You can choose your friends, but you can't choose your family -- no matter how badly you wish you could, or how much you pay your publicist to try. Some celebrities (both of the famous and the infamous variety) have led lives so directly opposed to their family members that they may as well be from alternate universes. Such as ...
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James "Whitey" Bulger was king of the Boston underworld between the 1980s and 1990s, an Irish Mob kingpin most recently portrayed on screen by Johnny Depp buried deep under a pile of ridiculous prosthetics.
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It's still the least makeup he's worn onscreen since 2002.
While Whitey was racketeering his way through the Boston underworld and earning a place on the FBI Most Wanted list, his brother, William "Bill" Bulger, was enjoying a successful career of quite a different kind -- as the longest-serving president of the Massachusetts Senate.
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"I am not a crook ... No, really. I am not a crook."
According to those who knew them both, the Bulger brothers grew up with very similar traits -- both highly intelligent authoritarians who intimidated their way to the top. But, while Whitey put his skills to bank robbery and mob politics, his brother Bill put those same skills to actual politics. They both achieved the same result, albeit on opposite sides of the law.
Bill Bulger has always distanced himself from his brother, but never turned on him. And it cost him two careers -- in 2003, he was forced to resign from his position as president of the University Of Massachusetts after refusing to testify against Whitey, and suffered another blow to his political career in 2013 when Whitey was ultimately convicted of his crimes and Bill said nothing except that he still loved his brother. And you thought your relatives were a burden.
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The Whitey man's burden.
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Possibly the most famous Mafia boss of all time, Al Capone rose to the top of the Chicago Mob during the Prohibition era, where he earned his wealth and notoriety supplying thousands of tragically sober Americans with the most illegal and delicious of drugs: alcohol.
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"The cause of, and solution to, all of the Constitution's amendments."
Capone's oldest brother was James Capone, who later changed his name to James Hart in order to hide his family ties. That was a good move because James was looking at a career in law enforcement, specifically as a Prohibition agent, locking away his brother's own loyal customers for a living.
James was such a headkicker for Prohibition that he earned the nickname "Two-Gun Hart," which he embraced in the most ridiculous fashion by dressing in a comically absurd cowboy costume.
Which confusingly had just one gun.
During the summer of 1927, Hart got a job as President Calvin Coolidge's personal bodyguard. He was so deeply incognito that neither his family nor the government knew that the man they tasked with protecting the commander in chief was the brother of the most notorious criminal in the United States.
In the late 1930s, after Prohibition had been repealed, James finally had a crisis of familial relations and decided to contact his family. He never got in touch with Al, but reconnected with his other brothers, John and Ralph. This proved to be a mistake because Ralph, while not as criminal as Al, was actively engaged in a tax evasion scam, falsely naming other family members as the owners of his own properties.
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Tax evasion: the Capone kryptonite.
The IRS was already suspicious, so when James Hart's name turned up as the owner of one of Ralph's businesses (without James's consent), the government finally connected the dots. When it hit the media, Two-Gun Hart's career dissipated like a Two-Bun Fart.
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Journalist and philosopher Christopher Hitchens made a career out of having strong opinions about things, but he was perhaps best known for his powerful condemnation of any and all religion, publishing a number of books about atheism well after Richard Dawkins made it cool.
He died in 2011 following a short battle with a lightning bolt.
Christopher's younger brother, Peter Hitchens, also followed the family trade into journalism. But, unlike Christopher, Peter is both a Christian and a Conservative. Both Hitchens brothers grew up as staunch atheist communists, but, over time, their beliefs began to diverge. Peter now considers himself a Christian "paleoconservative" and views his former hard-left political views as a "disease" that had infected him.
The schism between the two Hitchens brothers was so great that they actually held a formal debate, which you can watch if you have two spare hours and absolutely hate your free time:
Shortly before Christopher died, Peter wrote his own book, The Rage Against God, which was, in part, a refutation of his brother's work. The effort nearly brought the brothers to blows, and Peter vowed never again to directly confront Christopher on his views. Luckily for him, that's only likely if Christopher was wrong, anyway ...
