I've Lost $500,000 Betting on Sports and Don't Plan to Quit

How gambling on games took over one man's life
Published: 29 May 2023

In 2018, the Supreme Court struck down a 1992 federal law banning the expansion of sports betting, allowing states to implement sports gambling. Several legislatures quickly did exactly that and for the first time in our nation’s history, Americans no longer needed to travel to Las Vegas to lay a wager on a game. They could do it from the comfort of their homes, with the mere tap of a finger, thanks to the proliferation of sports betting apps.

The sports betting industry has exploded since then, with revenues expected to reach $39 billion annually in 10 years. With that explosion in gambling activity comes an increased risk of gambling addiction. At particular risk are young men, ages 18 to 24, who account for the majority of new problem gambling cases. (The legal age for sports gambling is 18 or 21 years old depending on the state.)

For the second installment in our new series on The Secret Lives of Men, Esquire spoke to “Johnny Overs,” who started betting on sports in his late teens. He earned his nickname by always taking the over on NBA games, and the habit quickly grew into a full-blown addiction. He estimates he’s lost more than $500,000 over his life on sports gambling. Although he recognizes he has a gambling problem, Johnny also says he has no plans to stop.

“Johnny Overs,” 39, The Bronx

Iwas gambling when I was just a teenager. I was great at basketball growing up. I was dunking in eighth grade, and I wasn’t even six-foot then. I would go to the park and the tallest kid would be like, “I bet I can dunk on you.” I’m like, “I bet you can’t.” They would throw a dollar or two down and I would stand under the hoop and they could never throw it down on me.

My friends and I would be in the park playing fives all day, from 11 a.m. until the parks department locked the gates at night. Sometimes we’d go to different neighborhoods and play kids there for $20 a guy. We would play guys who played for St. John’s and Fordham, and we’d wash the floor with them. Our squad was like the white Harlem Globetrotters — we’d twirl a basketball on our fingertips and then place it on a little kid’s finger. Parents loved it.

Someone would challenge me to a shoot-off—free throws or 3-pointers, and people on the sidelines would bet $5, $10, sometimes $20 a shot. If I won them money, they’d share some of the winnings with me. That’s how I would get a little money here and there.

I got a scholarship to play at this fancy prep school in Westchester County. It was like a $5,000 a year school at the time. I was getting offer letters from Duke, North Carolina, West Virginia, Virginia. I could make a million excuses about why it didn’t work out, but truth is, I was just lazy. I didn’t want to wake up at 5 o’clock to catch a train to catch a bus to Westchester. It wasn’t for me. But I could have been that guy.

After that, I went to school in the Bronx, which gave me free reign to do whatever the fuck I wanted. I’d come and go as I pleased. I ended up getting transferred to another school in Washington Heights because I got in a fight. I was a lion back then. I grew up thinking, It’s better to live a day as a lion than a lifetime as a lamb. Never let anyone take advantage of you.

I wasn’t gonna go to school in Manhattan—the commute was longer than it took to get to Westchester—so I dropped out and started working construction.

My first job, this old Irishman, Kieran, straight from the island, said, “What are you doing here? You’re just a kid.” I said, “I’m here to make money.” He gave me the worst possible job: pulling the rope to lift grout up four stories of a building. My hands were bloody by the end of the day. I hated that fucking guy, but looking back, he was trying to teach me a lesson. Don’t end up like me, a beaten-down old drunk. Go back to school. I was like, “Just give me the money, man.”

I was making $27 an hour, union money, good scratch for a 17-year-old kid, and that’s when the sports gambling started.

My first bet, my friends and I put in $20 each and all three of our picks hit. We won $480, $160 a guy, eight times our money. The dopamine was overflowing, and that’s what you end up chasing.

For a while, I placed bets through a friend, but when I was 19, I got my own line of credit and was able to place bets myself. They used to call me “Johnny Overs” because I would take the over on every game. I just wanted to watch a fun game and see points scored.

The downside to being good at sports is that you think you know sports better than most people and that means you can gamble on it successfully. I was naive. I thought it was simple. Well, this team is better than that team, so obviously they’ll cover the spread. But you quickly realize that’s not true. The oddsmakers have the advantage. If there are 12 games in a day, they might be wrong on one or two.

My first week I lost $5,000. One dude gave me a $5,000 a week limit at $1,000 a game. I lost my first $1,000 bet and was like, It’s alright, I’ll pick it up. So then I’m chasing. Another $1,000, another $1,000.

I was devastated. I thought, I might have to go to jail, because this isn’t gonna end well. My betting isn’t done through an app with a casino or a gaming company. All my betting is done with local bookies, organized crime, but I don’t want to get into that. If you don’t pay it back, well …

"When I was really down, my mom would bail me out. She gave me 40 grand once."

