Young holds a unique position on this list because he went to jail twice on the same day. The first was for a DUI in San Clemente, California. It’s obviously wrong, but it happens and it’s not weird enough to make it onto this list in isolation. But the former Detroit Lions’ wide receiver did something incredibly foolish to get himself arrested for a second time.
After stopping him, the police obviously impounded his car. Young decided to steal his car back from the tow yard but didn’t have much luck. Young enjoyed the hospitality of Orange County police officers twice in the space of 15 hours. Then, three days later, they arrested him again for breaking into a house and stealing from a convenience store. Later, his father explained that Young experienced concussion symptoms after high school.
A two-time All-Star, Perez had a solid career in MLB. He spent the majority of his career with the Cleveland Indians but also pitched for the Cardinals and the LA Dodgers. Meanwhile, he was a fan of marijuana but the problem was that the law in Ohio didn’t approve of this. Perez had to find a way to get his weed to his house without giving away his identity. His solution was incredibly foolish.
Perez ordered his marijuana delivery using his dog’s name. However, this didn’t work very well and police pressed charges against both Perez and his wife. Furthermore, Perez had millions in his bank account. He could have easily afforded different arrangements that didn’t involve his house or his dog at all. But he didn’t and gave us this story instead.
There are a time and a place for a joke, but usually, that isn’t the courtroom. Unfortunately, somebody forgot to mention that to Johnson, because he really messed things up for himself by showing foolish disrespect in front of a judge. After his lawyer secured a plea deal for her client, Johnson undid all her good work. The judge told him that he should thank his lawyer for keeping him out of jail. So Johnson slapped her on the butt.
The Cincinnati Bengals star had violated the terms of his parole for another offense and faced 30 days in jail. But his lawyer successfully pled for leniency. However, Johnson’s blatant disrespect and sexism incensed the judge, who refused the deal and sentenced him to the full 30 days. In the end, Johnson only spent a week behind bars because he apologized to the judge. It was still extremely dumb.
O’Byrne spent a few years in and out of the NFL as he played for the likes of the Maple Leafs, the Colorado Avalanche, and the Montreal Canadiens. Furthermore, he spent a number of seasons on the European hockey circuit. Outside of the sport, O’Bryne enjoyed a good party. But one night in a club, the player got his wires crossed. Instead of asking a girl for her phone number, he stole her phone.
It’s an extremely interesting pick-up move because you can guarantee that the woman will come after you. But the problem is that she might bring the law with her. What was probably hilarious in his mind didn’t translate well as a dating technique. Instead of swiping her belongings, he should have swiped right on Tinder. As a professional athlete, he might have had some kind of chance with her.
After going on trial in one of the most infamous murder trials in U.S. history, the wisest thing to do would be to keep your head down. A court controversially acquitted Simpson and gave him a second chance. However, the former football star couldn’t stay out of trouble. In 2007, Simpson and a group of friends burst into Bruce Frumong’s Las Vegas hotel room and held him up at gunpoint.
Simpson alleged that Frumong had stolen some of his sports memorabilia. However, the victim, a dealer in such items, denied this, and a court sentenced Simpson to 33 years in prison for his actions. After serving for nine years, Simpson finally walked free in 2017. In sum, it was extremely foolish of him to give the court an opportunity to lock him away. They obliged happily.
Here’s a classic. Robinson wanted to relax the night before he played in the Super Bowl. The Atlanta Falcons was supposedly extremely religious, but this didn’t stop him from meeting up with a hooker. However, he didn’t realize that the first ‘prostitute’ he encountered was actually an undercover police officer. She slapped on the handcuffs, but not in a fun way. His foolish choice was extremely costly.
Of course, Robinson missed the Super Bowl and the Broncos hammered the Falcons. Hilariously, Robinson won the Bart Starr award on the same day that he solicited the policewoman moonlighting as a hooker. This award celebrates outstanding character and leadership. In the end, Robinson handed the award back because he had made a mockery of it. It’s so ridiculous that if it didn’t really happen, most fans wouldn’t believe it.
Let’s talk about one of the most ill-fated voyages in nautical history. No, we’re not talking about the Titanic or the Lusitania, but instead the Minnesota Vikings’ infamous “Love Boat” incident. It was a fine example of what happens when you have more money than sense. The incident occurred in 2005 when 17 Vikings players had a private boat party on the waters of Lake Minnetonka.
They hired two houseboats as well as about 100 of Atlanta and Florida’s finest women of the night. Soon there were sex acts happening all over the boat in a full few of the watching world. Local police arrived and arrested four players including Vikings’ quarterback Daunte Culpepper and Fred Smoot. Later, the team fired their head coach Mike Tice because his players had no discipline.
One of the most bizarre incidents on this list occurred in 2020 when Ronaldinho decided to sneak into Paraguay. The Brazilian soccer player has one of the most recognizable faces on the planet. The World Cup winner entered the country with his brother using official Paraguayan documents. However, there was one major problem. The information on the identity cards and passports was fake.
