Terrance Watanabe Lost More Money In Vegas In A Single Year Than Anyone In History ($204 MILLION!). He Now Lives On Social Security

At around 3 a.m. one night in Las Vegas, Terrance Watanabe got a craving for In-N-Out Burger. The problem? It was closed. Most people in this situation would stumble back to their hotel for a late-night room service burger. Not Terrance Watanabe. Determined to get his Double-Double, Terrance offered the staff $50,000 to reopen the restaurant just for him — and to cook enough burgers for the casino dealers working his table. They did.

That kind of move wasn't unusual when Watanabe was in town. The Nebraska-born businessman became the center of gravity in any casino he entered. He was soft-spoken, polite, and obscenely generous — a man who handed out $25,000 chips to strangers in elevators, tipped millions, and regularly turned the most extravagant VIP offerings into something that still wasn't quite enough.

At his peak in 2007, Terrance personally wagered $825 MILLION. By the end of that year, Terrance had lost more money in a single year than anyone in Las Vegas history.

Behind the private jets, the penthouse suites, the seven-course meals served at the blackjack table, and the surreal spending sprees was a man in the throes of addiction — to gambling, to alcohol, to opioids — and to the feeling of being someone in a city that rewards excess.

Once worth hundreds of millions of dollars, today Terrance has no money and lives on Social Security… and he just gave his first interview ever…

First Interview Ever

Long-time CelebrityNetWorth readers probably recognize Terrance's story because we've referenced it a number of times in various articles. His net worth profile page trends every few months when his story is retold by a big account on TikTok or Twitter. However! Last week, Terrance gave his FIRST interview ever.

Terrance sat down with a YouTube channel called WagerTalk TV. In the interview, Terrance told his story for the first time outside of a courtroom and dropped some bombshell revelations no one previously knew. For example, Terrance revealed for the first time that at the height of his gambling, he was suffering from an undiagnosed bipolar disorder. He also revealed that his gambling losses were even larger than had been reported before. I'll embed the interview at the end of this article. I would embed it here, but the thumbnail gives away one of the biggest new bombshells. For now, let's back up a minute and explain how Terrance even came to have hundreds of millions of dollars to gamble with in the first place…

A Billion-Dollar Plastic Trinket Fortune

Terrance was born in 1957, the eldest son of Harry Watanabe, a Japanese immigrant who founded Oriental Trading Company. What began as a modest gift shop selling novelties and trinkets eventually grew into one of the largest mail-order party supply businesses in the country. Harry founded Oriental Trading in Omaha, Nebraska, in 1932 and soon expanded to 17 stores throughout the Midwest. Unfortunately, during World War II, he was forced to close all but the original Nebraska location when Japanese import restrictions hit the company hard. Imports resumed in 1954, and the company launched its first catalog in 1956.

Like many first-generation business families, the Watanabes lived and breathed the company. Terrance started helping out when he was just five years old — sweeping floors, sorting inventory, and watching closely as his father ran the operation. By his teenage years, it was assumed he would one day take over.

In 1977, at just 20 years old, Terrance was named CEO. He set about expanding the company's catalog and distribution, embracing the early wave of direct-mail retail marketing. Under his leadership, Oriental Trading exploded in scale — serving schools, churches, nonprofits, and event planners nationwide.

In 2000, Watanabe orchestrated the sale of Oriental Trading to a Los Angeles-based private equity firm called Brentwood Associates. The exact price was not disclosed, but it was large enough for Terrance to walk away with hundreds of millions of dollars in liquid cash.

In 2006, Brentwood Associates sold the company to a private equity firm called Carlyle Group for $1 billion. Perhaps as a result of the 2008 economic downturn, Oriental Trading went bankrupt in 2010. In 2011, it was acquired by yet another private equity firm, KKR, for $250 million. And a year later, KKR flipped the business to Warren Buffett's Berkshire Hathaway for $500 million. In 2013, Berkshire acquired a toy maker called MindWare and subsequently placed the rebranded "OTC Direct Inc." under the MindWare umbrella.

