Pablo Escobar got to serve time in his own luxury ‘prison’
Pablo Escobar, the creator and leader of the notorious Medellin Cartel, lived large off the massive profits of his criminal activities in the 80s. He was considered the wealthiest criminal in history. When he finally surrendered to Colombian authorities in 1991, he struck a deal to ensure he could live in his own, private and self-built prison, named La Catedral. Here he was able to continue living a glamorous lifestyle, as he paid for a football pitch, waterfall, helipad and jacuzzi onsite. A year later, Escobar escaped and La Catedral was left deserted. Today, it is occupied by a group of monks.
Leona Helmsley used charity to rehabilitate her image
Leona Helmsley (1920-2007) was a billionaire hotelier with a reputation for explosive outbursts and abuse towards her employees. She was nicknamed the ‘Queen of Mean’ for her cruelty, which included evicting her daughter-in-law soon after the sudden death of her son. She was convicted of tax evasion in 1989 and spent 19 months in prison. Once released, however, Helmsley attempted to rehabilitate her image via philanthropy. After 9/11, she donated $5 million to the families of first responders. She gave $65 million to medical research before her death, funding the new Center for Advanced Digestive Care at New York – Presbyterian Hospital.
Jakob Fugger sent gemstones to the Pope after breaking religious law
It is hard to comprehend how wealthy the German merchant Jakob Fugger was in the 1500s. His fortune was around $400 billion in today’s money – more than that of any current billionaire, and equivalent to 2% of Europe’s GDP in that era. Among his assets was a mining business, which was backed in secret by Cardinal Melchior von Meckau. This deal was illegal because it involved earning interest, a practice forbidden by the Catholic Church for its clergy. When the Cardinal died and the investment became public knowledge, Fugger hastily paid a fortune in jewels to the Pope to make amends. He also had to pledge military funding to Emperor Maximilian I in return for his support.
Andrew Carnegie bought a library for a flooded town
Andrew Carnegie was a pioneer of the American steel industry in the 1800s, and he also became one of the most generous philanthropists in history, giving away the modern-day equivalent of $5.5 billion in his later years. However, back in 1889, he faced backlash after a massive environmental disaster. Carnegie was a member of the South Fork Fishing and Hunting Club, which owned an old leaky dam near Johnstown, Pennsylvania. When the dam gave way on May 31, 1889, it killed 2,208 people in Johnstown. The club was never sued, but Carnegie helped to build a new library in the town amid public outcry.
Donald Sterling paid a $2.7 million fine for racist rental practices
Donald Sterling is a billionaire real estate businessman who once owned the San Diego / Los Angeles Clippers. In 2014, he landed a lifetime NBA ban and was forced into selling the team after he made racist comments in leaked recordings of a private conversation. He was also fined $2.5 million. However, a lesser-publicised incident in 2009 saw him pay an even greater settlement fine of $2.7 million, after he was accused of discriminatory housing policies. In particular, he was accused of refusing to rent Beverly Hills homes to African Americans.
Tsar Nicholas II compensated families after a coronation crush
Tsar Nicholas II, whose lavish spending amid dire poverty in Russia contributed to the revolution against the monarchy, faced his first reputational crisis early in his leadership, The 26-year-old became Tsar in 1896, and during his coronation, celebrations took place across his vast nation. In Khodynka Field in Moscow, a massive crowd gathered at the promise of food and gift distribution, leading to a crush that left 1,282 people dead and many more injured. Nicholas’ government hastily paid out compensation to grieving families, although Nicholas was criticised for attending a festive ball on the night of the tragedy, with no show of emotion.
William the Conqueror’s funeral involved an emergency pay-off
William the Conqueror amassed spectacular wealth as the first Norman king of England. In his will, he left generous gifts to the Church and donated money to be distributed among the poor. However, little did he know that his own funeral would require an emergency reparation payment to avoid conflict. At his request, he was buried at Abbaye-aux-Hommes in France, which he had founded. But his funeral was interrupted by claims that the holy site was built on stolen land. This proved to be true, and William’s heirs hastily used part of his fortune to compensate the family whose land was stolen.
