In his 2006 biography, professional golfer John Daly revealed that he gambled away $55 million during his lifetime, up to that point.

Some yet-to-be-named NFL player lost $8 million gambling on games last season.

These are staggering numbers. But in the sports media world there has always been a low-key understanding that professional golfer Phil Mickelson's gambling habits put everyone to shame. No one has ever understood the full extent or the 100% accurate history of Phil's sports betting. But some very interesting allegations have slowly dripped out over the years.

For example, a year ago a sports writer named Alan Shipnuck released an excerpt from his book, "Phil: The Rip-Roaring (and Unauthorized!) Biography of Golf's Most Colorful Superstar," which claimed that Phil lost $40 million gambling in a four year period between 2010 and 2014.

Today a new allegation about Mickelson's gambling dropped. Once again it comes from a book excerpt. But this book is written by arguably the most credible Mickelson gambling source on the planet. Someone who had a front row seat to Phil Mickelson's betting history for nearly a decade. Someone who went to jail and lost tens of millions of dollars directly because of Phil Mickelson and his gambling.

(Photo by Patrick Smith/Getty Images)

Billy Walters

Billy Walters is commonly referred to as the most successful sports bettor in the world, perhaps of all time. Over a 30-year period, Billy generated hundreds of millions of dollars betting on sports. By his own admission, at his peak he was making "between $50 million and $60 million on a good year."

Billy used those winnings, and his general business acumen, to build a net worth that has been estimated at as low as $200 million and as high as $500 million. He owns several golf courses, multiple car dealerships and car rental agencies.

Unfortunately Billy found himself in a bit of trouble a few years ago, and it had nothing to do with gambling. In April 2017 he was found guilty of insider trading. He allegedly made over $40 million using inside information on the stock of a company called Dean Foods. He was sentenced to 5 years in prison and ordered to pay a $10 million fine. He entered prison in February 2017 and was released in the middle of 2020, two years early thanks to COVID and overcrowding.

In his soon-to-be-released book, "Gambler: Secrets from a Life at Risk," Billy places the blame on his legal troubles and subsequent prison term squarely on one man: Phil Mickelson. His former best friend. Phil had to repay $1 million he reportedly earned using inside info passed by Billy.

"Frankly, given Phil's annual income and net worth at the time, I had no problems with his betting. And still don't. He's a big-time gambler, and big-time gamblers make big bets. It's his money to spend how he wants."

"I never told him I had inside information about stocks and he knows it. All Phil had to do was publicly say it. He refused. The outcome cost me my freedom, tens of millions of dollars and a heartbreak I still struggle with daily. While I was in prison, my daughter committed suicide – I still believe I could have saved her if I'd been on the outside."

Getty Images

Aside from placing blame, Billy has used the pages of his book to shed some much-needed light on Phil Mickelson's betting history, once and for all.

Here's the big revelation:

According to Billy Walters, over a 30 year span, Phil Mickelson has made over $1 billion worth of sports wagers and has lost $100 MILLION.

According to Billy, Phil attempted to bet $400,000 on the 2012 U.S. Ryder Cup, a tournament in which he was participating.

Citing two reliable sources, Billy claims that Phil made the following wagers between 2010 and 2014 alone:

• Betting $110,000 to win $100,000 on 1,115 occasions, and betting $220,000 to win $200,000 on 858 occasions. That's $311 million worth of bets.
• In 2011, Mickelson placed 3,154 bets for the year, and on a single day (June 22) he placed 43 bets on Major League Baseball games that resulted in $143,500 in losses.
• He placed 7,065 bets on football, basketball and baseball."

"Based on our relationship and what I've since learned from others, Phil's gambling losses approached not $40 million as has been previously reported, but much closer to $100 million. In all, he wagered a total of more than $1 billion during the past three decades."

Read more: Phil Mickelson's (Alleged) Lifetime Gambling Losses And Total Dollars Wagered Are… Difficult To Accept

As you might correctly guess, John and David are both multi-billionaires. They are the only owners of Two Sigma, and they have equal voting power over all company decisions.

There's just one problem: They hate each other.

Actually two problems.

Not only do they hate each other and can no longer communicate over basic firm functions, John Overdeck is now going through a divorce, which has thrown another wrench into their already very messy lives.

David Siegel, Michael Bloomberg, and John Overdeck (Photo by Craig Barritt/Getty Images for Bloomberg)

How do you split a $60 billion hedge fund?