But let's get back to Terrance. In 2007, he walked away from the family business with hundreds of millions of dollars and no clear plan for what came next. In public, he said he wanted to focus on philanthropy and "have more fun." Privately, the structure that had defined his life since childhood was gone — and with it, the purpose that had kept his most self-destructive impulses in check.

Terry Watanabe in 1995 (copyright Omaha World-Herald)

A Dangerous New Pastime

With his fortune secured and no more business to run, Terrance Watanabe found himself with an abundance of time, money, and restlessness. For a man who had spent decades micromanaging product lines and warehouse operations, early retirement was disorienting. He donated millions to AIDS research and Omaha-based charities, and he purchased a sprawling 18,000-square-foot mansion in one of the city's wealthiest neighborhoods. But without the day-to-day demands of work, he began searching for distraction — and found it just across the river.

In Council Bluffs, Iowa, a short drive from Omaha, Harrah's Casino offered just enough noise and neon to keep his mind occupied. At first, gambling was simply a novelty — a way to kill a few hours, like taking up golf. But it didn't stay casual for long. The staff took notice of his spending early, and Watanabe quickly became one of their most valued guests.

By 2003, the local casino wasn't just a diversion — it was a routine. Dealers knew his name. Hosts ensured his favorite games and drinks were always ready. He played blackjack and roulette, but mostly he liked to be in action, to feel the stakes. The line between "fun" and "compulsion" blurred fast.

Soon, Council Bluffs wasn't enough.

Welcome to Las Vegas

When Terrance Watanabe first began visiting Las Vegas in the early 2000s, casino executives didn't yet realize what had walked through their doors. 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 they'd ever seen.

What started as sporadic trips soon became a near-permanent residency. By 2005, Watanabe was essentially living full-time in Vegas, rotating between the Wynn, Caesars Palace, and the Rio. He was quiet, generous, and dangerous to himself — the perfect high roller. The perfect whale.

At first, he settled into the Wynn, where his behavior eventually caught the attention of owner Steve Wynn himself. After a few private conversations, Wynn reportedly became concerned that Watanabe was both an alcoholic and a compulsive gambler. In a rare move, he banned him from the property entirely — fearing regulatory consequences if the casino continued allowing him to play while visibly intoxicated.

But Las Vegas is not a one-casino town. And what Wynn rejected, Harrah's Entertainment (now Caesars Entertainment) eagerly embraced.

Watanabe was welcomed back to Harrah's with open arms and unprecedented perks, including:

• A three-bedroom suite
• $500,000 line of credit in gift shops
• $12,500 monthly for airfare
• 15% cash back on large table-game losses.
• He was given a custom brand of Russian vodka, flown in just for him, and attended by a rotating staff of casino-provided assistants and security.

He didn't just gamble. He moved in.

Keep Him Gambling

At Caesars and the Rio, Terrance Watanabe wasn't just a guest — he was the house's golden goose. Casino executives knew his face. Staff were told to make him happy at all costs. His photo was reportedly posted in employee backrooms with a clear message: keep him gambling.

And he did. For hours. Sometimes for 24 hours straight.

Watanabe would regularly play three blackjack hands at once, each with a $50,000 limit. His games were catered affairs — gourmet meals delivered to the table, servers bringing his favorite drinks, bodyguards posted nearby. Over time, his line of credit ballooned to $17 million, and he was given near-unlimited access to the highest-limit tables on the Strip.

But as the bets grew, so did the darkness underneath them.

As just revealed in his first-ever interview, the casino staff didn't just serve him drinks — they allegedly provided him with prescription painkillers like Lortabs, often in bulk. His personal security team, assigned by the casino, was said to help prepare cocaine and deliver pills at his request. One host even allegedly handed him a box of opioids as a "gift" after he slipped and injured himself in the shower.

By that point, Watanabe wasn't just gambling. He was spiraling — in full view of the very people profiting from his collapse.

$30 Million in Tips

Despite the staggering amounts of money he was losing, Terrance Watanabe was adored by many of the people working the casino floor. Dealers, servers, security — anyone who crossed his path — often walked away with far more than just a good story.

