7 Athletes Who Went Directly To Jail

Getty Images
Getty Images

It's been a rough week for former NFL players on the judicial circuit. O.J. Simpson couldn't beat a robbery and kidnapping charge and now faces life in prison. Former first-round bust running back Lawrence Phillips got slapped with a 10-year prison sentence following his own checkered career on the wrong side of the law. These sentences may come as a surprise to cynical fans who think there's no way a famous athlete could end up in prison, but sports figures serving hard time isn't exactly uncommon. Here are seven who did not pass go, did not collect their $200, and went directly to jail.

1. Craig MacTavish

As an NHL player, MacTavish was a solid center who enjoyed a long career that spanned from 1979 to 1997. He even won four Stanley Cups. However, he missed the entire 1984-85 season because he was incarcerated. MacTavish had been driving drunk on January 25, 1984, when he was in a wreck that killed a 26-year-old woman. MacTavish was found guilty of vehicular homicide and spent a year in jail before resuming his career. He's currently the head coach of the Edmonton Oilers.

2. Rae Carruth

Perhaps the most infamous of all NFL players, Rae Carruth's career as a wide receiver for the Carolina Panthers actually got off to a promising start. During his rookie season in 1997, he caught 44 passes, including four touchdowns, and made the NFL's all-rookie squad. In 1999, though, everything unraveled for him. His pregnant girlfriend was caught in a drive-by shooting. Despite four shots being fired in the car, she managed to call 911 and describe Carruth's role in the assault. The receiver apparently blocked her car while a shooter in a separate car fired the shots. Carruth posted $3 million bail, but after his girlfriend died, he took off. He was eventually found in Tennessee, hiding in the trunk of a car with a huge pile of cash, some snacks, and a bottle to hold his urine. He's currently serving no less than 18 years, 11 months in prison following a conviction for conspiracy to commit first-degree murder.

3. Ugueth Urbina

Baseball fans remember Urbina as a solid right-handed reliever with a nice fastball/slider combo that helped the Florida Marlins win the World Series in 2003. Fans of Venezuelan jurisprudence remember Urbina as the man behind a horrific assault. Urbina was convicted of attempted murder in 2007 following an incident in which he allegedly attacked five workers on his Venezuelan farm with a machete and then tried to douse them in gasoline. Urbina maintains that he was asleep during the attack and that he is innocent. Nevertheless, he received convictions for attempted murder, illegal deprivation of liberty, and violating a Venezuelan law that prohibits taking justice into your own hands. He's serving a 14-year prison term.

4. Mike Danton

Lowly players have been known to run afoul of the law, too. Take Mike Danton, a fairly low-level NHL center who played for the New Jersey Devils and St. Louis Blues. Danton racked up 141 penalty minutes during the 2003-04 season, but off the ice he didn't do his own dirty work. When he wanted his agent, David Frost, dead in 2004, he didn't want to get his own hands dirty. Instead, he tried to hire a hitman to do the job for him. Unfortunately for Danton, his "hitman" was actually a police dispatcher. Danton pled guilty to conspiracy to commit murder and is currently serving a 90-month term in federal prison.

5. Denny McLain

Denny McLain's career as a Major League pitcher was brilliant. He won two Cy Young awards, an American League MVP award, and a World Series ring during a career that ran from 1963 to 1972. He's still mentioned on baseball broadcasts as the last man to win 30 games in a season. McLain wasn't quite a masterful off the field, though. He had a penchant for gambling, which led him to make underworld connections and even run his own bookmaking operation. These troubles eventually led to the end of his baseball career, at which point McLain veered further afoul of the law. He worked for a Florida financial services company with rumored Mob ties, which led to a 1985 conviction for racketeering, extortion, and drug trafficking. He spent a couple of years in jail on that charge, and then bought a Michigan meat-processing plant in 1994. Two years later the plant went bankrupt, and McLain and his partner were charged with looting $12.5 million from the company's pension fund. McLain spent six years in federal prison for the theft and was released in 2003.

6. Darryl Henley

Darryl Henley was enjoying a nice career as a starting cornerback for the Los Angeles Rams until 1995, when he was convicted for cocaine trafficking. He received a 20-year sentence for those charges, which quickly ended his NFL career. He made things worse for himself by then attempting to hire a hitman to murder his ex-girlfriend—a former Rams cheerleader and a witness in the trial—and the judge. His sentence then ballooned to 41 years, and he won't be eligible for parole until he's 65 years old. To his credit, Henley has realized the error of his ways and now runs a website and charity to try to help other athletes from falling victim to the same forces that brought him down.

