The Most High Profile Arrests in FBI History

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The Federal Bureau of Investigation (FBI) initially began as the Bureau of Investigation in 1908 and gradually evolved into the United States’ primary federal law enforcement agency. Tasked with fighting crimes ranging from homicide to bank robbery to kidnapping, the FBI is credited with hunting down some of the most legendary lawbreakers in modern history — several during the 48 year tenure of the equally famous (and scandalous) FBI Director, J. Edgar Hoover.

That said, here’s an arresting glance at some of the biggest headline-grabbing bureau busts of all time. 

10. John DeLorean

Most movie fans are familiar with the iconic time travel machine used in the beloved Back to the Future trilogy. But lesser known is the man behind the infamous vehicle, who became snared in an elaborate FBI sting that involved cocaine trafficking. 

John DeLorean was a maverick. As a top executive for General Motors, he helped usher in the muscle car era with popular models such as the Pontiac GTO, Grand Prix, and Firebird. In 1975, DeLorean’s jet-setting lifestyle saw him take flight with the start of his own company, DeLorean Motor Company. The DMC 12 featured gull-wing doors, rust-proof, stainless steel panels, and a lightweight composite chassis designed for improved performance.

DeLorean also managed to convince the government of Northern Ireland to invest 85 million pounds in the operation. Additionally, he installed a state-of-the-art factory in Belfast, bringing 1,500 new jobs as well as economic optimism to an area mired by years of sectarian violence during “The Troubles.” At first, everything looked rosy as demand outpaced production for the futuristic-looking sports car. But underwhelming performance issues along with budget overruns and quality control quickly led to DeLorean’s own troubles and the desperate need for more quid. 

He then sped into an ill-advised road into the world of narcotics — an avenue he hoped would earn him a quick $24 million to keep DMC running. Instead, he plowed into a federal sting operation that targeted white-collar drug traffickers. Although video cameras caught him red-handed making a deal, he was later acquitted after his lawyers argued that FBI agents had entrapped the disgraced auto executive. Nonetheless, DMC quickly collapsed — sinking like another famous vessel built in Belfast: the Titanic.

9. John Gotti

Known as the “The Teflon Don” for his ability to avoid conviction, John Gotti ran the Gambino crime family in New York City with equal parts panache and blood-spattered violence. His well-coiffed hair and expensive suits reflected a highly successful operation that generated a rumoured annual income of $500 million. In the end, it took the combined efforts of a raging bull, the US Department of Justice, and the dogged pursuit of the FBI to finally bring Gotti down.

By the mid-1980s, Gotti had steadily climbed up the mafia’s chain of command. But his simmering beef with then Gambino head honcho, Paul Castellano, turned deadly when Castellano and other mobsters were shot dead outside of the swanky Sparks Steak House in Midtown Manhattan. Gotti, who had ordered the hit, soon took over and expanded into other criminal enterprises, including the highly profitable distribution of narcotics.

Although the fast and loose 80s saw Gotti walk free on three separate prosecutions, the 90s wouldn’t be as kind to the cocky mob boss. The FBI, aided by the US Assistant Attorney General, Robert Mueller, outwitted the racketeer’s unscrupulous, maniacal plans by flipping Salvatore “Sammy the Bull” Gravano in exchange for a more lenient stretch. On April 2, 1992, a jury found Gotti guilty on multiple charges ranging from obstruction of justice to tax evasion and was sentenced to life imprisonment without the possibility of parole. He later died of throat cancer in 2002. 

8. Pretty Boy Floyd

For any dreamer, the dusty plains of Oklahoma are a stark contrast to the bright lights of the big city, and the allure of greener pastures proved irresistible for Charles Arthur “Pretty Boy” Floyd. As yet another colorfully nicknamed gangster from the 1930s, he went on to commit a series of well-publicized bank robberies and murders throughout the Midwest.

To his credit, Floyd tried earning an honest wage while labouring as a roughneck in the oil fields near Tulsa. He often turned up wearing a white button-up dress shirt and slacks to work, prompting the men on the rig to call him “Pretty Boy” — a moniker he hated as such as the physically demanding work. 