He would periodically hand complete strangers, people he had briefly shared an elevator with, a $25,000 casino chip for no reason at all. On another occasion, when casino staff mentioned they were craving In-N-Out Burger during a late-night shift, Watanabe offered the fast-food chain $50,000 to reopen in the middle of the night so he could buy food for them. They did.

He was known to pay off employees' mortgages, give away $100,000 Tiffany gift cards, and tip in the millions. According to his own estimate, Watanabe gave away at least $30 million in tips and gifts, much of it spontaneously. He wasn't showing off. It wasn't performative. It was compulsive generosity — the kind that made him beloved even as he unraveled.

But while his tips kept flowing, his losses piled up faster.

5.6% of Revenue

Internal memos later revealed that 5.6% of Caesars Entertainment's entire gambling revenue that year came from Watanabe alone. That's one man — single-handedly responsible for propping up a publicly traded casino empire.

And yet… no one told him to stop.

The Losses

By the end of 2007, the numbers were incomprehensible. Court filings and casino records would later reveal that in 2007, Terrance wagered $825 million. When it was all said and done, he LOST $24 million that year, a figure so large that even his own legal team underestimated it at first.

But that's not even his total loss number. The total amount Watanabe lost during his time in Las Vegas? Over $350 million.

No one in modern casino history — in Vegas or elsewhere — has ever lost as much personally through gambling.

The Fall

Watanabe was drinking constantly. He was using painkillers and cocaine. And in the middle of this descent, casinos kept raising his betting limits, allowing him to wager up to $400,000 on a single hand. When he fell, he fell hard — and casinos made sure there was always a table ready for him to fall at.

Eventually, even he knew something had broken. In late 2007, over Thanksgiving dinner, Watanabe admitted the truth to his sister. She had flown in to visit him in Las Vegas and had no idea how bad things had become. Two weeks later, she returned and packed up his belongings. He left Vegas for good.

In his recent interview, Watanabe shared something he had not said publicly before: he was diagnosed as bipolar. The compulsive behavior. The grand gestures. The inability to stop. He believes now that his mental illness went undiagnosed for years — and was exacerbated by addiction, isolation, and unlimited access to everything.

Since leaving Las Vegas, he has attended rehab twelve times, including an 18-month stay at the Betty Ford Center. He has lost nearly all contact with his wealthy siblings, and says he has never asked them for money — out of pride.

Today, Terrance Watanabe lives on Social Security.

Epilogue: The Lawsuit, the Settlement, the Legacy

In the wake of his losses, Terrance Watanabe didn't quietly disappear. In 2009, he filed a civil lawsuit against Harrah's Entertainment, alleging that the casino had knowingly enabled his addictions — plying him with alcohol and drugs in order to keep him gambling. Harrah's responded with a lawsuit of their own, accusing him of failing to repay $14.7 million in credit markers.

The Clark County District Attorney took the extraordinary step of filing four felony charges against Watanabe — an unprecedented move in what had historically been considered civil territory. But the case never went to trial. In 2010, all criminal charges were dismissed, and the two parties reached a confidential settlement through arbitration. The exact terms were never made public.

In the end, Watanabe repaid $112 million of his debt before the lawsuit was filed — and walked away from the case legally cleared, financially ruined, and publicly humiliated.

For Las Vegas, the fallout was quieter. Casinos never formally admitted wrongdoing. But Watanabe's story — and the headlines that followed — prompted increased scrutiny around how high-rolling gamblers are treated, particularly those who exhibit signs of addiction or mental illness. His case was a catalyst for early conversations around responsible gaming, even as the industry quietly moved on.

Today, Watanabe's name is rarely spoken aloud on the Strip. His records remain untouched. No individual has lost more money in a casino than he did — a title he never wanted, and one that will likely never be surpassed.

His story has been optioned for a feature film, a documentary, and a book. He says he's telling it now in hopes that it helps someone else — someone chasing losses, or chasing escape, or just chasing something they can't quite name.

"I thought I could get it back," Watanabe says in the interview. "Even after everything — I thought I could win it back." He never did 🙁

Here is WagerTalkTV's exclusive first-ever interview with the man himself, Terrance Watanabe: