#2. The Brother of One of the World's Richest Men, Jefri Bolkiah
Before Bill Gates starting taking the title of World's Richest Man every year, the title usually went to the Sultan of Brunei, Hassanal Bolkiah. In 2009 he made the list of the world's richest royals with a net worth of $20 billion.
And $2.8 billion in shiny medals.
He's called the Sultan of Brunei because Brunei is a small country in Southeast Asia on the island of Borneo, made insanely rich by, you guessed it, oil and natural gas. And like many countries that control vast amounts of resources, Brunei is family owned, in this case by a sultanship. Which means any family member can fill any important government position.
You can guess where this is going.
The Sultan of Brunei's brother Jefri Bolkiah was a bit of a troublemaker. Initially he got into the press due to his escapades with his harem of over 40 women. Eventually things got embarrassing enough that the sultan gave him the job of finance minister, just to keep him out of the papers (because who cares about the minister of finance?), thinking he couldn't do any real damage there.
If your brother sports a porn-stache, just assume the worst no matter what.
Afterward he went on the kind of spending spree that only a billionaire could manage. Jefri didn't buy luxuyry goods -- he bought entire luxury goods stores. Also, fleets of cars and airplanes, yachts, chains of hotels, etc. He even flew women into Brunei to sexually abuse. Nice guy.
After the Asian markets collapsed in the late 1990s, Brunei's accountants soon noticed the $14 billion and followed the trail to Prince Jefri.
And by trail, we mean row after row of luxury yachts clogging up the harbor.
Naturally the sultan got pissed when he found out Jefri had siphoned a good 10 percent or so of the country's funds over the course of 12 years. The sultan tried to grab him before other countries or fellow Brunei citizens could, but Jefri skipped the country. So Hassanal simply banned him from the country for the next decade, with Jefri not being allowed back until 2009. After all, what's a little $14 billion among family?
The United States and United Kingdom brought several court cases, costing Brunei millions more to settle lawsuits caused by Jefri's misdoings. Brunei's reputation was ruined, the sultan still loses millions each year and Jefri is currently under virtual house arrest for pretty much the biggest embezzling job in history. Most importantly, though, this has probably led to some of the most awkward family dinners ever.
Via Daily Mail
"Sorry, guys, but I ate all the food that I didn't already fuck."
#1. Albert Goering, Brother of Hitler's Right-Hand Man, Hermann Goering
So let's turn this on its head for a moment. What happens when the powerful sibling is an asshole? Like, say, a high-ranking member of a fascist regime? How can a screw-up brother throw a wrench in that? By being too nice?
In the 1930s, the Nazis stormed into power in Germany and quickly set up shop. As a result, all of Adolf Hitler's buddies soon got top jobs, including Hermann Goering, who quickly moved up the ranks from head of the German Air Force in 1935 to being Hitler's number one man in 1941. Things were working out well for Hermann, except for two small things: The Allies quickly fighting back against German advances, and his fuckup brother, Albert Goering.
Via Daily Mail
He's the one with the mustache.
Unlike big brother Hermann, Albert wasn't exactly a fan of Nazis. In fact, he hated Nazism, particularly because of all the violent tactics Nazis used against people who opposed them, but also because it was possible his dad was Jewish (a Jewish aristocrat banged his mother about a year before he was born, and Albert looked a lot like him).
Assuming his godfather loved cigarette holders and had an ultra-smooth forehead.
So, Albert started doing some decidedly un-Nazi things. When some Jewish women were forced to clean a street, he went down and started helping them. And when a German officer stopped him and immediately recognized him as the brother of Hitler's right-hand man, he had everyone stop and go home.
Another time, when his Jewish mentor in business, Oskar Pilzner, was sent to a concentration camp, he used his brother's name to not just get Pilzner and his family set free, but also sent them out of Germany. When Hermann heard about what Albert did, he kept it quiet from his temperamental boss and stuck his brother at a small position at a factory outside of Germany so he couldn't cause any more good deeds for humanity.
"'Brother?' I don't have a brother. Is that even a real word?"
Despite being relocated as a director of a remote Czechoslovakian factory, Albert still caused a lot of trouble by working even more aggressively against his country. He actually teamed up with the Czech resistance and helped sabotage his own factory while also forging his brother's signature on transit papers to help countless more Jews and dissidents escape out of Nazi-controlled territory. When he was caught doing this, all he had to do was phone up his brother, who bailed him out, much to Hermann's annoyance. And most famously, he sent for workers from concentration camps, where he then ordered the trucks on the way back to "mysteriously" break down, allowing the people to escape.
After the war, he was almost convicted of war crimes and was imprisoned for many years just because of his name, but so many of the Jewish survivors he saved came to his defense that he was let go. This was not the same for Hermann, the brother he pissed off numerous times. Hermann committed suicide during his trial in 1946.
"Screw you, Evil, I do what I want. You are not the boss of me."
As for Albert, he would go on to live a quiet and difficult life. But we like to think his final act summed him up: He was getting old and close to death, and he wanted to do something nice for his housekeeper. So he married her ... just so that when he died, she would keep getting a pension check as his widow.