Floyd gravitated towards the nefarious underbelly of Kansas City, where he partnered with other outlaws, including prolific bank robber, Frank “Jelly” Nest. Floyd’s association with these men proved both financially rewarding and deadly — culminating with the “Kansas City Massacre” — a mass shooting that shocked the nation and exposed the growing lawlessness in poverty-stricken America. 

When Nest was arrested in June of 1933, several of his felonious friends hatched a plan to set him free. Although accounts differ regarding which perpetrators were actually involved, a wild shootout at Union Station resulted in the death of the prisoner and four law enforcement officers.

Although Floyd denied taking part in the melee, it didn’t matter. He had been recently named “Public Enemy Number One” after the death of John Dillinger, and the FBI was determined to hunt him down. Similar to the account surrounding the ‘massacre’ story, at least three versions of Floyd’s demise later surfaced. Still, one fact remains irrefutable: Pretty Boy Floyd died after a shootout with FBI agents in East Liverpool, Ohio, on October 22, 1934.

7.  Machine Gun Kelly

In the spirit of Lady Macbeth, Kathryn Kelly was an ambitious woman determined to carve out a better life for herself by any means necessary. She found the ideal accomplice in her fourth husband, George Kelly Barnes, a small-time bootlegger from Memphis. As the story goes, the attractive femme fatale bought her hubby a Thompson machine gun and re-branded him “Machine Gun Kelly.” Unfortunately for them, checking into the grey bar hotel wasn’t part of the plan. 

In July 1933, the husband and wife team pulled off an elaborate scheme that yielded their biggest cash grab to date. They successfully kidnapped oil tycoon and businessman, Charles F. Urschel, from his home in Oklahoma City and soon collected a whopping ransom of $200,000.

But a subsequent FBI investigation resulted in their arrest 56 days later in Tennessee. The larcenous lovers then became jailbirds after being convicted and sentenced to life imprisonment. George served part of the all-day stretch at Alcatraz but died at the federal lockup in Leavenworth, Kansas in 1954. As for his beloved bride, Kathryn spent 25 years at a women’s correctional facility in Virginia before dying at the ripe age of 81. 

6. John Dillinger

As the FBI’s first “Public Enemy Number One,” John Dillinger reigned supreme among Depression-era desperados. He and his ruthless gang were accused of robbing 24 banks and four police arsenals, murdering 10 men, and staging three prison escapes. The Hell-raising Hoosier even managed to craft a reputation as a modern-day Robin Hood, giving the downtrodden masses an outlaw hero to cheer for during tough times.

John Herbert Dillinger was born into a middle-class family on June 22, 1903, in Indianapolis. He showed signs of deviant behaviour at an early age that grew increasingly violent throughout his life. Although Dillinger quit school at 16, he received an education of a different stripe while serving an eight-year jolt for robbery at the Indiana State Prison. There, he learned the ABCs of robbing banks from more seasoned pros — knowledge he quickly put to use after getting sprung in May 1933. 

Dillinger stayed busy over the next 14 months, plundering with his scary band of hardened ex-cons that included the likes of Harry “Pete” Pierpont, Homer Van Meter, and Baby Face Nelson. After successfully busting out of an ‘escape-proof’ pokey in Crown Point, Indiana, just outside of Chicago, Dillinger made the mistake of stealing a sheriff’s car and driving it to Illinois. His getaway had violated the National Motor Vehicle Theft Act, a federal offense involving the transportation of a stolen motor vehicle across state lines, and thus triggering a nationwide FBI search.  

Coincidentally, Dillinger’s luck finally ran out shortly in the summer of 1934 after watching Manhattan Melodrama — a movie about a popular, slick criminal. Spoiler alert: it doesn’t end well. A brothel madam named Ana Cumpanas had tipped off the Feds, who waited for the wanted man as he walked out of the Biograph Theatre in Chicago. Acting on instinct, Dillinger pulled out his pistol and attempted to flee down a nearby alley before being gunned down in a hail of bullets. 