John Overdeck is a math genius. Math is in his blood. His father was a senior mathematician for the NSA. His mother was a director at Computer Sciences Corporation, a pioneer in the IT field. In 1986, when he was 17, John won a silver medal at the International Math Olympiad. He earned a degree in math and statistics at Stanford before enrolling in Stanford's graduate school to earn a Ph.D in… get this… math.

John never got that Ph.D from Stanford. In the 1990s he was recruited away from school to join a recently-launched math-focused hedge fund called D.E. Shaw. At D.E. Shaw, John quickly rose to the position of managing director of risk management.

More importantly, while he was at D.E. Shaw John caught the attention of the firm's youngest Senior Vice President, a 30-year-old fellow math nerd named Jeffrey Preston Bezos.

Jeff had recently married his research assistant, the future MacKenzie Scott, and in 1994 Mr. and Mrs. Bezos quit the hedge fund and drove across country in a Volvo to Seattle, where he planned to launch an e-commerce business. Jeff wrote the business plan while MacKenzie drove. The business was originally called "Cadabra." Cadabra soon was renamed Amazon.com.

One of the first people Jeff recruited to join him in Seattle was John Overdeck. John's title said Vice President, but he was really a Jeff Bezos's technical assistant.

John worked at Amazon for two crucial years, from roughly 1995 to 1997. I couldn't figure out exactly when he joined or when he left, but considering Amazon went public in May of 1997, it's probably safe to assume that John worked through the IPO, made a small fortune and decided to take a few years off to enjoy his riches.

FYI, on the IPO date, Jeff Bezos ended the day with a net worth of $120 million. A year later he was a billionaire. By late 1999 Bezos was worth $10 billion. After the dotcom bubble exploded in 2001 Bezos' net worth crashed all the way back down to $2 billion.

That same year John and another D.E. Shaw alum named David Siegel, decided to launch a hedge fund. They called it Two Sigma. There was actually a third founder named Mark Picard, but he retired in 2006.

Two Sigma

Right out of the gate Two Sigma raised over $100 million from investors including Jeff Bezos.

In its first decade of operation, Two Sigma returned an average of 30% per year to its investors. This was significantly higher than the average return generated by the average hedge fund in the same time period.

Two Sigma's success was due to its use of cutting-edge technology and its focus on quantitative analysis. The firm employed hundreds of mathematicians, physicists, and computer scientists to develop trading algorithms that could exploit market inefficiencies.

As we stated previously, Two Sigma is the third-largest hedge fund in the world today with $60 billion under management. John and David's former firm, D.E. Shaw, manages around $50 billion.

And, as we stated previously, despite all their success, today John and David hate each other.

Over the years John and David have clashed plenty of times over everything from succession planning, promotions and investment decisions. That's not abnormal. What is abnormal is when the animosity between the owners gets so bad that the fund is forced to make an SEC disclosure that basically says "our founders hate each other, they're unable to make basic decisions together and that might turn into a risk for investors."

John and David haven't appeared at event together in years. The photo above with Michael Bloomberg is from 2017. It's the most-recent photo of them together I could find in Getty. Insiders claim they frequently "snipe" at each other during meetings in front of subordinates.

The friction is making it difficult "to retain or attract employees (including very senior employees) and could continue to impact the ability of employees to fully implement key research, engineering, or corporate business initiatives."

John and David each have equal voting rights (one vote per person). They are apparently stalemating on every single decision, big or small. There's no mechanism for breaking the stalemate. And that's a huge problem considering what is going on in John's personal life.

John and Laura Overdeck via Getty

John's Divorce

In 2002 John married Laura Anne Bilodeau. In 2011 John and Laura established the Overdeck Family Foundation which primarily focuses on STEM education charities and research. Guess what the "M" in "STEM" stands for… MATH.

In 2012 Laura founded a non-profit called Bedtime Math, a free website and app with the goal of making "math a fun part of kids' everyday lives, as beloved as the bedtime story."

Unfortunately that love of math is not helping David, John and Laura figure out how to split Two Sigma.

Their equity stakes in Two Sigma have given both John and David a net worth of $7 billion. John is one of the richest people in New Jersey.

Unfortunately, having a net worth of $7 billion that is largely based on the equity value of a private company doesn't mean you have billions in liquid cash lying around to payout a divorce settlement. And that's where a new conflict has arisen.

After 20 years of marriage, WITH NO PRENUP, John and Laura are divorcing. Common sense would say that Laura is entitled to a payout of $3-3.5 billion. John can't give her that payout without selling part of his stake in Two Sigma. He doesn't want to do this because selling some of his equity would give David majority ownership, and therefore full control. And in another twist, David doesn't even want to be in control. He wants to retire, but he DOESN'T want John to be in charge.