In order to qualify for a Paraguayan passport, you need to have lived in the country for a certain amount of time. Police arrested Ronaldinho and his brother before a court placed them under house arrest. However, neither man suffered because they hosted parties during their two-month stay. In sum, this whole story is a weird one. If you’re a mega superstar it’s foolish to use fake IDs.
As a three-time Super Bowl winner with the New England Patriots, Vrabel was extraordinarily successful. With an estimated $11 million in earnings from his playing career, he was flush with cash. Meanwhile, if he went bankrupt for some reason, he could always sell one of his Super Bowl Rings. According to the Sportster, they’re worth between $30,000 and $50,000 dollars, depending on the athlete and the game.
What we are building up to is this: there was no need for Vrabel to steal a couple of bottles of liquor from a deli in 2011. He could have bought the deli if he wanted to. Las Vegas police arrested him for his shenanigans, which he labeled a misunderstanding. They released him on a bond of $600 which was obviously more than the cost of the alcohol. All in all, it was extremely foolish.
You almost have to appreciate Leake’s frugality. The Arizona Diamondback’s pitcher was making just shy of $500,000 a year by 2011. But this didn’t stop him from bargain-hunting, or flat-out stealing. The MLB star went into a Macy’s one day and came out with five $10 t-shirts without paying for them. Why he thought this was a good move, we have no idea.
Leake sneakily removed the tags and tried to walk out of the store, but it didn’t end well for him. Police arrested him and he suffered public humiliation for being a cheapskate. In short, the judge ordered him to complete community service. As a multimillionaire, there was just no excuse for his behavior, and he paid the price for it. It was a very foolish move.
Most of the cases on this list are relatively harmless. However, Hurd’s is one of the most dramatic because he was ready to start a full-blown drug trafficking operation. The former NFL wide receiver received a 15-year prison sentence because he wanted to deal large amounts of cocaine and marijuana. But that’s not why he’s on this list. Hurd divulged his whole plan to an FBI informant.
He came up with the idea during the NFL lockout in 2011 because he obviously wanted to remain constructive. In sum, he wanted to move about 10 kilos of cocaine and a thousand pounds of marijuana around the streets of Chicago every week. Meanwhile, his NFL career ended just like that as he faced up to life in prison. Hurd will enjoy prison hospitality until 2028 because of his choices.
In 2020, Manchester United captain Maguire made headlines for all the wrong reasons after police arrested him in Greece. The UK native was out partying with his friends and ran up a tab of $100,000 from vintage champagne and whiskey. Maguire claimed somebody slipped his sister a ‘date-rape’ drug. Then they somehow got into a fight with undercover police officers.
Meanwhile, the police report claimed that Maguire attempted to bribe the police officers in order to let them go free. However, this only infuriated the police, who left them to stew in a cell for two days. Finally, a court hit Maguire and one of his friends with 18-month suspended sentences. In sum, don’t try and use your celebrity status to get one over the law because you look like an entitled moron.
UK MMA fighter Till is one of the most popular athletes in his sport. He’s an animal in the cage but then he also has a tremendous social media presence. Till is an extremely entertaining personality as can be seen by his exploits in ordinary life. But one of the most foolish moments came when he went on vacation to Spain’s Canary Islands with some of his friends.
Till and his entourage consumed a lot of liquor. This resulted in the group smashing up a hotel room and causing thousands of dollars worth of damage. Then for their coup de grace, they stole their taxi driver’s car. Of course, this was remarkably dumb even if it did entertain the masses. Finally, police arrested Till and his friends. They enjoyed a night in a precinct jail cell.
This is one of the dirtiest crimes on this list and we mean that literally. In 2002, police arrested Davenport after he spent the night with a Barry University student. The Green Bay Packers drafted the University of Miami running back that year and he was back in Florida to party. However, things took a strange turn after the woman, Mary McCarthy reported Davenport’s alleged inappropriate behavior.
She accused him of defecating into a hamper in her bedroom. Police promptly proceeded to arrest him on charges of criminal mischief and burglary. However, Davenport tried to deny the crime by saying, “Where’s the manure?” But he still had to complete community service as penance for the bizarre offense. You’ve got to sympathize with him though because when you have to go, you have to go.
A two-time All-Star and a two-time World Series winner with the Boston Red Sox, Bucholz has had a great career. He also pitched a no-hitter in his second start, which was sensational at the time. However, Bucholz hasn’t always been an outstanding human being. In 2005, he attempted to commit one of the most bizarre crimes of all-time. It was so foolish that it was almost brilliant.
Bucholz was studying at McNeese State University in Louisiana. But they dismissed him after discovering that he had stolen almost 30 laptops from a nearby middle school. Bucholz planned to sell them all on campus but the authorities soon shut him down and he ended up back in community college. However, talent speaks for itself, as he still made his way to the highest level of baseball.
McGregor is no stranger to police hospitality because he can’t stay out of trouble. His many arrests include smashing a fan’s phone because he wouldn’t stop taking pictures of him, alleged sexual assaults, driving offenses, and many others. But when he was in a bar in his native Dublin, he created one of the most foolish situations of them all. ‘The Notorious’ bought a round of shots of his whiskey brand for every patron before the incident went down.