5. Baby Face Nelson

Most armchair shrinks would probably agree that Lester Gillis suffered from severe psychological issues. His small stature and cherubic appearance didn’t exactly project a stone-cold killer, but that’s just what “Baby Face” Nelson became. Although he hated the sobriquet that made him a household name from coast to coast, he took satisfaction in killing more FBI agents than any other scofflaw in history. 

The pint-sized hoodlum began his life of crime in Chicago, spending most of his childhood in and out of juvenile reformatories. He eventually formed his own gang and engaged in petty theft and bootlegging before graduating to armed robbery. In addition to knocking over banks, the baby-faced bandit organised a series of brazen home invasions that included the home of Chicago mayor Big Bill Thompson.  

Nelson joined forces with John Dillinger’s gang in March of 1934. Shortly afterward, he shot Special Agent W. Carter Baum — the first of three federal agents Nelson killed that year and was later named “Public Enemy Number One.” His tenure as top dog, however, was short-lived. On November 27, 1934, a shootout occurred in Barrington, IL, resulting in the deaths of Nelson and two more FBI agents. 

4. Bonnie and Clyde

Love can be messy. And sometimes even downright bloody. Such was the case with Bonnie Parker and Clyde Barrow, a pair of star crossed crooks whose bullet-riddled bodies ended one of the most spectacular manhunts the nation had ever seen. 

During the Great Depression, high unemployment and a prevailing sense of hopelessness pushed countless, desperate citizens to pursue a life of crime. The dangers involved usually ended in death, but some people at least enjoyed the good times while they lasted. Although they didn’t possess the same movie-star looks of Warren Beaty and Faye Dunaway, the A-list actors portraying them in the 1967 blockbuster movie, the real-life Bonnie and Clyde lived large stealing cars and robbing banks during the early 1930s. But the thrill ride would come to a crashing halt during a FBI ambush in Bienville Parish, Louisiana.

The couple had been traveling in a stolen 1934 Ford sedan and armed with more than a dozen guns and several thousand rounds of ammunition, including 100 20-round BAR magazines. But they were no match for the heavily armed law enforcement posse as the G-Men unleashed a fury of gunfire into the car, leaving both fugitives dead on the scene. 

3. Al Capone

The defiance of federal Prohibition laws during the “Roaring ’20s” led to the rise of lucrative empires built on bootlegging that invariably also included extortion, gambling, prostitution, narcotics, and murder. In Chicago, a scar-faced gangster ran the Windy City as his own private fiefdom, crushing anyone who got in his way. The notorious boss would earn a slew of nicknames during his dastardly dynasty, but is best remembered as Al Capone

After cutting his teeth as a small time thug in his hometown of Brooklyn, Capone landed in Chicago in 1919, looking to make a name for himself. It didn’t take long. By the mid 1920s, he had become the de facto king of the local underworld and enjoyed the spotlight as a larger-than-life public figure. In 1929, he also showed off his romantic side by ordering the execution of several gangland rivals in the infamous St. Valentine Day’s Massacre.

Capone manipulated the system to avoid prosecution by sheer force and intimidation until the Feds finally nailed him on the humdrum crime of tax evasion. On October 18, 1931, the career criminal was convicted and sentenced to 11 years in federal prison. (Make no mistake: Eliot Ness and his Untouchables were part of the Treasury Department, but the FBI most definitely played a role in Capone’s eventual downfall.)

He spent most of his time locked up on Alcatraz, where his health rapidly deteriorated stemming from syphilis. After serving seven years, six months and 15 days, and having paid all fines and back taxes, he was released from prison. Capone then retreated to South Florida, where he died of a stroke and pneumonia on January 25, 1947.

2. Patty Hearst

The stranger-than-fiction tale of Patty Hearst had it all. Celebrity. Scandal. Crime. And even a fledgling revolutionary terrorist group for good measure. On February 4, 1974, members of a group calling themselves the Symbionese Liberation Army (SLA) kidnapped the granddaughter publishing magnate and politician William Randolph Hearst, the billionaire who famously served as the inspiration for Citizen Kane.