This all adds up to a serious quagmire that won't be easily solved, no matter how much you love math.

Read more: They Co-Own A $60 Billion Hedge Fund. They Hate Each Other. One Is Getting Divorced (With No Prenup). And It's A Huge Mess.

In MrBeast's lawsuit, he accused VDC of creating "low quality" and sometimes "inedible" food that carried his name. Furthermore, MrBeast's lawsuit claimed he had not earned a single dollar over the course of the three year partnership despite millions of burgers being sold.

VDC's suit say that it was MrBeast himself who undermined their shared business endeavors by making disparaging statements and driving away customers.

In a press statement a week ago, VDC called MrBeast's lawsuit "meritless" and "ill-advised". VDC also claimed it was all a ploy for him to get out of their contract.

Now, VDC is taking its response to court, and the lawsuit is nothing if not strongly worded:

"This case is about a social media celebrity who believes his fame means that his word does not matter, that the facts do not matter, and that he can renege and breach his contractual obligations without consequence. He is mistaken."

Dave Kotinsky/Getty Images

"This wanton conduct has caused Plaintiffs to suffer enormous financial harm," the suit states, and now they're seeking a reported $100 million in damages:

"Donaldson's baseless and unlawful disparagement had the intended effect: MrBeast Burger's reputation was materially damaged if not destroyed, customers abandoned the Brand, Plaintiffs' hard-won relationships with vendors, partners, and suppliers were shattered, causing damages to Plaintiffs that, according to the evidence and Donaldson's own statements regarding the value of MrBeast Burger, are in the nine-figure range."

The suit also points to tweets made by MrBeast complaining about the quality of VDC's MrBeast Burger products, and lamenting his "bad deal" in agreeing to license out his name and likeness for the ghost kitchen delivery burgers.

MrBeast is not the only celebrity who has had a VDC partnership. Others include Mariah Carey, Mario Lopez and DJ Pauly D.

Read more: MrBeast Now Facing $100 Million Lawsuit From Ghost Kitchen Company Behind His MrBeast Burger

Dave had already earned a $100 million net worth selling Barstool for around $400 million over several transactions, the last of which closed exactly one year ago. And as if that wasn't impressive enough, yesterday he pulled-off a Jujutsu move that has left media business owners and observers, including myself, absolutely drooling.

Yesterday Dave re-acquired 100% of Barstool for… $1.00. That's not a typo. A buck.

What? Why? How?

(Photo by Tom Briglia/ Getty Images)

The History of Barstool's Sales

Dave Portnoy founded Barstool Sports in 2003 as a print publication for Boston sports. In 2007 Barstool launched a website, expanding the content beyond the Red Sox, Bruins and Patriots to all teams and sports. It added a merchandising business, podcasts, video series, social media… and more.

With its focus on humor and no-holds-barred opinions and commentary, Barstool struck a nerve, mainly with young male sports fans. It found a large audience that up to that point was being totally ignored by the reigning stodgy sports giants like ESPN and Sports Illustrated. Over the next few years, especially with the advent of Instagram and other short-form social media where the company's scrappy talents really shined, Barstool's audience grew and grew and grew.

In January 2016, The Chernin Group acquired a minority stake in Barstool for $15 million. Two years later, Chernin kicked-in another $25 million to up its stake to 60%. With both transactions, Dave remained 100% in charge of Barstool's content. And with no co-founders, he kept 100% of the $40 million (after taxes).

Barstool kept growing. And growing.

In January 2020 a company called Penn Gaming paid $163 million to acquire 36% of Barstool. At this transaction, Chernin's stake was reduced to 36%, while Portnoy owned 28%.

Through some agreements that were baked into the January 2020 transaction, Penn soon exercised the right to increase its stake to 50%. And then in August 2022, an SEC filing showed that Penn exercised its right to buy 100% of Barstool.

Between all transactions, Penn Gaming paid $351 million, all-in, to acquire Barstool.

Over the course of all of the transactions dating back to Chernin, plus Penn Gaming equity he received, Dave Portnoy earned a net worth of at least $100 million.

Re-Acquired For A Buck

Yesterday, Penn Gaming announced it had entered into a $2 billion long-term exclusive betting partnership with ESPN. The partnership will be called "ESPN Bet" and, crucially for this article, the terms of the deal do not allow Penn Gaming to have other betting partnerships. That's a problem because Penn had previously renamed its betting brand "Barstool Sportsbook."

There are other issues.

