History History 5 min read

Did Frank Sinatra really act as a secret liaison between JFK and the mob?

Image: Fresnel

From cinematic prison escapes to strange personal habits, the real history of 20th-century organized crime is stranger than fiction. Figures like Al Capone, John Dillinger, and Bugsy Siegel built reputations on ruthlessness; yet, their private lives were filled with bizarre quirks, peculiar superstitions, and unbelievable historical twists. Discover 10 real gangster tales you won’t believe are true.

1
Frank Sinatra was punished by the mob over JFK

Image: mark reinstein

According to reports, during the 1960 presidential election, Frank Sinatra allegedly acted as an intermediary connecting Chicago Outfit boss Sam Giancana with John F. Kennedy’s campaign. The mob believed securing votes for JFK would lead to lighter law enforcement pressure on organized crime.

When President Kennedy and Attorney General Robert Kennedy instead launched an aggressive crackdown on the Mafia, Giancana blamed Sinatra for failing to deliver on implied promises. As punishment, Giancana is said to have forced Sinatra to perform eight consecutive nights of unpaid shows at his Villa Venice nightclub in suburban Chicago to make up for the betrayal.

2
Al Capone opened one of America’s first Great Depression soup kitchens

Image: National Archives at College Park, Public domain, via Wikimedia Commons

In November 1930, as the Great Depression devastated the American economy, Chicago mob boss Al Capone saw an opportunity to improve his public image by opening a soup kitchen. Operating out of a storefront at 935 South State Street, Capone’s establishment served three hot meals a day (including coffee, soup, and donuts) to over 2,200 unemployed people daily.

Capone funded the operation entirely out of pocket with no government assistance, earning him a reputation among many locals as a modern Robin Hood before his tax evasion conviction.

3
Prohibition moonshiners wore "Cow Shoes" to fool the law

Image: National Photo Company Collection, Public domain, via Wikimedia Commons

During Prohibition, federal agents and state police tracked illegal distilleries by following human footprints through soft mud and dirt. To counter this, rural bootleggers invented "cow shoes".

These specialized footwear attachments consisted of a carved wooden block shaped like a cow’s hoof at the bottom. When moonshiners walked through the woods carrying heavy jugs of illegal liquor, they left behind tracks that looked like cattle rather than criminals.

4
John Dillinger escaped jail with a block of wood

Image: Indiana State Penitentiary, Public domain, via Wikimedia Commons

In March 1934, infamous bank robber John Dillinger was locked inside the Lake County Jail in Crown Point, Indiana, a facility local officials bragged was completely impossible to escape from.

Using a pocketknife, Dillinger carved a piece of wood into the shape of an automatic pistol and stained it black using razor polish. He used the wooden prop to trick a guard into opening his cell door. After taking real weapons from the jail armory, Dillinger took hostages and stole the sheriff’s personal V8 Ford to make his getaway.

5
The "Oddfather" wandered New York in pajamas for 30 years

Image: National Archives at College Park, Public domain, via Wikimedia Commons

Vincent "Chin" Gigante, boss of New York’s powerful Genovese crime family, earned the nickname "The Oddfather" for his elaborate scheme to evade federal prosecution. Starting in the late 1960s, Gigante began wandering the streets of Greenwich Village wearing a ragged bathrobe, pajamas, and slippers while muttering incoherently to himself.

His lawyers presented him as suffering from severe dementia and schizophrenia. For nearly three decades, the performance protected him from trial. However, in 1997, federal prosecutors finally proved in court that the routine was an act, and Gigante admitted in 2003, at age 75, that his madness was fake.

6
Al Capone accidentally shot himself in the groin

Image: Miami Police Department, Public domain, via Wikimedia Commons

Despite his reputation as a ruthless gang boss, Al Capone was surprisingly clumsy with his own weapons. In September 1928, while playing a round of golf at the Burnham Woods course near Chicago, Capone reached into his pocket to retrieve a golf ball.

His hand caught the trigger of his hidden, loaded revolver. The gun discharged, shooting Capone through the right thigh and groin. He was rushed to Saint Mary’s Hospital under the alias "Bob Hart" and spent weeks recovering from the self-inflicted wound.

7
FDR rode in Al Capone’s armored limousine?

Image: kukurund

Following the Japanese attack on Pearl Harbor on December 7, 1941, the Secret Service faced an immediate security dilemma: President Franklin D. Roosevelt needed a bulletproof vehicle for his public appearances, but federal rules prohibited spending more than $750 (or about $17,000 today) on executive automobiles.

