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What are the most recent 10 Big Celebrity Gambling Losses?

You know the old expression “youth is wasted on the young”? Well, all too often is wealth wasted on the rich. And nowhere can this be more properly seen than from a list of 10 Big Celebrity Gambling Losses; the average person – and particularly the average casual casino-goer – may feel outraged at the way the rich and powerful and able to play at the finest gambling houses in the world in the most comfortable of settings, with the most exquisite of services, only to ultimately lose that privilege due to excessive and frequent bad judgment.

Many of those enumerated on this list of shame have gotten help for a gambling problem, but many more of the glitterati are stupidly throwing away money that they may not deserve to have. Check out the following stories and use them as warnings if you can, but for most of us plebes, it’s hard to imagine having this much dough to spend…

•  Charlie Sheen. You knew that Charlie was doing a lot of cocaine while on an interestingly self-destructive path in the 2000s, but have you heard about his gambling debts? According to documents from his divorce proceeding with Denise Richards in 2006, Sheen had reportedly been spending a whopping $200,000 a week on sports betting. It is unclear whether Sheen at this point thought he was actually “Wild Thing” Vaughan. Also unclear is whether he’s still wagering on sports; somehow the guy’s still finding work, so the money is there…

Total losses: $200,000 a week equals over $2.5 million in three months, so that’s probably the floor for any estimation…

•  Gladys Knight went from status of the “Empress of Soul” to Gamblers Anonymous cautionary tale due to after her self-assessed $40,000 per night addiction to casino table games such as blackjack and baccarat plus a fondness for sports betting. Straight through to her retirement in the early 2000s, Knight was involved with numerous R&B hits consistently – but she was always hiding her addiction. As she describes plainly in her autobiography, “I would play every day if I could.” Surely she kept busy enough with touring and recording projects, but just as surely did she lose millions.

While she has never publicly estimated or disclosed her total losses, just 25 trips with her reported typical $40,000 bankroll equals $1 million; 90 trips (or every day for three months) would equal $3.6 million. This doesn’t figure in the sports betting, and years she played. Total losses: impossible to say; perhaps between $2 million and $6 million.

Is there a connection between Professional Basketball and Gambling?

basketball player and big gambler michael jordan•  Michael Jordan is a master at image control and maintaining his privacy, but everyone recalls the stories from Richard Esquinas’s book Michael & Me: Our Gambling Addiction … My Cry For Help! in which Jordan would habitually have $1 million at stake in a single golf game, betting $100,000 or $250,000 per putt. Former Chicago Bulls player Jay Williams recounts tales of MJ betting $100,000 on rock/paper/scissors.

In the mid- to late 1990s, Jordan himself claimed he was pulling in $150 million a year. So how much do *you* suppose he dropped on games of chance per year? One is tempted to calculate starting with the open and honest assessment by his Dream Team teammate Charles Barkley (see below) and add in Jordan’s much higher salary, but unlike Barkley, Jordan seems to eschew casino gaming and wager copious amount on unorthodox proposition bets. Total losses: impossible to say.

hoops player charles barkley gambler and hall of famer•  Charles Barkley. The NBA Hall of Famer and current NBA analyst has admitted to blowing lots of money at casinos, with six-figure binges common since his playing days with the Philadelphia (just about 65 miles from Atlantic City!) 76ers. This topic has come up within some of the utterly uncountable interviews and TV appearances he’s put in since retiring from the NBA. In 2006, Barkley acknowledged the problem in an interview with ESPN, but wasn’t quite as contrite as some no doubt would have hoped:

Yeah, I do have a gambling problem but I don’t consider it a problem because I can afford to gamble. It’s just a stupid habit that I’ve got to get under control, because it’s just not a good thing to be broke after all of these years.

Nine years later, he’d changed his tune, telling Campus Insiders that his problem was “getting out of control” before he’d recently quit playing. “I went to Vegas a bunch of times and won a million dollars. Probably 10 times. But I've also went to Vegas and lost a million probably three times as much,” he explained

Total losses: In ’06, the outrageously honest Sir Charles stated he’d lost $10 million. According to his story above, however, that number is at least $20 million.