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Fidel Castro, after taking over the government of Cuba in the 1970s, has served ... let's just say, a few terms as president. Officially, he retired from the role in 2008, but it's unknown whether he really stopped running the country or just stepped back into a more Vladimir Putin/Joe Jackson kind of role.
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"If Walt Disney can still run Florida, I can keep running Cuba."
Fidel's younger sister, Juanita Castro, defected to the United States in 1964 and spent the next few years providing intelligence against Fidel through the two most significant U.S./Cuba conflicts: the Bay Of Pigs Invasion and the Cuban Missile Crisis.
In fact, she became such a well-respected voice of anti-communist sentiment during the Cold War that the CIA personally dispatched her to Chile during its revolutionary phase in order to warn its populace about submitting to communism. The campaign was successful, and Chile rejected the communists in favor of ... well, Augusto Pinochet and decades of death squads. But, it's uh ... the thought that counts?
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That thought being, "better dead, than red."
During the 1960s, Juanita lived the life of a secret agent, smuggling documents to and from Cuba and personally sheltering fugitives of the Cuban Secret Police. In a slightly more insane plot, she even helped release a swarm of fruit flies into Cuba in an effort to destabilize their agriculture. Sometimes, war is hell, and sometimes, it's just really annoying.
After the Iron Curtain fell and relations between the U.S. and Cuba started to improve, Juanita settled into a regular life more befitting the American Dream: She ran a pharmacy business in Miami. Eventually, she went on to publish a memoir that revealed her secret life for the first time and presumably never commented on the irony of rejecting Cuban health care to open a pharmacy in the United States.
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Reinhard Heydrich was an officer in the SS (those are Nazis, if you didn't know; Nazis are bad guys, if you didn't know -- you really should know, though). He was so brutal that he earned the nickname "The Butcher Of Prague."
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He stole the title from Konrad, a Bohemian sausage vendor.
Reinhard and his brother Heinz were both enthusiastic supporters of the Third Reich and Hitler's revolutionary "let's kill everyone who looks even slightly different from me" presidential campaign.
The loved every presidential murder debate on Nazi CNN.
Reinhard was an early recruit to the SS and rose through the ranks over the years. He helped orchestrate Kristallnacht and eventually its big budget sequel: the Holocaust. He was assassinated in 1942 by militants who thought the Holocaust was a bad idea, for reasons they didn't feel needed explaining.
Heinz, upon discovering that Hitler's "murder everyone" platform wasn't some kind of metaphor, completely changed his position. As a journalist, he became increasingly critical of the Nazi regime and eventually went full hog against the Third Reich, helping to forge a hundred passports for Jews, allowing them to escape Europe and the Holocaust. Heinz Heydrich committed suicide in 1944 when he suspected that the Gestapo were on to him, though they likely still had no idea and simply wanted to question him for wasting paper. To be fair to Heinz though, they would probably still kill you for that. Nazis weren't super chill.
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Benjamin Franklin. You know him from creating America, inventing half of the technology you use today, fucking his way through all 50 states, and the goddamn $100 bill. Yes, he is what it's all about.
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"I keep it 100 all day, every day. Literally."
Ben Franklin had an illegitimate son named William. Due to Ben's power and influence, William became governor of New Jersey, which we guess is slightly better than governor of nothing. But, when the American Revolution broke out, there were some awkward conversations at the Franklin family dinner table. William Franklin was a hardcore loyalist to the British crown.
Even when it became apparent that England was going to lose, William Franklin refused the command to defect to the United States and, instead, escaped to London. But, he didn't go quietly -- once he was comfortably back in England, William Franklin convinced the British to launch another attack on the not-quite-yet-United States, which again failed. He died in 1813, after his father had signed the constitution he dreaded ever coming to pass.
As a final note of irony, William's son, also named William (apparently there just weren't many names back in the day), defected again against his own father and became a diplomat for his grandpa, Ben Franklin. All teenagers go through a rebellious phase, but when the Franklins rebel, they rebel hard.
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