According to legend, Treasury agents solved the problem by pulling Al Capone’s custom 1928 Cadillac Town Sedan out of impound. The car had been seized by the government following Capone’s tax evasion trial in 1931. Equipped with heavy armor plating and bulletproof glass, Capone’s former car might have safely transported President Roosevelt to Capitol Hill to deliver his famous "Day of Infamy" speech.

8
Kingpin Arnold Rothstein never drank alcohol

Image: Unknown /w New York Times, Public domain, via Wikimedia Commons

Arnold "The Brain" Rothstein was the financial mastermind of 1920s American organized crime, famously transforming street gangs into corporate syndicates and allegedly fixing the 1919 World Series.

Despite making tens of millions of dollars importing illegal liquor during Prohibition, Rothstein was a strict teetotaler. He never drank alcohol, smoked cigarettes, or used drugs. Instead, he preferred milk, ginger ale, and club soda, maintaining that staying sober gave him a clear advantage over business rivals and gamblers.

9
Bugsy Siegel tried to fix his hairline with magic

Image: New York Police Department, Public domain, via Wikimedia Commons

Benjamin "Bugsy" Siegel, the mobster credited with developing the Flamingo Hotel and building modern Las Vegas, was notoriously vain. Obsessed with his good looks, Siegel loathed his nickname "Bugsy" (slang for crazy) and lived in terror of going bald.

As his hairline began to recede, Siegel turned to extreme measures. He bought expensive unproven tonics, tried home remedies involving raw eggs and olive oil, and consulted spiritualists who offered magical chants and scalp massages to restore his hair growth.

10
Mickey Cohen was a devoted dog dad and germaphobe

Image: Larry Downing, Los Angeles Times, CC BY 4.0, via Wikimedia Commons

West Coast mob boss Mickey Cohen ruled Los Angeles crime with an iron fist, but his personal life was defined by extreme eccentricities. Cohen was a germaphobe who washed his hands dozens of times a day and refused to touch doorknobs without a towel.

At the same time, Cohen was a passionate dog lover. He showered his pet dogs with affection, buying them silk bedding, feeding them prime cuts of meat, and hiring full-time staff to groom and walk them. When his favorite dogs fell ill, Cohen hired top veterinary specialists to tend them at his Hollywood home.

Geography Geography 6 min read

Territorial anomalies

There's a country within the US that was created to avoid double taxation

Image: Pin Adventure Map

Ever thought about how the borders in our country were defined ? States that almost became official, U.S. points that are only accessible through Canada's borders, territorial feuds over taxes, and more have constructed the limits of the country we know today. Here are 10 territorial quirks you probably never knew of.

1
Point Roberts, WA: The 49th parallel accident

Image: United States Geological Survey, Public domain, via Wikimedia Commons

Imagine if you had to cross two borders just to get to the market for a gallon of milk. That’s actually a reality for residents of Point Roberts, Washington. That’s because, following the Anglo-American Convention of 1818, the 49th parallel divided Canada and the U.S. In 1846, the line was extended westward and then officially recognized by the International Boundary Commission in 1925.

However, a tiny tip of the Tsawwassen Peninsula poked out just below that line. Since then, the locals have lived in a boundary quirk. To get to the rest of Washington State by land, they must drive through Canada, show their passports, and do it all over again on the way back.

2
Statue of Liberty: Common misconception

Image: Mohamed Osama

If you want to start a friendly argument at a dinner party, ask whether the Statue of Liberty lives in New York or New Jersey. The funny thing is, both answers are technically right . While the statue physically sits in the waters of the Garden State, Liberty Island is legally an exclave of New York. This dates back to a 1664 land grant by the Duke of York in a document so vague and confusing that it took a 1834 Compact between the two states to settle the deal. New Jersey gets the water and the submerged lands, but New York keeps the monument.

However, the Federal Government actually manages the site through the National Park Service (NPS), providing security and maintenance.

3
The State of Franklin: Failed 14th state

Image: Bennett1203, CC BY-SA 4.0, via Wikimedia Commons

In 1784, three counties in North Carolina felt neglected by their government and decided to strike out on their own . They even elected a governor, John Sevier, and printed their own money. They came just two votes short of being recognized by Congress as a formal state.