So in total, the four above-listed celebrities have lost at least $25 million plus whatever Jordan threw away. And it makes perfect sense: As high-level entertainers and athletes, folks like Gladys Knight and Charles Barkley earn frankly obscene amounts of money, thus providing more disposable income than the everyday joe knows what to do with.

But every time, thinking of the amounts our 21st-century jesters make irks you, remember this: Some are higher up the food chain than this bunch – think studio heads, sports franchise owners, CEOs. This strata is composed of the proverbial one percent, with multiples of times more wealth and usually well less accountable for their trespasses – until a habit like excessive gambling forces them to reckon with truth. For example, check out a guy like…

Big gambling losses are not limited to the professional athletes, musicians and actors

acclaimed producer and big gambler david milch •  David Milch, who has four Emmy awards on his shelves – if he still has shelves. After ruling Burbank as a producer on three decades’ worth of successful series, including Hill Street Blues, L.A. Law, NYPD Blue and Deadwood. Mills jacked away a reported $100 million he’d accrued from the work by 2011, however, when he’d run up $17 million in debt after losing $25 million in various gambling pursuits. Stunningly, his wife has not divorced him and as of 2015 had engaged legal representation to sue her husband’s former business managers who’d allowed him to lose so much. Total losses: At least $25 million from 2000 to 2011.

• Former San Diego Mayor Maureen O’Connor started as a humble high school teacher to marry into billions and become her city’s first-ever female mayor – and was ultimately taken down by her gambling habits. After marrying Jack In The Box founder Robert Peterson in 1977, O’Connor worked her way up San Diego’s political ladder with Peterson’s support to serve as mayor from 1986 to 1992. Peterson died in ’94, and O’Connor’s addiction problem probably festered shortly thereafter.

Though staying fairly active in local politics after her mayoral term, she grabbed the biggest headlines in 2013 for her role in a money-laundering scam within which she pilfered some $2 million from a nonprofit organization she managed. In the courtroom, prosecuting attorneys claimed that O’Connor had wagered an insane $1 *billion* in just eight years and that she’d lost $13 million, enough to sink her financially and cause her to turn to crime. Total losses: At least $13 million.

• While O’Connor went from rags to riches to rags, Leonard Tose only needed to complete the last two bits of the equation, blowing an estimated (estimated!) $50 million of his trucking-industry fortune in casinos, approximately $20 million and $14 million alone going into Atlantic City’s Resorts International and the Sands Casino, respectively – more than double the amount he’d bought the Philadelphia Eagles NFL franchise in 1969. He divested his ownership of the Eagles in 1985 to pay off a $25 million debt; thereafter, two of his homes were seized for unpaid taxes and Tose died in 2003 with little more than pleas to official committees about problem gambling.

Total losses: As much as $50 million. (In a slightly overwrought Newsday piece of 1993, Tose also laments that he lost his “pride and dignity” along with his millions, but we can’t quantify that here.)

•  Kerry Packer, a UK media mogul once legendarily went on a three-week casino binge in which he lost £15 million, but a further legendary story has Packer dropping £15 million on *three spins* of the roulette wheel. Perhaps he was seeking to best his peer Robert Maxwell, also a fat cat in the UK media biz, who once lost £1.5 million in three minutes by playing three roulette wheels simultaneously.

•  And then there’s Harry Kakavas, an Australian real estate industry giant who habitually played casino card games for $300,000 a hand and once went on a 5½-hour losing streak which cost him AU $164 million.

And the number one spot for biggest Celebrity gamblings losses is.........

celebrity gambler and big drinker Terrance Watanabe•  Finally, let’s talk about Terrance Watanabe, the rare case of a guy who became a celebrity *because of* his extreme gambling losses. While well-known among high-end casinos worldwide for years, the Nebraska-based business made international mainstream news in 2007 when it was revealed that he’d lost an incredible $127 million in one year at just two Las Vegas casinos: the Rio and Caesars Palace. The revelation came out in a court case over some $14 million of that debt still outstanding; within the case, Watanabe’s attorneys argued that their client’s poor gambling skills were exacerbated by casino employees, who were plying the man with up to three bottles of vodka daily. Total losses: $127 million.

The moral of these stories? Please gamble responsibly: gambling may be fun, but every pleasure has its natural limits.

Also, appreciate the money you do have; most of us don’t have the leeway of millionaires and billionaires…