It’s late in the fourth quarter. Your team is losing, but that doesn’t matter anymore. You’ve got a prop bet on the quarterback’s completions, a live bet on the next field goal, and another game starting in twenty minutes. When it’s over, a friend asks, “Did they win?” And you don’t really know how to answer.
Bob Gray knows that feeling. He lived it for years. This week’s Sunday Project was all about Bob: where gambling took him, and how he now spends his life helping people find their way out.
"A very successful failure"
Bob doesn’t sugarcoat his gambling. “I was a very successful failure,” he said. “I got really clever and creative. I knew how to get money, and I knew how to manipulate my creditors, my friends and my bookies.”
Like a lot of people who gamble, he believed he had an edge. “I used to think if I had a bet on a game, I had influence on the outcome,” he said. “I used to think, well, those odds don’t apply to me. Because I’m smart, and I know what I’m doing.”
They did apply. And the gambling swallowed his time as well as his money. “I worked 40 hours a week, but I gambled 60 hours a week,” he said. Looking at lines. Looking for money. Looking for the next way out.
He’d take a friend to Saks Fifth Avenue, charge a $2,500 suit to his credit card, and ask the friend for $500 in cash. “I’d lose it at the racetrack that afternoon, and then that debt would be on my credit card for the next seven years at 19% interest. Crazy stuff like that.”
Today, Bob carries a collection of his old credit cards, all cut up, to events and conferences. It’s a reminder of how deep it went.
The day $40,000 wasn't enough
For Bob, the moment it turned truly ugly was a day he won.
He was driving home from the Del Mar racetrack with a shoebox holding $40,000 in cash. Most people would call that a life-changing win. For Bob, it was nothing.
“It was not enough, because I owed this guy, that guy, my rent, my car,” he said. “I was a million dollars in debt, and that $40,000 meant nothing. It just meant, well, now I could bet 40,000 more, maybe try to get out.”
Becoming someone he didn't recognize
What hurt most wasn’t the money. It was who he’d become.
“I had betrayed a lot of friends. Family members,” Bob said. “You become a liar and you become a thief.”
And like so many people in the grip of a gambling problem, he felt completely alone with it. “I thought that I was uniquely different. Nobody had my problem.”
Recovery isn't a straight line
Bob joined Gamblers Anonymous in 1993. He’s honest that his recovery hasn’t been perfect. He’s had three restarts: once after 18 months, and again after 12 years.
One of those slips was a serious one. He lied to his wife, got caught gambling, and it was devastating. One of his sponsors told him something that changed how he approached recovery:
“Right now, Robert, it’s not important if your wife trusts you. It’s important if you trust you.”
So he started small. Keeping his word to himself. Saying he wouldn’t do something, and then not doing it. “It’s all about evidence,” he said. “Things will be self-revealed. It takes time.”
Bob is still married. His wife was in the next room during the webinar, and his kids are flourishing. “There’s no more secrets,” he said. “Secrets are where bad ideas go to hide.”
He doesn’t pretend it’s easy now. “It’s a constant struggle for me. That’s just part of life.”
Even small things took time to relearn. Early in recovery, he was scared to buy a couch. “I didn’t think I deserved a couch,” he said. “But then I learned that I deserve everything.”
How Bob helps people now
Bob isn’t a therapist. He calls what he brings “shared experience and lived experience.” And he uses it every day.
“I don’t know you, but I know you”
When Bob meets someone in crisis, this is the first thing he says. “The common denominator for people that get into trouble is we have lost the ability to control it.”
“You’re not a gambler,” he tells newcomers. “You’re just somebody who gambled. And now you don’t.”
"Call me, I'll take your bet"
Bob doesn’t officially sponsor people, but he tells them he’s available 24/7. And he means it.
He has an unusual offer for young guys who feel the urge to bet. “If you want to make a bet, and you need that to get your jollies, call me. I’ll take your bet. You’re not gonna get paid if you win, and more importantly, you don’t have to pay if you lose. Give me a thousand on Cincinnati. God bless you, man.”
It sounds like a joke, but it gives someone a way to ride out the urge without losing their rent.
Painting the picture
Bob’s real gift is imagery. He helps people step back and actually see what they’re doing.
“You’re putting hard dollars on men in tights running up and down a field, chasing a ball,” he said. “For you, those are hard dollars. Your rent, your car payment, your tuition. For these guys on the field, it’s just Tuesday night. They’re getting paid if they win or they lose.”