Curt Johnson paid a $6,000 fine after assaulting his stepdaughter
S. Curtis “Curt” Johnson is among the wealthiest men in the United States, but he emerged from one court case after paying a fine that was considered astonishingly low. In 2011, he was charged with abusing his teenage stepdaughter over a three-year period, and he pleaded guilty to two misdemeanours in 2014. He was sentenced to four months in jail, with work release privileges after 60 days, and he paid a fine of $6,000. He was not required to register as a sex offender upon his release.
The Ford family sold off their disgraced jungle town project
The billionaire industrialist Henry Ford was lauded for his success with the Ford Motor Company. Less successful, however, was his Fordlandia project, in which he established a prefabricated town in the Amazon Rainforest to house his employees in the rubber industry. Women, alcohol and soccer were all banned in the town, and the employees struggled with the harsh environmental conditions. The project was a disaster and was abandoned after just six years. Two years before Ford’s death, his grandson, aiming to cut the family’s association with the unfortunate region, sold Fordlandia and another town back to the Brazilian government, making a loss of $301 million in today’s money.
Jacqueline Mars paid a $2,500 fine after a fatal car crash
Heiress to the Mars candy fortune, Jacqueline Mars was born in 1939 and is the 22nd richest person in the world. She worked for the family business and retired in 2001. In 2013, at the age of 73, she was driving her Porsche along US Route 50 in Northern Virginia when she allegedly fell asleep at the wheel, crashing into a minivan. One person died in the crash and a pregnant passenger miscarried. She pleaded guilty to reckless driving and did not face a jail sentence. Instead, her driving license was suspended for six months, and she paid a $2,500 fine.
Marc Rich dodged tax evasion sentences by making party donations
The aptly named Marc Rich married an heiress before making huge oil profits from Iraq, Iran and other dodgy regimes. Then he evaded paying tax, fleeing the USA for Switzerland in 1983 and leading the life of Riley, free from conviction. It is believed that his large campaign donations to the Democratic Party may have resulted in a pardon granted by the President in 2001.
Robert Vesco avoided jail by donating money to the future President
Robert Vesco was charged in 1972 for misappropriating over $224 million. His sentence? None. Vesco jumped bail to the Bahamas and eluded capture via extradition law and disguises. It later emerged that Vesco had donated $200,000 to the Nixon campaign and made pals with the president’s nephew. Many claimed this was to dampen the fire of the federal investigation.
Mark Zuckerberg paid huge amounts to settle copyright allegations
You’ve all seen the movie. Or at the very least, you’ve all heard the story. Mark Zuckerberg pinched the idea of Facebook from the Winklevoss twins while studying at Harvard University. But you probably haven’t seen the official figure that brought the brouhaha to an end. In 2009, Facebook Inc. allegedly paid out $65 million to settle a lawsuit filed against it and Zuckerberg.
Lance Armstrong allegedly paid a fellow cyclist to throw a race
Lance Armstrong has gotten himself into a lot of bother over the years. In 1993, he allegedly paid cyclist Robert Gaggioli $100,000 to throw a race. The prize money was a whopping $1 million, and Armstrong had his eyes set on it. He allegedly brought the prize money to Roberto in a cake box after “winning” the race and going on to bigger heights.
Rene Angelil shut down fondling accusations with $2 million
Rene Angelil, who was married to Celine Dion between 1994 and 2016, allegedly paid a California woman $2 million in 2000 to quieten accusations of abuse making the news and damaging Dion’s career. Court records indicated that Angelil agreed to pay Yun Kyeong Kwon after she claimed he touched her inappropriately in an elevator in a Las Vegas hotel.
Brett Favre made a donation after a money misuse scandal
Brett Favre made a donation of over $130,000 to the University of Southern Mississippi Athletic Foundation after he was caught in a money scandal. The former NFL quarterback allegedly paired up with ex-Mississippi Governor Phil Bryant and used welfare funds meant for poor residents to build a new volleyball stadium at the university where his daughter played.