7. Don King

Don King may be known for his trademark fright-wig hair and his inimitable diction, but before he became boxing's most powerful promoter, he served time. In fact, he killed two different men before his rise to fame. The first case was judged justifiable homicide; King shot a man who had attempted to rob the illegal bookmaking joint he ran. The second killing, though, occurred when King beat to death an employee who owed him money. King was convicted of second-degree murder for this killing, but the charges were later reduced to manslaughter. He ended up spending around four years in jail for the killing.

Ethan Trex co-writes Straight Cash, Homey, the Internet's undisputed top source for pictures of people in Ryan Leaf jerseys. He is aware of both Mike Tyson and Michael Vick and their troubles with the law.

See also...

A Brief History of Stadium Naming Rights
*
How Sports Owners Made Their Money
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10 Bizarre Athlete Superstitions
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7 Famous Athletes Who Now Sell Food
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The Bud Bowl: A Definitive History
*
Quiz: Mr. Burns' Softball All-Stars

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From Ear to Eternity: When Mike Tyson Bit Evander Holyfield

Evander Holyfield (L) and Mike Tyson (R) compete in their rematch in Las Vegas on June 28, 1997. The bout would make sports history.
Evander Holyfield (L) and Mike Tyson (R) compete in their rematch in Las Vegas on June 28, 1997. The bout would make sports history.
Focus On Sport/Getty Images

As the 16,000 spectators began filing out of the MGM Grand Garden Arena in Las Vegas, Nevada, following a night of fights on June 28, 1997, MGM employee Mitch Libonati noticed something strange on the floor of the boxing ring. He later described it as being roughly the size of a fingernail, with the texture of a piece of hot dog or sausage.

It was no concession stand remnant. It was a piece of Evander Holyfield’s ear.

Wrapping the morsel of flesh in a latex glove, Libonati hurried backstage, where Holyfield was conferring with officials and doctors after his opponent, Mike Tyson, had been disqualified for biting him on the left ear. In all the commotion, Libonati wasn't allowed inside the room. But Michael Grant, one of Holyfield’s training partners, accepted the ear fragment on Holyfield’s behalf.

Libonati’s discovery was the climax to one of boxing’s most controversial and bizarre evenings, one in which "Iron" Mike Tyson—the most famous fighter of his era—meted out a savage reprimand for what he perceived was dirty fighting on the part of Holyfield. The ear-biting far exceeded the brutal underpinnings of boxing and added to Tyson's reputation as a frenzied combatant both in and out of the ring.

 

Mike Tyson’s collision with Evander Holyfield had started when the two were just teenagers. On the amateur circuit, they had sparred together—not quite knowing the heights each would achieve, but understanding the other would be a formidable obstacle if they were to ever meet as professionals.

Evander Holyfield (L) had success against Mike Tyson (R) early on.Focus On Sport/Getty Images

Tyson was a prodigy, having won the heavyweight championship of the world in 1986 at the age of 19 and dominating the division up until an upset loss to James “Buster” Douglas in Tokyo, Japan, in 1990. Holyfield was the lighter fighter at cruiserweight (190 pounds), moving up to the heavyweight division in 1988 and gaining respect for his trilogy with Riddick Bowe.

Long before that fateful night in 1997, Tyson's personal life had started to overshadow his accomplishments inside the ring: An allegedly abusive marriage to actress Robin Givens darkened his image in the media and ended in a very public divorce after just one year. In 1992, a rape conviction sidelined the fighter for more than three years while he served out his prison sentence.

When Tyson returned to the ring, he rattled off a string of wins against fighters not quite at his level, including Peter McNeeley, Buster Mathis Jr., Frank Bruno, and Bruce Seldon. Holyfield had stepped away from competition in 1994, but as Tyson knocked off inferior opponents, talk of a bout with Holyfield intensified. Finally, the two met in Las Vegas on November 9, 1996, with Tyson a 17-1 favorite over the semi-retired Holyfield.

Holyfield would prove his doubters wrong. Through 11 rounds of action, he outmaneuvered and outclassed Tyson by negating his opponent's power with movement and volume. Holyfield also landed headbutts that were declared unintentional, but to Tyson seemed deliberate. Before the fight could see a 12th round, Holyfield knocked Tyson down and earned a technical knockout victory.

