Darrin Landes: Sports Packages for the Rich, Then Addiction and Prison
“I can walk away from the truth, but he doesn’t walk away from me. I’m the one that lets go. I’m the one that chooses to do my own thing.”
Darrin Landes is the kind of guy who could get you Masters tickets. Kentucky Derby tickets. Super Bowl tickets. He built an empire selling sports packages to Fortune 1000 companies. But underneath the success was a gambling addiction that had him owing mob-connected bookies in Chicago hundreds of thousands of dollars—and doing whatever it took to pay them off.
What got me about Darrin’s story is that he went to prison twice. The first time taught him he needed to get sober. The second time taught him he couldn’t live in the gray.
Growing Up in His Father’s Shadow
Darrin grew up in a very athletic family near St. Louis. His father played professional baseball for the Yankees. Most of his summers and winters were spent at fields and courts. His sisters played sports. He played sports. That was their life.
“I was very proud of it,” Darrin told me about his father’s career. “But it also caused a lot of insecurity. I felt like I had to measure up. He was tough on me. He always coached me. I was probably worked harder because he would put more pressure on me.”
Darrin didn’t have the god-given talents his father did. And he admits he didn’t work at it the same way either. He went to private high school, was an average student, started at a community college, then went to Southwest Missouri State without finishing. But he wasn’t directionless—his first job was at Adidas as a sales rep.
From Adidas to the Sports Package Business
Adidas moved Darrin to Dallas to take over their second-biggest market. The partying started there. A lot of dinners. A lot of drinking. Chasing the almighty dollar.
“I was so bored on the road,” Darrin said. “I would call a hotel and say, ‘Where’s the closest bar?’ That’s where my addiction to alcohol began.”
He got married. His wife hated St. Louis and demanded they move after exactly one year. They landed in Sarasota, Florida, where Darrin joined TPC Prestancia, a country club. That’s where he met someone who changed everything.
They started an amateur golf tour. After 9/11, they landed Anheuser-Busch as a sponsor—over $3 million a year for the Michelob Bolter Tour. They expanded to 55 markets with 7,000 members.
The sports packages came next. Masters tickets. Kentucky Derby. Super Bowl. Final Four. They sold them to the Fortune 1000 companies whose executives wanted to take clients or reward staff. The money was flowing.
The Gambling That Took It All
While still in Dallas, Darrin got introduced to sports gambling. For an addict, the dopamine hit of winning—even five bucks on a football game—was irresistible.
“I was putting $5,000 on the coin flip of a football game,” Darrin admitted. “Stuff I look at now and think, you are crazy for doing that.”
He got behind. Way behind. His bookies were connected to the mob out of Chicago. When he owed them $8,000 one week, he’d hop on Craigslist and sell Masters packages to cover it. Rob Peter to pay Paul.
“It was fine at first,” he said. “But then trying to keep up with that… you can’t.”
His drinking got worse. His marriage fell apart—they were both alcoholics, more drinking buddies than spouses. He was sitting at a bar that would open early just for him, watching horse racing and Keno, drinking all day while bookies messaged him asking where their money was.
Eventually, he had 30 to 40 people he was playing this game with, selling tickets to events that were months away, hoping to figure it out before the date came.
The Bottom of the Lake
The pressure became unbearable. Darrin was at the bar, drinking, on his way to the casino, when he woke up being talked to by a park ranger in a canoe at Creef Cor Lake.
“I just wanted to die,” he said. “The pressure was so intense. I felt such shame and guilt. My family was standoffish. My friends were… I felt alone on an island.”
He prayed: God, help me. Two days later, he was on his way to rehab in Newport Beach, California. That’s where the transformation began. But he also knew there were consequences coming.
The FBI visited him at rehab. They had a binder full of contracts from packages he’d sold to companies. Darrin stopped them immediately: “Everything in there is true. All I ask is that you let me finish rehab.”
They did. He cooperated fully. He was sentenced to a year and a day at Montgomery, Alabama—about eight months with good time.
The Gray That Brought Him Back
Darrin got out sober and feeling good. But he was starting over at 42 with nothing. When a buddy from Anheuser-Busch called needing Final Four packages, Darrin knew he couldn’t do it—part of his probation was staying out of the ticket business.
“Keep it on the down low,” his friend said. “No one will ever know.”
One deal turned into more deals. Soon Darrin was back in the game, telling himself it was legitimate tickets this time, nothing fraudulent. But the voice in his head kept saying: What you’re doing is not right.
His AA sponsor told him what he needed to do. Darrin called his probation officer and confessed.
“She said, ‘I knew that,’” Darrin recalled. She told him not to do it again. Months went by. He thought he was in the clear.
Then she called. He’d picked up a new charge. He was resentenced to two and a half years in Pensacola.
Learning to Live in Black and White
Darrin went back to prison feeling like the biggest failure. Two-thirds of inmates return within three years. Three-quarters within five. He’d become exactly what he’d sworn he wouldn’t be.
But something changed in Pensacola. He landed a sweet job working on the golf course at the naval base—mowing greens on Pensacola Bay, right next to the ocean. He was still incarcerated, but his mind was different.
“That was the moment I said I cannot live in a gray world,” Darrin told me. “Everything’s got to be black and white with me. I can’t afford the gray.”
He dug deeper into recovery, into faith, into the work he’d been half-assing the first time around. When he got out, he knew he was never going back.
The Comeback
Today Darrin runs a successful business as a third-party seller on Amazon. He buys closeouts from Sam’s, Costco, and Target at pennies on the dollar and resells them on Amazon. Two years in, and he wouldn’t change it for the world.
His relationship with his father is the best it’s ever been. They’ve made amends. He keeps his circle small. He’s plugged into AA and surrounded by people who will call him out the second he starts to deviate.
“Our mistakes don’t define who we are,” Darrin said. “There are a lot of really good people that have done really stupid stuff.”
His biggest takeaway? “I can walk away from the truth, but God doesn’t walk away from me. I’m the one that lets go. When I really surrendered everything is when it all turned.”