Reche Caldwell did not exactly have a successful NFL career. The former Florida Gators star is best known for being the guy who may have cost Tom Brady another Super Bowl ring by dropping a couple of key passes in the 2006 AFC Championship Game. What you may not know about Caldwell is that he was sentenced to prison time after his playing days ended.
After his disappointing playing career concluded, Caldwell returned to his hometown of Tampa Bay. In a lengthy feature from ESPN.com’s David Fleming that is worth reading in its entirety, Caldwell’s attorney said the former receiver was “jobless, he was bored, he had a bunch of money, and he didn’t know what to do with himself.” So Caldwell did what (hardly) any ex-NFL player would do — he got mixed up with the wrong crowd and started an illegal gambling ring. More from Fleming:
Before long, Caldwell was doing almost $225,000 in wagers each month. He didn’t like banks, so cash would be crammed into Maxwell House coffee tins and piled up everywhere, in the microwave and in crooked, Dr. Seuss — like stacks that stretched to the ceiling. What had been a sleepy little mom-and-pop car-detailing shop was overrun by as many as 40 cars and nonstop foot traffic from Friday through Monday — changes that were hard to conceal, seeing as how there was an elementary school across the street. “I see now, yup, not the greatest location for that kind of thing,” Caldwell says with a chuckle. “Too big, too fast. I laugh at my stuff too. What else can you do? I have to laugh. I really thought I was some kind of a criminal? All I know is, everyone kept telling me, ‘The police don’t care about this stuff, you’ll never get caught,’ and the next thing I know I’m headed to prison, saying goodbye to my kids, wondering: ‘What happened to me?'”
In early 2014, the feds raided the house where the gambling operation was set up. Caldwell was eating a sandwich at the time, and he didn’t even think much of the first flash-bang grenade shaking the building. He was eventually arrested, half-eaten sandwich and all, and charged with bookmaking and running a gambling house.
Caldwell didn’t learn his lesson. He was later busted for trying to purchase a large amount of MDMA — also known as Molly — on the internet. Did he have a guy? No, he just Googled it, and he ended up at the center of a sting operation. Because of that, he’s currently serving a 27-month prison sentence.
Seriously, go read the feature. It’s surreal.