The blackjack tables have been the setting of some of gambling’s most historic losing streaks.

We love to hear about a big winner. In 2011 Don Johnson captured the gambling world’s attention by winning $15 million at Atlantic City blackjack tables over a span of six months. His fantastic run included taking $6 million at the Tropicana during a six-hour run, costing the company’s CEO his job. He also won $5 million at the Borgata and $4 million at Caesar’s and is now banned from every casino in the city.

As much as we enjoy a feel-good success story, however, something about downfall is irresistible. Owing to some dark part of human nature most of us get more pleasure watching tragedy than triumph. That is why the most sensational casino stories concern losing streaks, not winning streaks. This piece will travel through time, recounting some of the most epic collapses in blackjack history.

Kerry Packer blows $1 million daily

Australian billionaire Kerry Packer was often called the “greatest gambler in the world.” He once lost $20 million in 2000 during a three-week string of losses at the Bellagio. This is the second-worst three-week loss in casino history (Archie Karas lost $40 million over the same amount of time playing poker and craps). Packer wasn’t a completely useless gambler; he also ran up huge winning streaks, sometimes winning millions at the blackjack table in a single night.

During his epic cold streak at the Bellagio Packer lost on average $1 million per day, most of it on blackjack. His favorite blackjack strategy was placing $300,000 bets on each individual hand. Some say that this is the highest number ever wagered on a single hand in Vegas history. Despite losing so many of these he just wouldn’t leave the table; casino staff, friends and business partners recall that nothing enflamed his passions more than gambling, and he took losses surprisingly well.

Packer’s $6.5 billion fortune meant that he could bring a bottomless bankroll into any casino and losses meant nothing to him. While he proved to be a big loser at times, casino managers were nonetheless nervous any time he came through the doors. Legend has it that he personally forced the Aspinall Casino in London into bankruptcy by winning so much at the blackjack tables.

Omar Siddiqui loses $167 million of embezzled cash

Electronics executive Omar Sidduiqi’s $200,000 wagers may look like child’s play in comparison to Packer’s massive bets, but his story is the stuff of legend. The big-wig at Fry’s Electronics in California hatched a brilliant scheme to illegally extract commissions (“kickbacks”) from the retailer’s wholesale providers, in turn using the money to finance his gambling addiction.

Siddiqui would make regular trips to Vegas with his ill-gotten cash and place huge bets on his game of choice: blackjack. Not only did he love gambling, he was very bad at it. In fact casinos so much enjoyed taking his money that they would fly him in on private jets. It is estimated that from 1999 to 2009 Siddiqui lost $167 million in various Vegas casinos. It has even been reported that he once blew $8 million at the blackjack tables in a single day.

In the end, it wasn’t losing blackjack strategies that sunk him. It was the Internal Revenue Service. In 2008 a colleague caught wind of his scheme and reported him to the tax authorities, who began taking a look at his untaxed income from kickbacks. He is now facing federal fraud charges and is being sued by seven different Vegas casinos for unpaid debts of roughly $33 million.

Terry Watanabe’s tragic losing streak in blackjack

The previous stories were sensational but nothing in comparison to that of Terry Watanabe, who is doubtless the biggest blackjack loser of all time. In 2000 Watanabe, the son of a fabulously wealthy American entrepreneur, sold the family empire to a private equity firm. Rather than put his personal fortune to good use he took it to Vegas. He began gambling in 2003 and starting making regular trips to Vegas in 2005, turning his fortune into dust in only a few years. Watanabe descended into incontrollable gambling addiction, which numerous observers say was encouraged by the accommodative behavior of casino managers.

Watanabe lost an unspeakable $127 million in a single year, 2007. It is reported that he personally provided 5.6 percent of Harrah’s Las Vegas revenue that year. He was known to frequent the blackjack tables at the Rio and Caesar’s Palace (both owned by Harrah’s), often placing outrageous bets while exhausted and visibly intoxicated. Watanabe has sued Harrah’s to cancel some of his gambling debts on grounds that casino staff regularly supplied him with alcohol and painkillers to keep him playing, and playing poorly.

Watanabe’s losses were epic. He was known to spend 24 hours uninterruptedly at a blackjack table, once losing $5 million in a single day. Harrah’s staff allowed him to play three blackjack hands simultaneously (which is prohibited at most casinos) and the casino extended him a $17 million line of credit. While Vegas casinos are dependent on the losses of high-rollers to turn a profit each year, the case of Watanabe is a tragic and clear case of shamefully exploiting someone’s gambling addiction.