ESPN is owned by Disney. As you know, Disney maintains a squeaky clean image that is polar opposite of Barstool and Portnoy.

And there's also some bad blood here. Back in 2017, Barstool had a show on ESPN called "Barstool Van Talk." ESPN aired it ONCE, on a Tuesday night at 1am on ESPN2. The abrupt canceling did not please Portnoy, who then very publicly shamed ESPN executives and on-air talent.

To recap.

• It wanted to secure a partnership with ESPN.
• It knew Disney probably wanted nothing to do with Barstool and Portnoy. And vice versa.
• It couldn't continue operating Barstool Sportsbook.

So what was Penn Gaming to do?

An obvious idea would be to sell Barstool to the highest bidder. But who would buy Barstool? A brand that is still entirely driven by the sheer force of personality of Dave Portnoy. Can you imagine Portnoy happily working under some new owner? With a net worth of $100 million, a huge social platform and a history of not exactly being a go-along-to-get-along kind of guy… this was not a real option.

In my opinion, Portnoy and Penn knew Barstool was only valuable to one buyer: Dave Portnoy. And that's what happened.

According to Penn's just-released quarterly report:

"PENN sold 100% of the outstanding shares of Barstool to David Portnoy in exchange for a nominal cash consideration ($1.00 dollar) and certain non-compete and other restrictive covenants."

$1.00.

Why not try to get more than $1? Several reasons.

First, they realized they only had one viable buyer (Dave Portnoy) and having one buyer does not leave the seller with a lot of room to make demands.

Second, selling for $1 allows Penn to maximize a future write-off. In its just-released quarterly report, Penn Gaming revealed that over its time as owner of Barstool, it spent $551 million on the brand. Presumably, that's $351 million to buy the company and another $200 million in various costs and investments in the last three years. Penn will be able to use that $551 million to counter an equivalent amount of profit, perhaps over several years, giving them $551 million in tax-free earnings.

Finally, Portnoy did agree to some key incentives.

In addition to agreeing to never disparage Penn Gaming or ESPN, Barstool can't license the Barstool name to another sports book AND – most importantly – Dave agreed to give Penn Gaming 50% of any money he earns from a future sale of Barstool, seemingly forever.

To recap.

Dave Portnoy started a magazine in 2003. He turned it into a website. He earned a $100 million net worth selling the company for $400 million over several transactions. And then he bought his baby back for a single, solitary dollar.

Please dear God let me find that same deal for CelebrityNetWorth some day.

Read more: A Year Ago Dave Portnoy Sold Barstool For $350 Million. He Just Bought It All Back For… A Dollar.

Per Adidas, the company sent $50 million to a Yeezy bank account in Wyoming, the former home of Ye. Adidas also pushed another $25 million into Yeezy's New York-based JPMorgan Chase account. All of that money was supposed to go to an annual marketing fund that would ultimately deploy a total of $100 million. According to Adidas, the $75 million it sent was immediately moved to another account that helped fund other Yeezy ventures

That's in violation of the agreement of the former partnership, and it could cost Ye a ton of money — unless he can get creative.

Jonathan Leibson/Getty Images for ADIDAS

$200 Million $100 Million

Ye and Adidas began their partnership in 2016. For every shoe Adidas sold, Ye earned a royalty. At his peak, he was earning over $200 million per year in royalties alone. In 2020 and 2021, Yeezy sales accounted for 10% of Adidas' annual gross revenue.

But that's not all.

On top of his shoe royalties, Kanye's deal entitled him to a $100 million annual marketing slush fund that could be used at his discretion. The fund would be paid in quarterly installments of $25 million. The funds were meant to be "restricted to marketing purposes," but what defined a marketing purpose is a bit vague.

For example, in 2019 Kanye told Adidas he spent $50 million of the fund putting on his "Sunday Service" gospel choir tour, and the company didn't seem to blink.

In May of 2023 Adidas sought a court order which would have required Kanye to hand over $75 million worth of funds it claims he misappropriated or simply was no longer able to use for valid marketing purposes. In its May 2023 filing, Adidas claimed there was urgency to have the $75 million returned because it had heard rumors about the rapper's solvency.

Adidas claims it paid $75 million in 2022 in three installments. It also claims that Kanye immediately transferred the funds to a separate account where it was commingled with other funds, violating the terms of their deal.

Adidas is seeking the full $75 million plus unspecified monetary damages, but they'll knock some money off the bill if Yeezy can demonstrate some of the funds were used to legitimately market products through the partnership.

