Question of the Day - 20 November 2025

Terry Watanabe is another in a long long LONG line of accursed game players who, for one reason or another, incurred the wrath of the gambling gods -- by way of the Las Vegas casinos.

As we saw in the previous QoD, at the end of his casino spree in 2007, he'd wagered $825 million and lost somewhere in the neighborhood of $130 million to $350 million. The total has never been confirmed, but we do know that he set the record for losses in one year; no one else before or since lost that much money in a single 12-month period in Las Vegas history. 

His money came from the family business. His father Harry emigrated from Japan in the 1930s and started the Oriental Trading Company in Omaha, sellling knickknacks imported from Nippon. He quickly expanded to nearly 20 locations throughout the Midwest, but had to close all but the original one in Nebraska when World War II interrupted the whole thing. After the war, Oriental recovered and started to grow in earnest. 

Terrance was the oldest son, born in 1957, and started working around the business even before he attended kindergarten. He continued moving up the company ladder and took over as CEO when he was only 20 years old. He quickly expanded Oriental, perfecting direct-mail marketing and turning it into one of the biggest mail-order party-supply companies in the country. In just under 25 years, he sold Oriental to a Los Angeles-based private-equity firm for an undisclosed amount of money, but considering what happened next, it had to be in the hundreds of millions.   

Left adrift around age 45, Watanabe succumbed to the TMTaM (Too Much Time and Money) Syndrome. He bought an 18,000-square-foot house in Omaha, donated millions to charities, and took up a new hobby, table games, at Harrah's Council Bluffs, just across the Missouri River from Omaha in Iowa. From there, Watanabe discovered Las Vegas and within only a couple of years, he was essentially a captive of the place. 

As one account put it, he was the quintessential whale. "He wasn't flashy. He didn't come with an entourage. He didn't demand attention. But what he lacked in theatrics, he made up for with a willingness to bet — and lose — more money, more quickly, than anyone the casinos had ever seen. Rotating from the Wynn and Caesars Palace to the Rio, he was quiet, generous, and dangerous to himself — the perfect high roller."

Steve Wynn himself reportedly became concerned that Watanabe was caught up in at least two addictions -- gambling and alcohol -- and banned him from the property, worried about lawsuits stemming from dealing to a seriously inebriated degenerate high-stakes gambler. 

But Caesars has a long long LONG history of catering to exactly these kind of people and this time, once again, they were only too happy to indulge Watanabe with perks that raised the eyebrows of even the biggest whales of the day, including, by Watanabe's own account, prescription painkillers. 

Watanabe was also George on steroids, handing out $100,000 Tiffany gift cards to dealers, paying off pit bosses' mortgages, tossing $25,000 chips to random strangers in elevators. In one famous incident, he paid a local In N Out $50,000 to open at three in the morning and provide hamburgers and fries to the entire graveyard shift at Caesars. 

At the tables, Watanabe was obviously impaired, mixing booze and opioids. Meanwhile, Caesars kept raising his betting limits and increasing his credit line. They claimed they had no idea that anything might be amiss with this falling-down drunk. (Same as they claimed to have no idea where Brian Molony, a mild-mannered Canadian assistant bank manager, might be coming up with the $10 million that he embezzled and lost over a 14-month period in 1982-1983.)

Finally, his sister came to visit Watanabe in Las Vegas over Thanksgiving 2007 and when she saw what was happening, she packed his bags and dragged him away from Vegas, never to return. 

In 2009, Watanabe sued Harrah's Entertainment, accusing the company of enabling his addictions and downfall. Harrah's countersued, claiming Watanabe owed them nearly $15 million in upaid markers. The Clark County DA piled on, charging him with four felonies (one for each marker; as we know, the DA's office earns a 10% commission on collections). 

In the end, the criminal charges were dropped and Watanabe and Harrah's negotiated a confidential settlement. 

Today, by his own admission, Terrance Watanabe lives on Social Security.