 'Billy Batts' Bentvena. He was a made man with the Gambino family. He had just gotten out of prison in 1970 and ran into me at a nightclub. He decided to mock me in front of everyone about my old days shining shoes when I was a kid. In our world, you don't let an insult like that slide, regardless of a guy's rank. That rivalry ended very badly for him in the back of a car."

Calvin

"When the law finally closed in, how exactly were you brought to justice? Walk me through the final arrest, the charges that ultimately stuck, and the legal outcome of your trials."

White Male Guest

"The funny thing is, the traditional law never did close in on me. I never stood before a judge for my final actions, and I never saw the inside of a prison cell for the Lufthansa heist. On January 14, 1979, I just vanished off the face of the earth. I walked out of the house and never came back. Justice in my story didn't come from a courtroom or a verdict; it came quietly from the streets."

Calvin

"What’s the craziest rumor ever told about you, and what part of your story has been exaggerated the most?"

White Male Guest

"The movies love to give everything a clean, dramatic ending. In the film adaptation of our lives, they show me walking into a room, getting shot in the face, and being buried in a closed coffin. But the reality is much more mysterious. There was no funeral, no closed coffin, and my body was never actually found. Hollywood sold certainty where reality only left a black hole."

Calvin

"What is the biggest misconception people have about your life?"

White Male Guest

"People look at the movie and think I was just a completely unhinged cartoon character who woke up looking for chaos every single second. While I absolutely had a vicious streak and did terrible things, a lot of what we did was highly organized, methodical business—like planning logistics for airport cargo thefts and running multi-million dollar operations. We weren't just street brawlers; we were running a highly sophisticated criminal enterprise."

Calvin

"When, where, and how did you pass away?"

White Male Guest

"Officially, I disappeared on January 14, 1979, in New York City at the age of thirty-two. Because my body was never recovered, the exact date, the precise location, and the definitive cause of my death remain unverified by the authorities to this day. I simply walked into the shadows and became a ghost."

Calvin

"Do you have any closing remarks about the interview or the stories you shared that you would like to share with the listeners before signing off?"

White Male Guest

"I’d just tell people that the glamour you see on the movie screens isn't the whole picture. It looks fast and exciting, but it ends with you looking over your shoulder every minute of the day until you disappear completely. Thanks for letting me clear up the record, Calvin."

Calvin

"And that wraps up another conversation from beyond the grave. Thanks for joining us on The Headstones and Microphones Podcast. Remember—Do better with the life you have been given and choose to do good in this life. Please help spread the word by sharing and following the pod."