Adding to the legal battle: Ye claims the Yeezy shoe designs are his and that Adidas has copied those designs to sell at lower prices. Adidas alleges it owns all of the shoe designs. Adidas is also being sued by shareholders, who believe the company didn't disclose just how bad the issues were with Ye.

However this legal battle turns out, the split with Ye has been devastating for Adidas. The company still has hundreds of millions of dollars worth of leftover Yeezy shoes and is hoping to sell as much as it can while donating some proceeds to charitable organizations that were also impacted by Ye's words and actions. It turns out that people still want to buy Yeezys — in March, Adidas told investors it was expecting an operational loss of $775.1 million but updated that projection in July to a $498.3 million loss after strong Yeezy sales.

Still, Adidas is on track for its first operational loss in 31 years. Somewhere, we imagine Ye is saying, "Don't act like I never told ya."

Read more: Kanye West And Adidas Are Feuding Over A $100 Million Marketing Slush Fund

With a total of 16 bedrooms and 11 bathrooms spread across the 18,000-square-foot main house that dates back to well over 100 years ago, Aultmore sits on a beautiful 24-acre lot that's surrounded by the dense greenery of Cairngorm National Park. The property listing mentions updates to the home's plumbing and electrical systems between 2007 and 2008, so this is one property that's been brought relatively up to date in addition to its historic charm. The listing goes on:

"The property is approached via a private tree-lined driveway with a turning circle and parking area to the front. The A-listed property has retained many of the features and designs from the original owner with the main elevation having a delightful symmetrical appearance with large astragal windows, and an elegant columned central block flanked by two stone gazebos. The internal features are superb with Adam style marble fireplaces in most reception rooms, beautifully detailed plasterwork on ceilings and archways, superb timber floors and facings throughout."

Why would Bob Dylan want to get rid of such a gem, especially after nearly 20 years of ownership? As realtor Tom Stewart-Moore explained to the Scottish Daily Express, it's because he and his brother just don't get to use it as much as they used to:

"They've not been able to use it in recent years, and that's the reason for the sale. Up until about pre-Covid times, Bob and his brother would normally go there for a few weeks a year."

Amenities in the mansion include a billiard room, drawing rooms, and a formal dining room, in addition to its myriad other historical details. Then there are the equally charming outdoor touches like the property's two gazebos, fountain, walled garden, and pond.

The mansion has been available to rent in the past for weddings and other functions. You can see just such a wedding at Aultmore in the video below from Thistle Production and get an idea of what the property is like:

Read more: Bob Dylan Lists Scottish Estate For $4 Million

Two large cannabis companies, Cresco Labs and Columbia Care, were all set to merge — in a deal worth $2 billion — and form the largest cannabis entity in the United States. But with a shaky economy and worry over regulatory issues, the two sides called the deal off.

As part of the merger, Diddy would have owned nine stores across New York, Massachusetts, and Illinois. Each state would have also had its own production facility. He was ready to pay $185 million for the stores and facilities.

Unfortunately that deal is now up in smoke. And while he didn't lose his $185 million, that was just a planned investment, Diddy is the rare position of feeling shafted by a business opportunity.

Neilson Barnard/Getty Images

Diddy isn't resting on his laurels, though. He and his Combs Global team are still looking at ways they can diversify the cannabis industry.

"My mission has always been to create opportunities for Black entrepreneurs in industries where we've traditionally been denied access," Combs said at the time the deal was announced. "This acquisition provides the immediate scale and impact needed to create a more equitable future in cannabis."

New York, Massachusetts, and Illinois have all legalized marijuana in the past seven years, but there are obstacles standing in the way of the industry's growth. Marijuana is still illegal at a federal level. It's also classified as a Schedule I drug, alongside much more harmful drugs like heroin and LSD.

The Schedule I classification states that these drugs have a high potential to cause addiction or abuse and serve no medical purpose. That classification hampers the availability of marijuana in some cases, and it's largely inaccurate. Cannabis isn't as addictive as many drugs, including tobacco and alcohol. And it's used to ease chronic pain and treat things like glaucoma and cancer.

For now, it's back to the drawing board for Diddy and company. Yet, with his passion for shaking up the industry, we expect to see another deal pop up soon.

Unfortunately this is Diddy's second business snafu in as many months.

