How a $14 Million Lottery Ticket Linked Leonardo DiCaprio, Osama Bin Laden, and a Notorious Crime Boss

Remember those childhood moments when the older kid on the block would snatch your snacks or toys? Well, today’s story is just like that—except it involves $14 MILLION!!

James Joseph "Whitey" Bulger Jr. wasn’t your average neighborhood bully. Born in 1929 into an ordinary Irish-American family, James had an unremarkable childhood. But while his younger brothers excelled academically, James was always more interested in the streets.

At 17, he was arrested for the first time, marking the start of a life of crime. Nicknamed “Whitey” for his blonde hair, he preferred being called “Jimmy” or even “Boots,” a nod to the knife he always hid in his cowboy boots. He became part of Boston’s notorious "Shamrocks" gang, getting arrested for assault, forgery, and armed robbery, and spent time in a juvenile correctional facility.

After being released, Bulger joined the U.S. Air Force, earning his high school diploma and training as a mechanic. However, his criminal ways continued, landing him in military prison for assault. After serving time, Bulger returned to Boston, launching into an era of bank robberies and truck hijackings that earned him a spot in Atlanta’s federal penitentiary. While incarcerated, he claimed to be a victim of the CIA’s MK-ULTRA mind-control experiments involving LSD. Later, he was transferred to Alcatraz, where he focused on education, taking courses in typing and business law.

After serving nine years, Bulger was paroled, but his time as a law-abiding citizen was short-lived.

From Crime Boss to Lottery Thief

By the '70s and '80s, Bulger had solidified his role as the leader of Boston’s Irish Mafia. His empire grew, fueled by extortion, drug trafficking, and violence. Despite his rising notoriety, Bulger managed to evade the law for years, aided by his role as an FBI informant.

Bulger’s connections didn’t stop at local crime; he had ties to the Irish Republican Army (IRA), supplying arms and financial support for their fight against British presence in Northern Ireland.

But here’s where things take a bizarre twist. In 1991, Bulger discovered that a low-level criminal named Joseph "Joe" Murray was holding a winning lottery ticket worth $14.3 million. Murray, who was associated with Bulger’s crew, had bought the ticket with Bulger’s money at a store Bulger owned. Instead of letting Murray cash in, Bulger and his gang decided to take matters into their own hands. They kidnapped Murray, forced him to hand over the ticket, and later killed him—his body was never found.

Bulger and his associates tried to claim the lottery winnings, but lottery officials became suspicious when the ownership of the ticket suddenly changed. This triggered an investigation that revealed Bulger’s involvement in the scam.

The Downfall of Whitey Bulger

From that moment, Bulger’s empire began to crumble. The DEA and Boston police prepared charges of drug trafficking and extortion. It was as if the "lottery curse" had fallen upon him. Bulger fled and remained on the run for 16 years, eventually becoming the second most-wanted man on the FBI’s list—right behind Osama bin Laden. The FBI even offered a $2 million reward for information leading to his capture.

In a twist of fate, the tip that led to his arrest came from his neighbor, Anna Björnsdóttir, a former model, actress, and Miss Iceland 1974. At the time of his capture, Bulger was 81 years old and spent his remaining years in prison until he was found murdered in his cell at age 89.

From Real Life to Hollywood

Whitey Bulger’s infamous life left a lasting mark on popular culture, inspiring numerous books, documentaries, and movies. The most famous of these is The Departed, which featured an all-star cast, including Leonardo DiCaprio, Matt Damon, Jack Nicholson, and Martin Sheen. The film went on to win four Academy Awards in 2007, including Best Director for Martin Scorsese and Best Picture.

Bulger’s story remains a chilling reminder of the dark side of fortune—and the shocking twists life can take when crime and wealth collide.