Peter Cook covered up a harassment case with $300,000
Peter Cook, the estranged husband of Christie Brinkley, agreed to pay his former teenage mistress $300,000 to not make a peep about their tryst. The architect also paid Diani Bianchi so that she wouldn’t take him to court for sexual harassment. The two began their affair when Bianchi was just 18 and had gotten a job in Cook’s office.
Louie Anderson paid hundreds and thousands in a blackmail scheme
Comedian Louie Anderson was blackmailed by a man named Richard Gordon in 1997, who threatened to tell the media that Anderson had propositioned him for sex in a casino in 1993. Anderson eventually paid $100,000 in hush money, worried that the story would threaten his promising TV career. When Gordon bumped the pay to $250,000, Anderson’s lawyers informed the feds and got the blackmailer jailed.
Bill O’Reilly paid $32 million to shield his kids from a damaging story
In 2017, Fox News host Bill O’Reilly paid an astonishing $32 million to a woman to who had accused him of harassment and being involved in something described as a “nonconsensual sexual relationship.” O’Reilly, however, even having paid the sum, claims he did nothing wrong, and only did it to shelter his children from the story.
Tiger Woods paid his mistress seven figures
One of Tiger Woods’ many mistresses, Rachel Uchitel, was reportedly paid a staggering $10 million to keep schtum about their affair. When Uchitel decided to break her contract and speak out about the fling, she had to return the money Woods gave her. Uchitel’s lawyer Gloria Allred struck a deal with Woods’ attorney so that a damage suit would not be filed.
Warren Harding bought his mistress a house to raise their secret child in
President Warren Harding made headlines in 1927 when his mistress Nan Britton revealed he had fathered her child out of wedlock. Britton revealed that Harding paid for her to live in a New Jersey house where she secretly gave birth to their daughter Elizabeth in October 1919. She claimed the child had been conceived on a couch in Harding’s Senate office.
Vince McMahon silenced four women with huge payments
Former WWE chairman Vince McMahon was revealed to have paid over $12 million to four women who made “allegations of sexual misconduct and infidelity,” in a Wall Street Journal exclusive. The women were said to have signed agreements with the disgraced McMahon that “prohibit them from discussing potential legal claims against or their relationships with the 76-year-old executive.”
Bill Cosby paid an undisclosed sum to protect his reputation
Bill Cosby was accused of drugging and assaulting a young woman in 2004 at his Pennslyvania mansion. Even though Bill’s lawyers claimed the pills had only been Benadryl, the civil lawsuit was eventually settled with an undisclosed sum of money. But if the rumours were right, it’s easy to imagine this figure being close to seven figures.
Thomas Jefferson paid a journalist to smear political rivals
America’s third president Thomas Jefferson wrote in an 1801 letter about his part in an alleged hush money scheme to his friend, James Monroe. Jefferson revealed he had given money “from time to time” to journalist James Thomson Callender, who later told people that the payments were for writing articles defaming John Adams and George Washington, as well as exposing an affair involving Alexander Hamilton.
Yuan Hongwei paid bail to avoid arrest
Yuan Hongwei was accused of creating and selling counterfeit products and trademarks, including the name ARBO Industries from an Indian company. He was arrested at Heathrow Airport in London in 2008 but after posting a $200,000 bail and surrendering two passports, he escaped to China. He is thought of as a rogue hero in his native home.
Sean Kingston reportedly silenced an accuser with cash
Many people wondered what became of Sean Kingston after his 2007 breakthrough hit Beautiful Girls. Answer: in 2010 when he was accused of assaulting a 22-year-old woman. Kingston later said he decided to offer the victim a cash settlement because he didn’t have time to stand trial thanks to an upcoming album release and tour. The move saw several venues cancel Kingston’s shows.
Eddie Murphy made monthly payments to his ex to look after their daughter
Eddie Murphy was accused of fathering and failing to acknowledge a daughter he had with Mel B in 2007. After taking paternity tests confirmed this, Murphy and Mel B then took the matter to court for 15 months before reaching a settlement in which the legendary comic would have to pay his Spice Girl ex $50,000 a month until their daughter turns 18.