Back in May, Diddy sued Diageo, his partner in a tequila brand called De Leon. The lawsuit essentially accused Diageo of being racist and suppressing De Leon while other equivalent tequilas, some of which Diageo also owned, grew into billion dollar brands. A few weeks later, Diageo severed all ties with Diddy, ending what had once been a very fruitful partnership that launched with the vodka brand Ciroc. In its public declaration of the partnership being ended, Diageo claimed Diddy only invested around $1,000 in De Leon and that's why the brand failed. Furthermore Diageo revealed that it had paid Diddy $1 BILLION in royalties over the course of their partnership.

Diddy can't win with tequila or weed. He lost his vodka brand. The guy is not having a great 2023 business-wise!

Read more: Sean "Diddy" Combs Is On The Outside Looking In After A Billion-Dollar Cannabis Merger Fails

For pro athletes, who tend to have at least hundreds of thousands — if not millions — of dollars in disposable income, betting can be an exciting way to pass the time and potentially increase your earnings. And after the Supreme Court allowed states to legalize sports gambling in 2018, more than half of the U.S. states have made it official.

However, there are some rules that athletes must adhere to. They're typically restricted from betting on the sport they play. And they're especially not allowed to bet on their own team.

Yet Denver Broncos defensive end Eyioma Uwazurike is accused of doing just that — and he's facing criminal charges in both Iowa and Colorado.

Eyioma Uwazurike (Grant Halverson/Getty Images)

Uwazurike played at Iowa State through the 2021 season and is one of four current and former Cyclones charged by the Story County Attorney's Office. The players are accused of tampering with records during an investigation into sports gambling from both Iowa and Iowa State athletes. Among the group: Iowa State's quarterback, Hunter Dekkers, who started all 12 games last year. Prosecutors in Johnson County have also charged three athletes with the same crime, including a football player, a former baseball player, and a men's basketball player.

The charges assert Uwazurike made about 32 bets involving events and players, including five games from the 2022 season. One of those games was the team's Week 15 victory against the Arizona Cardinals — a game Uwazurike was on the field for. Prosecutors also say Uwazurike bet on four Iowa State games while in college, including the team's rivalry game with Iowa and a win over Kansas.

Dekkers made plenty of bets, too — "approximately 297," and 26 on Iowa State events, per prosecutors. Dekkers wagered at least $2,800 among the bets, including on a game against Oklahoma State in 2021 when he was the second-string quarterback.

Uwazurike is also looking at criminal charges from the district attorney in Colorado. It's illegal to bet on a sport you play in, per Colorado state law. Dekkers could potentially be banned from the NCAA, too — the organization prohibits players from betting on or against their own school.

In the meantime, the NFL has suspended Uwazurike for at least this upcoming season. The league doesn't allow players to bet on any NFL-related activities, and they're not allowed to place bets if they're at a team facility. It's not the first time the NFL has suspended someone for betting, either.

Uwazurike is hardly a high-profile name. He's a fourth-round draft pick who played in eight games last season. But his actions could uncover a wider ring of player gambling — or, at the very least, it will give the NFL plenty to think about as it embraces betting on its games.

Read more: Denver Broncos Defensive End Eyioma Uwazurike Faces Criminal Charges For Betting On His Own Team

Wesley Snipes worked his butt off for more than a decade to reach the pinnacle of wealth and success in Hollywood. He smashed through perceptions and stereotypes along the way to becoming arguably the biggest action star on the planet in the 1990s. Along the way he earned tens of millions of dollars, mostly from his blockbuster film salaries. Unfortunately, like many other stories of Hollywood ascension, what goes up must come down. But unlike most fallen stars who succumb to drugs or alcohol, Wesley Snipe's personal demon was much more bland.

During that career pinnacle when he was earning tens of millions of dollars, Wesley Snipes wasn't paying his taxes. Amazingly, he truly believed he did not have to pay. He believed so strongly that he fought all the way up to the Supreme Court. This is the story of how Wesley went from Passenger 57 to prisoner #43355-018…

Wesley Snipes Tax Problems / Frazer Harrison/Getty Images

The Rise: Snipes The Action Star

When Wesley was 23, an agent discovered him in 1985 during a martial arts competition. A year later he made his film debut in the 1986 Goldie Hawn movie "Wildcats". That same year, he appeared on the hit TV show "Miami Vice" as a drug-dealing pimp. In 1987, Snipes put his dance performance training and martial arts skills to good use when he appeared in the Martin Scorsese directed music video of Michael Jackson's "Bad". That video caught the attention of director Spike Lee, who offered Snipes a small role in "Do The Right Thing". Snipes turned Lee down, opting for the larger part of Willie Mays Hayes in "Major League".