Eventually, things got heated, and North Carolina sent troops, leading to a small civil war between the locals. By 1789, the dream of Franklin was buried, and the territory became part of Tennessee.

4
Kentucky Bend

Image: Brian Stansberry, CC BY 4.0, via Wikimedia Commons

If you look closely at a map, there’s a piece of Kentucky that looks like it doesn’t belong. That’s the Kentucky Bend, also called the New Madrid Bend, a tiny peninsula in Fulton County that is almost completely separated from the rest of the Bluegrass State . The strange situation was the consequence of the massive series of earthquakes that took place in that area between 1811 and 1812, which were so violent they famously caused the Mississippi River to flow backwards for several hours. When the dust settled, the river had carved a new path that looped around this small patch of land, surrounded by Missouri and Tennessee instead of Kentucky. The 9 residents living there today go through Tennessee just to get to their home state.

5
The State of Deseret: The empire that almost was

Image: Carl Radefeld (cartographer); Joseph Meyer (publisher), Public domain, via Wikimedia Commons

Imagine a state so big it makes Texas look tiny. That almost happened back in 1894, when Mormon pioneers proposed the State of Deseret. The territory comprised what we now know as Utah, most of Nevada, parts of Arizona and Colorado, and a massive chunk of the California coast, including San Diego.

Had it been formalized, it would have been a powerhouse with its own seaport and total control over the West. However, Washington, D.C. wasn’t so keen on one group having that much territory and power, so they whittled it down, and we ended up having the states we know today.

6
The lawless "No Man's Land"

Image: Steve Shook from Moscow, Idaho, USA, CC BY 2.0, via Wikimedia Commons

Have you ever wondered what happens when two governments simply give up on a piece of land? Between 1806 and 1821, there was a strip of land in what is now western Louisiana that was, literally, No Man’s Land. Neither the U.S. nor Spain, which owned part of the territory, could agree on the border, so they declared it "Neutral Ground" to avoid armed conflicts . The plan backfired as, with no laws to contain it, it quickly became a favorite for the outlaws in the West —meaning deserters and bandits hiding there were legally untouchable. The conflict was resolved by the 1819 Adams-Onis Treaty, which officially set the Sabine River as the legal boundary.

7
The Republic of the Indian Stream

Image: Jon Platek, CC BY-SA 3.0, via Wikimedia Commons

In the early 1830s, people living in a small area between New Hampshire and Quebec were fed up, and in this case, taxes were the problem. Both Canada and the US were trying to collect taxes, and nobody likes being double-billed . In 1832, the residents essentially said "neither of them can tax us" and formed their own country called the Republic of the Indian Stream. They had their own constitution and Capitol for four years, until 1836, when the militia marched on the disputed territory to reclaim the land. It wasn’t until 1842, when the land dispute and the double taxation were definitively resolved by the Webster–Ashburton Treaty, which assigned the land to New Hampshire.

8
The Northwest Angle: Mapping mistake of 1783

Image: Lorie Shaull, CC BY-SA 4.0, via Wikimedia Commons

When the Treaty of Paris was signed in 1783 to end the Revolutionary War, the mapmakers used a chart that was flat-out wrong. They thought the Mississippi River started much further north than it actually did. Because of that mistake, a piece of Minnesota got cut off from the rest of the country . To this day, the "Northwest Angle" is the only place in the lower 48 states north of the 49th parallel. Much like Point Roberts, you have to cross a massive lake or drive through Canada just to visit it.

9
The District of Columbia’s "lost" corner

Image: Tim Mossholder

If you look at a map of D.C., you’ll notice it’s missing a chunk; it’s not a perfect square as it was originally intended. Originally, the capital was a perfect ten-mile square diamond , taking land from both Maryland and Virginia. But by 1846, things got tense. Residents in the Virginia portion, which included Alexandria and Arlington, were worried the federal government would abolish slavery in the District, which was the backbone of their economy. They successfully petitioned to have Virginia "take back" that portion of the land and subsequently changed the shape of the national capital forever.

10
UN Headquarters: International territory

Image: LPulecio-WMF, CC BY 4.0, via Wikimedia Commons

If you want to feel international, go to the United Nations Headquarters on the East River in midtown Manhattan, New York. Once you cross that gate onto the 18-acre site, you are technically leaving the United States. You don’t need to show your passport, but that’s international territory, which means it has its own laws , its own security force, and even its own postal service. It is a legal hole in the middle of New York City.