Kanye West paid a quarter of a million after assaulting a teenager
Kanye West was alleged to have assaulted an 18-year-old in Beverly Hills, after the young man used a host of racial slurs about West. It was reported that the rapper settled the case with the teenager for the sum of $250,000, resulting in the teenager dropping all his charges. The police ultimately decided against charging West with battery.
Michael Jackson put abuse allegations to bed with a huge settlement
When 13-year-old Jordie Chandler was sedated during a routine dental check-up performed by his dentist father, he began to profess extremely graphic encounters between him and Michael Jackson. Following a scandalous court trial, the Chandler family were given between $15–25 million in a settlement made by the King of Pop himself.
Roman Polanski fled the country to avoid jail
Famous director Roman Polanski became infamous after he was accused of drugging a 13-year-old girl in 1977. Just prior to his sentencing, Polanski fled America to Europe where he stayed for 15 years. In 1988, the victim sued him for sexual assault, intentional infliction of emotional distress, and seduction. Court documents revealed that Polanski settled the case out of court with a $500,000 settlement.
Mike Tyson paid off ex-wife who accused him of abuse
Robin Givens was always open about how temperamental Mike Tyson could be when they were married in the late 1980s. In an interview the couple gave to Barbara Walters, Givens said the boxing champion “gets out of control, he shakes, he pushes, he swings.” After she accused him of abuse, Tyson paid Givens $10 million.
David Boreanaz silenced his co-star with money
David Boreanaz was accused of assaulting Kristina Hagan on the set of their TV series Bones. He had apparently been sending her lewd text messages, saying he could “make things happen for her”. Hagan’s lawyer, Gloria Allred, who had been involved in many celebrity civil suits, sued FOX and David, who saved his bacon by paying Hagan an undisclosed sum of money.
Cristiano Ronaldo settled a rape charge out of court
Kathryn Mayorga accused footballer Cristiano Ronaldo of sexually assaulting her after they met on a night out in Las Vegas in 2009. Ronaldo denied all the allegations, though his lawyers alleged the two had consensual sex and claimed Mayorga was trying to extort the Portuguese international. Still, they admitted to paying her €375,000 to settle the allegations in 2010.
John Edwards reportedly coughed up $1 million to mistress
Donald Trump wasn’t the first American politician to be involved in an alleged hush money scandal. Senator John Edwards was hoping to become the Democratic presidential nominee back in 2008 when news broke that he had reportedly paid off Rielle Hunter, his mistress, to the tune of $1 million.
Bette Davis prevented affair leaking by paying her husband
1950s Hollywood may appear to be the height of glitz and glamour but there were all kinds of debauchery and underhand dealings going on. Bette Davis’ scorned husband is said to have recorded her in bed with billionaire Howard Hughes. Davis, desperate for the story or recording not to leak, paid her husband $75,000 to keep his lips sealed.
Charlie Sheen kept HIV diagnosis secret with $10 million
Charlie Sheen shocked the world in November 2015 when he revealed he was HIV-positive. Perhaps more shocking was that he’d been living with the disease since 2011, around the time of his public meltdown. It was eventually revealed that the actor had paid several people hefty sums to ensure secrecy about his diagnosis, including $10 million to one adult film performer.
Mario Batali saved his brand with huge payouts
Celebrity chef Mario Batali was facing a huge lawsuit back in 2010, after 1,100 employees claimed Batali had defrauded them out of 5% of their wine and alcoholic beverage sales, taking a “tip credit” from the tip pool to boost profits, and failing to provide over-hours pay. The Iron Chef America judge agreed to settle the lawsuit for a hefty $5.25 million.
American business magnate Larry Ellison loves many things. Mostly planes, yachts and mansions. He does not, however, love sticking to his billion-dollar budget. Emails in 2006 revealed that the Oracle founder frequently maxed out his $1 billion credit limit to finance his expensive toys, much to the annoyance of his accountant, Philip Simon.
The influence of India’s Ambani family has always been clear thanks to their mammoth success with Reliance Industries. Still, it wasn’t until they banned the release of a 1998 book called The Polyester Prince, charting Dhirubai’s rags-to-riches story, that the full extent of their power was fully realised. The book remains banned to this day.