"Major League" was the first in a string of big box office hits for Snipes throughout the late 1980s and 1990s. He appeared in Spike Lee's "Mo Better Blues" and as the lead in the interracial relationship at the center of the drama in "Jungle Fever". Snipes' role as the drug kingpin Nino Brown in 1991's "New Jack City" was written especially for him and his amazingly nuanced performance cemented his status as a Hollywood superstar. Snipes worked steadily throughout the 1990s in films such as "Passenger 57", "Demolition Man", "Money Train", "The Fan", "U.S. Marshals", "Rising Sun", and "To Wong Foo, Thanks for Everything! Julie Newmar" in which Snipes played a drag queen.

Snipes was on a roll, showing audiences and Hollywood studio executives that he had range- playing everything from drug lords to drag queens. In fact, in 1997, Snipes won the Best Actor award at the Venice Film Festival for his dramatic performance in the Joe Eszterhas written, Mike Figgis directed film "One Night Stand". The film was a flop, in large part due to an interview Snipes gave in Ebony magazine in which he lashed out at African American women and listed all the reasons he didn't date them.

The following year "Blade" gave Snipes his biggest box office success, grossing more than $150 million worldwide. Snipes also was awarded with a star on the Hollywood Walk of Fame and an honorary doctorate from his college alma mater, SUNY/Purchase. Blade was also turned it into a franchise. Wesley was at the top of the Hollywood food chain and the peak of his career. Unfortunately, off set Wesley's arrogance and ego were beginning to lay a path of destruction in his life that would last for more than a decade.

As the third installment of the "Blade" franchise was getting ready to go into production, Wesley's arrogance led him to believe that he was owed input on every aspect of the production. New Line froze him out of all decisions, which pissed Snipes off mightily. Snipes filed lawsuits against New Line Cinema and the director of "Blade: Trinity", David S. Goyer, claiming that he was intentionally cut out of casting decisions and that his role was reduced to make more time for the roles of co-stars Ryan Reynolds and Jessica Biel. The suit with New Line was settled, but Snipes' problems were just beginning.

Unlike most Hollywood celebrities, Wesley's self-imposed path of destruction did not involve a single drug or a drop of alcohol. Wesley's downfall involved something far more dangerous than drugs and alcohol: The Internal Revenue Service.

The Fall: Snipes The IRS Protestor

Wesley's problems with the IRS date back to 2006 when he was charged with attempting to avoid paying taxes and filing $12 million worth of false refunds dating all the way back to 1996.

Between 1996 and 2004, Snipes earned approximately $37.9 million from various acting jobs. Unfortunately, during those years he apparently failed to pay a single penny in taxes.

In 2002 Wesley bought a lavish 10,000 square foot mansion in Alpine, New Jersey. He paid $5.6 million.

Within a few years he also stopped paying the property tax bill. Here's the mansion:

He was forced to sell this home in 2014 at a $2.1 million loss.

As if failing to pay taxes for many years wasn't bad enough, Wesley took things a step further.

Wesley also used forged documents to receive $12 million worth of undeserved refunds reflecting his income between 1996 and 1998. So why did he essentially ignore and steal from the IRS? This is where the story takes a crazy turn. Wesley explained his actions by using a controversial tax theory called the..

"861 argument"

The "861 argument" revolves around the language of section 861 of the Federal tax code. People who use this 861 argument claim the tax code's language makes domestic income of U.S. citizens and residents not taxable. The language instead states that "compensation for services" is taxable. This argument claims that because the 861 provision does not specifically list wages, for example from acting in a movie, they therefore are not taxable. As a side note, the 861 argument has never been successful for anyone in the history of American tax law. Furthermore, Snipes failed to file tax returns for 1999, 2000, 2001, 2002, 2003, and 2004.

Unfortunately, the government wasn't buying what Wesley was selling. Wesley Snipes spent four years battling the government on his tax charges. He went to trial in February 2008. His defense team intimated that their defense would take a month and they planned to call an illustrious list of witnesses including Muhammad Ali, Spike Lee and even Barbra Walters. However in the end, his defense spent just ONE HOUR arguing his case.

The prosecution was not as brief. They presented what was a fairly rock solid and simple case of a person earning $40 million, paying zero in taxes AND requesting $12 million in refunds.

Wesley was found guilty of three misdemeanor counts of failure to file federal income tax returns. He was sentenced to three years in prison. And while three years may sound like a long sentence for a silly tax issue, the prosecution had been seeking a 16 year sentence. So Wesley got off easy in a way.

In addition to his prison sentence, over time Wesley was ordered to pay $17 million in back taxes, interest and penalties to the IRS.