He jokes that he’s become an expert in prediction markets. “I can predict what would happen to me if I were to gamble. I’d lose my house. I’d lose my family. I’d lose my friends. I’d lose my self-respect. I would lose everything.”
And he asks a question that stops people in their tracks: What are you swinging for? “You trying to buy a house in Malibu? Go around the world in 80 days? When do you realize that you hit it or you didn’t hit it? It’s endless.”
The not-to-do list
Everyone coming into recovery faces a huge to-do list. Bob keeps it simpler. He gives newcomers a not-to-do list, with just four things on it:
- Don’t lie.
- Don’t cheat.
- Don’t steal.
- Don’t gamble.
“There’s a billion things you’re gonna need to do in the coming weeks, months or years,” he said. “But there’s only four things you can’t do.”
Filling the time
Bob knows that quitting leaves a gap. “Okay, I’m gonna quit. But now what? What are you gonna do with your time, during the games, on Saturdays and Sundays?”
For him, it was music. And eventually, sports came back too, but differently. “I’m able to watch sports, because it’s a beautiful thing. I don’t care what happens. I could walk away on a double overtime with 30 seconds to go. Who cares? It has no impact on my life.”
"They've infected the game"
Bob spent his career in marketing, and he now uses those skills to push back against the betting industry. He believes sports betting has changed the games themselves.
“In the old days, you made one bet, and you were stuck with that bet,” he said. “Now you have another 2,000 bets.” It’s no longer about the team. It’s about the bet.
His slogans have become part of the Stop Betting Sports message:
- They’ve infected the game.
- When the bet becomes the story, the game is the stage.
- Are you a fan, or are you a customer?
- Free throws aren’t free anymore.
- You win every bet you don’t make.
He puts up posters around town, designed a Stop Betting Sports jacket with a QR code that gets people asking questions wherever it goes, and has stress balls ready to throw into crowds at games and pep rallies. Living near the Lakers, the Chargers, the LA Kings and a WNBA franchise, he’s planning to take his story straight to their headquarters.
A caddy in life
Dan Field, LCSW, Clinical Director of Westside Gambling Treatment, often calls Bob when a client is heading to their first Gamblers Anonymous meeting, so they’ll see a friendly face when they walk in. “It really exemplifies that idea of you’re not alone,” Dan said. “There’s nothing phony about it in any way.”
But the compliment Bob treasures most came from a young man he’d spent about a year supporting. “He sent me a text, and he said, you’re my caddy in life. Carrying my clubs. That really felt good.”
Bob believes people need both kinds of help: professional treatment, and people who’ve been there. “If your therapist never needed a field goal with 30 seconds to go in double overtime, you have to live that to feel it,” he said. “Hanging out with people that speak the same language, that’s been the key to my success.”
On this side of the fence
For Bob, Gamblers Anonymous is, first and foremost, a fellowship. “The cornerstone of my recovery are the friends that I’ve met,” he said. “A group of people heading in the same direction.”
Since 1993, he’s watched thousands of people come through the doors. The ones who stay have shown him what’s possible. “I’ve seen divorces fixed. Law licenses reinstated. I’ve seen people go to jail and come back and now own a home and a business.”
His message to anyone still gambling is simple:
“Gambling will always be the same. Win, lose, nothing is ever going to change on that side of the fence. On this side of the fence, everything is possible. Everything.”
If you’re not sure where to start, Bob shares one of GA’s favorite lines: “Stick around for 90 days. And if you don’t get better, we’ll be glad to reinstate your misery.”
Where to get support
- Gamblers Anonymous holds meetings across the US, in person and online. Dan suggests trying at least three meetings, in person if you can, because every meeting feels different.
- Stop Betting Sports is launching an open group for people who are struggling to stop gambling, led with the help of peers who’ve been there.
- Reach out to us at stopbettingsports.com. If you’re in another state, the UK or Australia and don’t know where to turn, we can connect you with help.
You can watch every Sunday Project on YouTube at Stop Betting Sports. Find out more at stopbettingsports.com.
If you or someone you love is in crisis or thinking about suicide, call or text 988 (Suicide & Crisis Lifeline) in the US.
Support is available
Stop Betting Sports hosts free weekly support spaces for people affected by gambling – including parents and loved ones.