 

While it was an undoubtedly disappointing moment for Tyson, an upset in boxing virtually guarantees a lucrative rematch deal. Both men agreed to meet a second time, with Holyfield earning $35 million and Tyson getting $30 million. Tyson’s camp, however, insisted that the referee from the first bout, Mitch Halpern, not be booked for the second, because Tyson felt he failed to call the illegal headbutts. The Nevada State Athletic Commission didn’t want to be seen capitulating to Tyson’s demands, but Halpern stepped aside voluntarily. So referee Mills Lane took his place.

Evander Holyfield (L) and Mike Tyson (R) first met as amateurs.Focus On Sport/Getty Images

Before a huge crowd full of A-list celebrities like Sylvester Stallone and a then-record 1.99 million households that had purchased the event on pay-per-view, Tyson and Holyfield met for a second time at the MGM Grand Garden Arena on June 28, 1997. While Holyfield took the first round, Tyson appeared fit and adaptive, and came out blazing in round two. Then, just as Tyson had feared, Holyfield’s headbutt struck him again.

The clash of heads opened a cut over Tyson’s right eye, which threatened to obscure his vision as the fight went on. It also opened a reservoir of frustration in the fighter that would manifest in a spectacularly violent way.

Coming out for the third round, Tyson had forgotten his mouthpiece and had to go back and retrieve it—a foreshadowing of things to come. His aggression was working against Holyfield, but with 40 seconds left in the round, the two clinched up. Tyson moved his mouth so it was near Holyfield’s right ear. With his mouthpiece still in place, he clamped down on the ear, ripped the top off, and spat it along with his mouthguard onto the canvas.

Holyfield jumped up in the air in shock and pain. Referee Mills Lane was initially confused by what had happened until Holyfield’s trainers, Don Turner and Tommy Brooks, yelled out what Tyson had done. Lane called for a doctor then told Marc Ratner, the executive director of the athletic commission, that he was going to end the fight. Ratner asked if he was sure. Seeing Holyfield was bleeding from his ear but otherwise ready to fight, Lane waved the two men back into competition.

Incredibly, Tyson bit Holyfield a second time, this time on the left ear, before the round ended. This time, Lane was aware of what was happening and had seen enough. Before the start of the fourth round, he disqualified Tyson.

 

That was far from the end of it. Realizing he had lost the fight, Tyson grew incensed, shoving Holyfield from behind and pawing at the security guards who had stormed the ring in an attempt to restore order.

After the bout, Tyson didn’t appear to be overly contrite. He explained that he was frustrated at Holyfield headbutting him without being penalized, and said he had lost control.

An emotional Mike Tyson reacts to his disqualification loss to Evander Holyfield.Focus On Sport/Getty Images

“Listen,” Tyson said. “Holyfield is not the tough warrior everyone says he is. He got a nick on his ear and he quit.”

Tyson believed his retaliation was justified. “This is my career," he said. "I’ve got children to raise and this guy keeps butting me, trying to cut me and get me stopped on cuts. I’ve got to retaliate. What else could I do? He didn’t want to fight. I’m ready to fight right now. Regardless of what I did, he’s been butting me for two fights. I got one eye. He’s not impaired. He’s got ears. I’ve got to go home and my kids will be scared of me. Look at me, look at me, look at me!”

Two days later, Tyson issued a tempered apology in an effort to minimize the consequences, but it was too late. In addition to losing his boxing license in the state of Nevada, Tyson was fined 10 percent of his purse, or $3 million, which was thought to be the largest fine in sports at the time.

 

Tyson could never entirely shake the stigma of his actions. When a lucrative bout with Lennox Lewis was being planned in 2002, the fight ultimately ended up taking place in Memphis, Tennessee; Nevada refused to restore Tyson's license following a press conference brawl between the two men.

Tyson ultimately continued competing through 2005, when he lost his last bout to Kevin McBride. Holyfield retired in 2011. Earlier this year, the 54-year-old Tyson expressed a desire to return to the ring. The fighter once known as "The Baddest Man on the Planet" is scheduled to fight Roy Jones Jr. on November 28, 2020. Yet Holyfield, now 57 years old, remains a possible future opponent.

The two have occasionally interacted in public in interviews, with Tyson expressing remorse and Holyfield admitting he briefly thought about biting Tyson on his face right back. The pair even filmed a spot for Foot Locker in which Tyson “gave” Holyfield the missing piece of his ear.

In reality, Holyfield never did get his ear back. After Mitch Libonati handed it over to Michael Grant, the piece somehow fell out of the latex glove while being transported to the hospital.

Many fighters talk about leaving a little piece of themselves in the ring. It’s usually metaphorical. For Evander Holyfield, it was simply the truth.