Yet one man in his fifties rejected McGregor’s whiskey and told the former UFC champion in no uncertain terms that he didn’t want it. This annoyed McGregor whose immediate reaction was to punch the older man in the face. Needless to say, this didn’t go down very well because he’s a young professional fighter. In the end, McGregor enjoyed another day in court and paid a hefty fine.
In 2007, Jones went to a strip club with rapper Nelly and some friends because they love good, wholesome fun. The then-Titans’ cornerback got in on the action by helping to make it rain on the stage. They showered the stripper with hundreds of dollar bills but then things turned nasty. Jones didn’t realize that the stripper expected to keep the money. So her decision to gather up the money didn’t amuse him.
Jones had the somewhat extreme reaction of slamming her head against the stage. Things got worse when a shooting incident left a club patron paralyzed. While Jones didn’t pull the trigger, the club manager maintained that he knew the shooter. Later, Las Vegas PD arrested Jones who accepted a plea deal. In sum, he should have just let the stripper pick up the cash. It would have been a lot cheaper.
Now the captain of the Philadelphia Flyers, Giroux makes this list for the strangest of reasons after a bizarre incident in 2014. He was back in Ontario and was in an intoxicated state when he encountered some police officers. Most people would agree that it is best to keep your hands to yourself when you’re interacting with the law. But Giroux had other ideas and proceeded to continuously grope the buttocks of a male cop.
Needless to say, this wasn’t the most popular move that he could have made. Police escorted him to the station where he spent the night in a cell. However, they didn’t press charges after Giroux agreed to donate $20,000 to charity. To grab a police officer’s posterior once is a bold move but to do it twice was simply foolish. Only Giroux knows what he was thinking.
Some exploits are so stupid that they become iconic. That’s exactly what happened in the case of McGregor in 2018. He had a massive rivalry with the UFC lightweight champion Khabib Nurmagamedov. When the Russian and his crew attempted to intimidate McGregor’s teammate Artem Lobov, McGregor decided to react. Khabib was in Brooklyn, New York for UFC 223 so the opportunity was perfect.
The Irishman gathered about 20 of his cronies and flew them by private jet to JFK. From there, they went to Brooklyn’s Barclay Center where they proceeded to storm the arena. Video footage captured McGregor throwing a dolly through the window of a bus containing several fighters including Khabib. Police later arrested the Irishman and he spent the night in a precinct jail cell.
McAfee’s story is lovably foolish. The punter spent eight seasons with the Indianapolis Colts and always had a big personality. However, he had a brush with the law back in October 2010. The outspoken NFL name partied all night in the city before he decided to take a dip in the river. But the intoxicated NFL star didn’t pause to consider how this would look to the good citizens of the neighborhood.
A woman alerted police to the fact that a massive man was walking around dripping wet near her car. They came over to investigate. Firstly, McAfee told them that it had rained. Then they asked him how much he had drunk. After clarifying that he had drunk a lot of alcohol, they brought him to the precinct for the night. Then the Colts suspended him for a game. At the end of the day, it was dumb but harmless.
Arenas is one of the most foolish athletes in the history of humanity. First of all, there was the time that he and Javaris Crittenton pulled guns on each other in the locker room. But that’s not even why he’s on this list. No, we’re talking about another incident that’s almost laughably foolish. In short, if you’re going to carry illegal items in your truck, you should have the brains to drive slowly so as not to attract attention.
However, let’s give him some credit because he was a professional athlete, not a professional criminal. In 2013, police pulled him over for speeding in L.A. But then they proceeded to uncover over 100 pounds of fireworks in his truck. The only thing that could have made this better is if one exploded and the whole truck lit up in different color flames. You almost have to admire his hustle.
Kane is a player who has turned his life around since he was a young man. The Chicago Blackhawks star definitely wasn’t the most mature of individuals when he was young. In sum, he once punched a taxi driver for the grievous offense of short-changing him. Remember that Kane is worth millions of dollars from a number of lucrative contracts. But at the age of 20, he wasn’t taking anything for granted.
We’re literally talking about 20 cents here but for Kane, it was a matter of principle. In his drunken state, he believed a tip wasn’t something that a person should take. Instead, you should make it clear that you’re giving it to the person. So he reacted violently when the driver didn’t have enough change for him. Then he ended up in a police cell on assault charges. That’s how the cookie crumbles.
New York has some of the strictest gun laws in the entire United States. Unfortunately, nobody told former Giants wide receiver Burress, who committed one of the most foolish crimes in the history of mankind. First of all, it’s a risk to possess an unlicensed weapon in that state so you would have to be extremely confident or dumb to bring it out in public. However, Burress accidentally shot himself in the groin with his handgun in a nightclub.
The former star faced the full brunt of the law and spent 20 months in jail for his action. Meanwhile, the Giants tried to avoid paying him his one-million-dollar signing fee. However, a court of arbitration forced against their wishes. But after serving his time, he returned to the NFL where he won the Comeback Player of the Year award. What a story it is.