Patricia “Patty” Hearst was a 19-year-old college student when the incident occurred that would irrevocably change her life forever. Law enforcement frantically searched the country for her whereabouts for over two months while the Hearst family attempted to accommodate the SLA’s unusual demands. But then unexpectedly, she surfaced on security cameras holding a M-1 carbine while helping her comrades rob a bank. The bizarre turn of events marked just one of many twists and turns in the saga, involving the heiress who went from an unassuming art history major to landing on the FBI’s most-wanted list. 

She remained on the lam for nearly two years, actively taking part in other crimes with SLA under the alias of “Tania.” Finally, in September 1975, a combined task force of FBI agents and the San Francisco Police Department nabbed the fugitive as she walked out of her modest apartment in the city by the Bay. Hearst initially expressed solidarity for her captors. An article in Time Magazine reported, “At the San Mateo jail, Patty listed her occupation as “urban guerrilla.” Her lawyer, Terence Hallinan, told newsmen that she had asked him to relay a message to the public: “Tell everybody that I’m smiling, that I feel free and strong and I send my greetings and love to all the sisters and brothers out there.”

She later changed her tune, claiming she had been brainwashed and fallen victim to Stockholm syndrome, a psychological condition in which a captive develops sympathy or affection for their kidnappers as a survival strategy. She also hired the well-known criminal defence lawyer and boozehound, F. Lee Bailey, whose bungling of the case included spilling water all over his pants during closing arguments. 

Hearst was convicted of bank robbery and sentenced to 35 years in prison following a prolonged media circus trial. However, she served less than two years after President Jimmy Carter commuted her prison term in 1979. Since her release, she’s stayed busy with multiple endeavors, such as acting, writing, and as an award-winning participant in dog shows.

1. The Unabomber

On April 3, 1996, the FBI apprehended a disheveled 53-year-old man at his rural cabin in northeastern Montana. The arrest ended a nearly two-decade investigation — the most expensive in the Bureau’s history — for the enigmatic terrorist called the “Unabomber.”

Theodore John “Ted” Kaczynski exhibited early indications of a budding genius. He scored a 167 IQ at age 10 and five years later graduated from high school with honors. After earning a scholarship to Harvard, the gifted prodigy continued his tormented but remarkable academic ascent — especially in the field of complex analysis — and eventually joined the mathematics staff at the University of California, Berkeley. 

Meanwhile, Kaczynski grew increasingly withdrawn and resentful towards the trappings of an industrialized, modern society. He abruptly quit his teaching post in 1969, and soon retreated to the remote wilderness of Big Sky country, where he lived off the grid and meticulously plotted his revenge. From 1978 to 1995, Kaczynski carried out a sophisticated mail-bombing campaign, randomly killing three people and injuring 23 others. A total of 16 bombs were delivered — many containing cryptic clues — as he continued to thwart authorities and terrorize the nation.

The FBI had dubbed him “the Unabomber” because his early victims had been associated with universities or airlines. In 1995, the Feds received a break in the case when Kaczynski sent a typed 35,000-word ‘manifesto’ to the Washington Post and New York Times. Entitled “Industrial Society and Its Future,” the rambling tome expressed his muddled grievances and motives for the attacks. It would also lead authorities directly to the hermit’s hideout in the woods.

Kaczynski’s brother, David, had read the essay in the newspaper and immediately recognized it as the work of his estranged sibling. He then contacted the FBI and gave them the whereabouts of the Montana location. Although the ramshackle 10’ x 14’  hut lacked both electricity and running water, agents found an enormous cache of bomb-making materials as well over 40,000 handwritten journal pages detailing numerous crimes. Investigators also uncovered a particularly disturbing item hidden underneath a bed: an unsent package containing a live bomb. 

A federal grand jury indicted the prisoner on ten counts of illegally transporting, mailing, and using bombs, and three counts of murder. Renowned criminologist and forensic psychiatrist, Park Dietz, stated that Kaczynski wasn’t psychotic but had “a schizoid or schizotypal personality disorder.” After being declared fit to stand trial, Kaczynski pled guilty to all charges, thus avoiding the death penalty. He is currently serving eight life sentences without the possibility of parole at ADX Florence, a maximum-security facility in Florence, Colorado — aka the “Alcatraz of the Rockies.”


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