Snipes appealed the verdict without success in 2010. He began his three year sentence at McKean Federal Correctional Institution on December 9, 2010. Snipes took his appeal all the way to the United States Supreme Court, but in 2011 the justices declined to hear the case.

Between December 2010 and April 2013, Wesley Snipes served 845 days in federal prison in McKean County, Pennsylvania. He served 90% of his three year sentence.

Wesley was released from prison on April 2, 2013.

An Offer They Can Refuse

After being released, Wesley made what is called an "Offer In Compromise," (OIC) to the IRS.  Essentially with an OIC, a tax offender offers an amount of money he or she hopes the IRS will accept to settle the debt once and for all, typically for pennies on the dollar. By this time, with interest and penalties, Wesley's debt had ballooned from $17 million to $23.5 million. Wesley offered to clear that debt in exchange for an OIC of $842,061, citing his lack of means to pay the remainder. That's 3.5% of the total amount due.

Perhaps not surprisingly, the government rejected his OIC.

This rejection kicked off another legal appeal. That appeal would drag on until November 1, 2018 when a judge upheld the IRS' rejection of his OIC, claiming that Snipes had failed "to provide bona fide documentation to prove his assets and financial condition."

The IRS countered that based on his assets and income potential, Wesley's "reasonable collection potential" was $17,482,152.

After yet another appeal, the IRS extended an offer to reduce the debt to $9,581,027.

Wesley rejected this offer!!! Instead he re-asserted his original OIC of $842,000.

From the judge's ruling:

"Given the disparity between petitioner's $842,061 OIC and the settlement officer's calculation of $9,581,027 as his RCP, as well as petitioner's inability to credibly document his assets, the settlement officer and her manager had ample justification to reject the offer… Accordingly, we conclude that the settlement officer did not abuse her discretion in determining that acceptance of petitioner's OIC was not in the best interest of the United States."

Wesley has continued to work in the years since his release from prison. His first film role of his post prison career was in the third installment of the Sylvester Stallone "Expendables" franchise. He has appeared in a number of television series over the years, and in 2021 he had a memorable part in Eddie Murphy's "Coming 2 America."

I actually can't determine if Wesley has paid off any of his debt. I could not find a recent filing from the government showing he had either paid or failed to pay down what is presumably the $9.5 million proposed offer. Considering how stubbornly he has fought the debt up to this point, maybe he's still fighting. We may not know the answer until the IRS officially clears him after the debt is satisfied OR if they file another suit due to lack of payment. Either way, what's the lesson of this story? Simple. Pay your damn taxes!

Read more: Wesley Snipes Played Chicken With The IRS… And Lost. Badly. Really Badly. He Literally Went From Passenger 57, To Prisoner #43355-018

However, Brady's ownership might be hitting a snag before it begins.

Raiders owner Mark Davis has expressed his interest in employing Brady within the organization on top of his ownership stake. Yet that goes against a new NFL rule that explicitly states employees or family members of employees cannot have any kind of ownership in the team.

Jon Kopaloff/Getty Images

The likely bet is that Brady will find a way to contribute to the Raiders without being formally employed by the organization. But there is the possibility Davis (or Brady) could balk at the rule, and the deal could fall apart entirely.

This isn't Brady's first foray into a Las Vegas team. He purchased the WNBA's Las Vegas Aces in March 2023. The team won the WNBA Championship and Commissioner's Cup in 2022.

Brady had a long and storied career on the field, primarily with the New England Patriots, before finishing his final few seasons with the Tampa Bay Buccaneers. He retired with seven championships and three MVP awards.

Coincidentally, one of his most infamous moments came against the Raiders, back when they were still with Oakland. With under two minutes to go in the 2001 AFC Divisional round, the Patriots trailed the Raiders 13-10 on a snowy field. Brady was sacked and appeared to fumble the ball, which the Raiders recovered. It looked like the game was about to be over, but then the officials reviewed the play. They determined Brady's arm was coming forward, and the play was an incomplete pass, not a fumble.

The "Tuck Rule" kept the Patriots' season alive. They'd go on to win both the game and that season's Super Bowl. It was the first title for Brady and set off two decades of sustained success. The Raiders, meanwhile, reached the Super Bowl the following year, falling to the Buccaneers. Since then, they've only made the playoffs twice, losing in the Wild Card round both times.

If Brady's ownership stake holds firm and he can bring a little Super Bowl magic to the franchise, fans might finally be able to overlook the Tuck Rule game.

Read more: Tom Brady's Raiders Ownership Quest Might Be Falling Apart