Founder of clothing giant Zara, Spanish businessman Amancio Ortega came under fire by political parties and associations when he masked tax avoidance claims with a $361 million donation to cutting-edge cancer treatment in Spanish hospitals. Many saw this as a way of Ortega absolving himself of a crime.
In 2022, Dell Technologies Inc announced it had reached a $1 billion settlement of a lawsuit accusing it of short-changing shareholders in a dodgy $23.9 billion transaction in 2018 after it became a public company again. The company’s founder and CEO Michael Dell faced widespread criticism for this shadiness.
At one time France’s richest woman, L’Oreal heiress Lilian Bettencourt settled a legal dispute with her daughter in 2010 which prompted investigations into tax and political funding. Bettencourt said the row had begun with a disagreement over her expensive gifts to a family friend, collectively worth €1billion (roughly $1.07 billion US).
David Koch of multinational conglomerate corporation Koch Industries was ordered to pay a staggering $296 million wrongful death award after a leaking company pipeline burned two teenagers to death in 1996. A trial expert witness told a jury “he’d never seen a company disregard safety to this extent in his more than 25-year career.” Koch eventually settled the matter out of court.
Like many of his ilk, Mexican business magnate Carlos Slim has been accused of stifling market competition. One of the most famous examples was his acquisition of Telmex. Slim also bought one of Mexico’s largest makers of copper wire, before forcing Telmex to restrict its copper wire purchases to his own company, ultimately driving a big rival out of business.
When the world was in turmoil over the COVID-19 pandemic, Google co-founder Larry Page simply bought a New Zealand residency (where life was back to normal). The move was widely criticised, with many in New Zealand and abroad questioning why the internet billionaire’s application to live there was approved so quickly, when many skilled workers and fractured families were being rejected.
French business magnate Bernard Arnault allegedly threatened to strip all of his advertising from French newspaper Le Monde after a report published in the paper revealed information about the billionaire’s use of tax havens in the controversial Paradise Papers. This was widely damned as a dismaying insight into how the 1% can control their own press with a firm hand.
Italian businessman Giovanni Ferrero, executive chairman of confectionary company Ferrero SpA, was sued by a Californian mother in 2011 for misleading advertising, as it claimed its flagship product was “healthy” and an example of a “tasty yet balanced breakfast.” The next year, Ferrerio agreed to pay the woman $3 million to settle the lawsuit.
Billionaire Sheldon Adelson was the founder of the Las Vegas Sands corporation, whose properties includ Singapore casino the Marina Bay Sands. In 2020, he paid a settlement of $6.5 million to a Chinese gambler who claimed that the price had been taken from his bank account and transferred to other guests without his approval.
Adriana Ferreyr, the ex-girlfriend of George Soros, took out a $50 million lawsuit against the Hungarian-American billionaire in 2011, which included “claims of emotional torture, harassment and violence - all denied by the twice-divorced Soros.” Mauricio Carneiro, Ferreyr’s lawyer (as well as her cousin), has claimed that Soros offered him $250,000 to drop the suit.
Jorge Paulo Lemann
Brazilian bigwig Jorge Paulo Lemann agreed to pay $10.6 million to settle a five-year-old case where he and two others were accused of abusing their power as controlling shareholders of beverage company AmBev. It was among the highest settlements ever paid by individuals in a financial lawsuit in Brazil.
Australian billionaire mining mogul Gina Rinehart wasn’t too happy with her portrayal in the 2015 mini-series House of Hancock so she decided to put her money where her mouth is, taking legal action and accuser the TV production of being defamatory. A settlement was eventually made with Channel Nine and production company Cordell Jigsaw Zapruder.
In May 2020, Kendall agreed to pay a $90,000 settlement for her involvement in promoting Fyre Festival on social media. The model was among several celebrities who were paid $275,000 to post about the fraudulent event on Instagram, hoodwinking attendees into thinking they’d be partying with A-listers.
Two-time Super Bowl winner Ben Roethlisberger was accused of sexual assault by a Lake Tahoe hotel employee in 2009. Instead of taking the issue up with court, the quarterback decided to pay the victim between $600,000 and $700,000 in a hush money settlement. Roethlisberger was later suspended four games.
