It’s every sports fan’s biggest dream and worst nightmare. The chances of sinking a basketball through the hoop from the other side of the court are astronomical. But the only thing worse than missing the shot is making it only to be denied the prize money on a technicality. That was almost the story of Dan Calhoun, had it not been for one person: Michael Jordan.
The million-dollar shot took place on April 14th, 1993, at a basketball game where the Chicago Bulls were facing off against the Miami Heat. During a timeout in the third quarter, the stadium ran a promotion that offered a million dollars to whichever fan could sink the basketball through the hoop. The catch: they would have to throw it from the free-throw line on the other end of the court, a 75-foot shot that had less than a 1% chance of going in.
19 people had attempted the shot that year. Barely three had made it anywhere close to the backboard, let alone made it in. Only one person had ever made the shot before–a fan from 1989, who had won a car for his efforts.
This time, the stakes were higher. A million dollars were on the line. When Dan Calhoun was selected from the crowd to participate, he knew the challenge ahead of him. He couldn’t throw it two-handed. He would have to throw it like a football, praying that his gamble would succeed. But despite the impossibility of the shot, he knew he would succeed.
“I knew it was in the moment it left my hand,” Calhoun said after making the shot that, despite all odds, sank right through the net.

It was the shot that changed everything. The stadium erupted into cheers, as Calhoun was swarmed by the Chicago Bulls and congratulated by Michael Jordan himself. The referee gave him the basketball that made the prize-winning shot, and everything seemed like it was turning up roses.
Until the insurance company stepped in.
The contest was sponsored by the Chicago Bulls, Coca-Cola, and Lettuce Entertain You restaurant. But to cover the payment, they had to work with an insurance company called American Hole ‘N One Inc. The company looked into Calhoun’s past and discovered that he had played basketball in high school and college, albeit never professionally. Citing the fine print of the contract, they voided the payment on a technicality.
Calhoun was an office supplies salesman making $5 an hour. To him, a million dollars could be life-changing. Thankfully, the sponsors of the event were outraged at him being denied the money and promised to cover the prize if the insurance company did not. But it wasn’t until after the fact that Calhoun found he’d had a man on the inside advocating for him. After successfully getting the first of twenty $50,000 payments, Calhoun tracked down Michael Jordan to ask him to autograph his basketball.
“Did you get your money?” asked Jordan.
When Calhoun replied that he had, Jordan told him, “We made them give it to you. We were upset that they were trying to not pay you.”

Although Calhoun didn’t get his million dollars right away, he received $50,000 a year for the next twenty years. Sadly, after taxes, this meant that he earned only $38,000 a year. But while the money wasn’t enough to make him rich, it was enough to help pay for one of his kids to go to college and obtain a medical degree.
This story could have had a tragic ending were it not for the efforts of Jordan and the sponsors who forced the insurance company to pay up. The Calhoun Shot, also known as the Immaculate Connection, not only changed Calhoun’s life–it changed the history of sports contests forever.