General General 4 min read

American uniqueness

10 things America does differently from the rest of the world

Image: Shamblen Studios

The U.S. is a unique country in many ways , but some of these might shock tourists and foreigners because they differ from how they are done in other parts of the world. From etiquette rules to cooking styles to how to record a date, America has its own way of doing certain things . Let’s have a look at some of them!

1
Measuring

Image: Annie Spratt

This is a difference most Americans are aware of: most countries use the metric system rather than U.S. customary units, and most use Celsius instead of Fahrenheit. Countries such as the UK and Canada still use some imperial units in everyday life, but they mainly use the metric system. Another measure that confuses foreigners is the particular way ingredients are measured in American recipes, which often use cups, tablespoons, and teaspoons rather than measurements by weight.

Fun fact: The only other countries that use the Imperial system officially are Liberia and Myanmar.

2
Sales tax

Image: Zoshua Colah

Do you find having to calculate sales taxes annoying? That’s a unique American experience. In the majority of the world, the price you see is the price you pay , because it has the sales tax already added.

Why is it different in America? Sales taxes vary across states , so retailers find it easier to showcase the base price and then calculate the total at checkout.

3
Cutlery use

Image: Anna Kumpan

Many Americans abroad are surprised by the realization that not everyone uses a knife and fork in the same way they do . In fact, no one else does. While most Americans have learned the American style —also called the zig-zag or fork switching method— that involves using the fork in the left hand for cutting and then changing it to the right to pick up the food, European and Latin American countries don’t do this . It might seem like a small difference, but it completely changes the way you eat.

4
Iced drinks

Image: Battlecreek Coffee Roasters

Do other countries not have ice? They do, but they don’t necessarily assume everyone will want it. While serving water and other beverages with ice is customary in America, in many other countries, you need to request it —even during the hottest of summers.

But even if you get ice, many times you will need to specify the amount : the same drink that would be filled with ice cubes in America might come to you with just two or three cubes elsewhere.

5
Date formatting

Image: Waldemar

The U.S. is not completely alone on this one, but there’s a difference big enough to be worth mentioning. The standardized way of recording the date in America is month-day-year , a convention also followed by some Caribbean and Asian countries. But in the rest of the Western world, the conventional format is day-month-year , which can lead to confusion for Americans. In most Asian countries , the most commonly used format is year-month-day .

6
The word ‘American’

Image: frank mckenna

In the English language, ‘American’ is the only way to refer to people with U.S. citizenship . Other words, such as ‘Usian’ or ‘Unitedstatian’ have been proposed, but never stuck. This is why many Americans are surprised when other countries —Latin American countries in particular— use ‘American’ for anyone in the American continent , or continents, another big difference. In most European and Latin American countries, there is a different word for U.S. citizens, such as the Spanish ‘estadounidense’ or the Portuguese ‘estadunidense’ .

7
Moving out at 18 years old

Image: Dina Badamshina

This one is not so black and white, but more like a general tendency. Compared with most of Europe, Latin America, and Asia, Americans give serious consideration to the possibility of moving out after high school. Not everyone does, and not everyone can afford it, but it's fairly common.

In other countries, young adults generally move out if their job or education requires it , but they tend to stay at home a few more years if they can.

8
Driving a car as a teenager

Image: Dan Gold

America is quite car-centric , especially if you live outside of the big cities. While not everyone can afford to have a personal car —even a second-hand one—, it is common for 16 and 17-year-olds to legally drive their parents’ car, or save for their own.

In the rest of the world, the chances of high schoolers driving themselves to school are much lower, as most countries don’t allow underage kids to get a driving license .

9
Solo cups

Image: Artem Beliaikin

Do plastic cups exist outside of the U.S.? They do, but they are not as iconic or as widely used as Solo cups, introduced in the 1970s as a disposable but sturdy cup for parties and events. Many foreigners visiting America are surprised when they realize that solo cups are a real thing , and not something that just happens in movies.

10
Filing taxes

Image: Olga DeLawrence

Taxes in the U.S. are not that different from taxes in other countries, except for how they are filed . During tax filing season, thousands of Americans direct their efforts to ensure they have properly reported their income and that their return will match the IRS’s data.

In other parts of the world, however, the one responsible for calculating and filing taxes is the government , while citizens merely corroborate that everything is in order.

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