I thought I was gonna have to hurt the person who came asking for the money or do something stupid to get the money. I had some friends who, if it really came to it, they could make my debt go away, but I didn’t want to involve them. It’s a dice roll with that, you don’t know who’s gonna come out on top.

My grandmother saw me upset and asked what was wrong. I told her, and she gave me the $5,000. That was a month’s salary for me at the time. I told myself, That’s it, I’m not doing gambling anymore. I’m gonna slowly pay this back over time and never gamble again. I never wanted to feel that low again.

A few days later, I thought, I’m gonna make back double grandma’s money in a week. Now I’m down $5,000 again and chasing another $5,000. So I started opening multiple accounts with different bookies. It’s a slippery slope. You can’t win. You don’t win.

I lied to myself for a long time, telling myself I didn’t have a problem. I hid it from my friends, especially the ones in the streets. I was losing a lot of money and if they knew about it, it would be an issue for other people. I didn’t want anybody going to jail over something I did. I was very secretive. I would be like, “Oh, someone’s calling me,” and go into the backyard and make five bets.

I would bet on football every once in a while, but I mostly bet on basketball. The NBA is big on Mondays, Wednesdays and Fridays. There can be 12, 14 games a night. Games at 7 o’clock, 8 o’clock, 9 o’clock and then the West Coast games. I would make a three-team parlay on the 7 o’clock games. I’d try to do the same with the 9 o’clock games, and maybe again at 11 o’clock or midnight. Or I would bet all the 7 o’clock games. You bet those, you’re already down $3,200 and chasing. There were five or six years where I routinely lost $3,000 a week. Fortunately, I have a good job. I work for a utility company. I make $200,000 a year.

If I bet a game, I watch it at home by myself. I don’t like to be around anyone. That’s one of my biggest gambling regrets: it made me hate sports. I used to love sports. Watched them 24/7. Now I can’t watch them without thinking of what they took from me. It just consumes your life. You could be on a date with the hottest chick in the world, and you’d be distracted, looking at the lines, seeing who’s injured and not playing tonight’s game.

It doesn’t help that my friends are huge gamblers, too. Their losses exceed mine even, and I’ve lost $700,000 over my life, easy. My friends and I were addicted to money. We all wanted to have jewelry, cars. I spent my money on clothes — sneakers, belts, jackets, a Rolex. I have 150 pairs of shoes. At least 75 are Yeezys.

My lowest point was when I was down $25,000. I didn’t have it and I was contemplating doing something really irrational. Thankfully, that didn’t happen. We had a sit down and I agreed to pay off the debt over six months, with zero interest.

You’d think one time like that would have solved my problem, but no, there were like 10 times like that. How much money can one person blow?

I won $100,000 on Super Bowl boxes one year. Five days later, I'm broke.

When I was really down, my mom would bail me out. She gave me 40 grand once. She had to choose between giving me her savings or me having to hurt somebody. I hate that I put her in that situation. She’s probably given me $200,000 total, and that’s her retirement. She was a bookkeeper (the legitimate kind) for a construction company. She doesn’t have a pension.

My mom is always going to think of me as that person. I’ll always be that fuck up to her. In hindsight, I think it would have been better if I had just left town and left everybody alone. They would be better without me. They wouldn’t have my burdens.

I won sometimes, too. I won $100,000 on Super Bowl boxes one year. I could have put that money in the safe, but no, I went to Atlantic City, got a big high-roller suite. Five days later, I’m broke. Sometimes I’d be up $15,000, $20,000 in a week. I’d get the envelope and go to a strip club and wake up with random women. The biggest high was when I was up big and I’d come home and start handing money out. Like it was Christmas. I wanted everyone to know how generous I was. “Here’s 20 grand for you, mom. Here’s $10,000 for you.”

My father wasn’t in my life growing up but I met him as an adult and I discovered he was a degenerate gambler, too. He was a manager of a Chase Bank and went to prison for embezzling money to fund his gambling habit. Did 24 months, I think. Now he goes across the country speaking about his addiction, running Gamblers Anonymous meetings. I wanted to say, “Look at these genes you gave me,” but I didn’t. I can’t blame him. You make your own decisions in life.

I still gamble. I made a bet yesterday. I just picked up $800 I won last week.

The other day, my cousin and I were watching the Dallas Cowboys and he was going nuts because he had $100 on the over and the Cowboys kicker kept missing extra points. I was like, $100? That’s it? That wouldn't even raise my heartbeat. My thought was, Okay, onto the next game. That’s the sad part.

Originally published on Esquire US

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