When basketball player Kobe Bryant was accused in 2003 of sexual assaulting a 19-year-old ski resort instructor, he denied any wrongdoing, admitting to commuting adultery but claiming the sex was consensual. Nonetheless, the LA Lakers star still decided to settle the matter out of court for an undisclosed sum following several hearings.
The life of pro-football player Donte Stallworth changed forever when he hit and killed a pedestrian with his Bentley after leaving a party in Miami back in 2010. Luckily for him, the police determined the NFL wide receiver was under the influence while driving. Stallworth paid the victim’s family off and served just 30 days in jail.
After five years of legal wrangling, Tatiana Akhmedova, who had hired some of “Britain’s most sought-after lawyers” and was backed by litigation funder, Burford Capital, reached a settlement agreement with her Russian billionaire ex-husband Farkhad Akhmedov, to the tune of £453 million. That’s spare change to him.
Britney Spears was once accused of sexual harassment by her former bodyguard Fernando Flores, who claimed that the singer would make unsolicited forthcoming on him. Spears denied the charge but agreed to pay him an undisclosed sum to keep the news out of the public as fast as possible.
CEO of ArcelorMittal, Lakshmi Mittal was sued by his former friend Moni Varma over allegations that Mittal reneged on an agreement to pay fees on a huge deal he brokered for him in Nigeria. Mittal eventually managed to settle the dispute out of court, somewhere in the millions.
After being acquitted in a 2008 trial, singer-songwriter and serial sex offender R. Kelly paid off a sexual assault accuser to the sum of $250,000. Two years later, he paid off a former housekeeper $100,000 in relation to another assault. Happily, he didn’t get away with it forever, being jailed in 2022 for a minimum of 31 years on racketeering and sex trafficking charges.
Alec Baldwin’s reputation was altered forever in 2021 following the shocking and tragic shooting incident on the set of Rust, which saw the accidental death of cinematographer Halyna Hutchins. The bereaved family later filed a wrongful death lawsuit against Baldwin, who paid up an undisclosed settlement.
The Astroworld tragedy, which saw the deaths of 10 people, rocked the music world in 2021. In the wake, multiple lawsuits were filed on behalf of those injured or killed at the Houston festival. Rapper Travis Scott, founded the event and was performing, later reached a settlement with the victim’s families.
Actress and businesswoman Gwyneth Paltrow got in hot water in 2018, when the FDMD sued her wellness company Goop for selling a vaginal egg that was not “supported by competent and reliable science.” The lawsuit was settled with a payment of $145,000 and a promise to refund any customers who had bought the product.
Rapper Nicki Minaj was sued by singer-songwriter Tracy Chapman in 2018, over the unauthorised sampling of Chapman’s song Baby Can I Hold You? on Minaj’s song Sorry. After Chapman refused to budge, Minaj decided to settle for $450,000 as this would likely have proved less expensive than taking the matter to court.
Actor and filmmaker James Franco paid a $2.2 million settlement following allegations he had pressured female students to take part in explicit sex scenes on camera. The actor had been sued by the former students of his acting and film school in Los Angeles back in October 2019. While no criminal charges were taken against him, the ensuing scandal has largely destroyed Franco’s career.
Russian billionaire Dmitry Rybolovlev’s bank account came crashing down somewhat when his wife Elena filed for divorce after 23 years of marriage. Dmitry, who had been accused of being unfaithful to his wife on several occasions, ended up paying Elena a whopping $4.5 billion on court orders.
Hip-hop presenter Dee Barnes was savagely assaulted by Dr. Dre at an industry party back in 1990. The rapper, music producer and business mogul, who has since condemned the assault and his violent past, settled the issue out of court after being slapped with a $22 million lawsuit by Barnes.
Pharell Williams was sued over his 2013 song Blurred Lines with Robin Thicke after Marvin Gaye’s family claimed it had been lifted from Gaye’s 1977 song Got to Give It Up. In 2015, the family won the case. Pharrell eventually paid $5 million to the estate.