Think that your sibling is embarrassing? That’s nothing compared to these brothers and sisters. I mean, take Al Capone’s brother Vince, for example. Could you imagine how mortified Scarface was when he learned what his brother was up to? I mean, he’s got a gangster image to keep up and all:

In most families, Al would be the embarrassment. However, while he was out making a success of himself by criminal means, his brother “Vince” ran away from home to join the circus, fought in WWI, and eventually became a policeman. Not in Illinois obviously, that would be a conflict of interest. In Nebraska. Vince spent Prohibition shutting down the same type of illegal alcohol productions that were making his brother rich and powerful. He was known as “Two-Gun Hart” and became famous in the Midwest for his law enforcement prowess. Al Capone must have been mortified.

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Al Capone’s business card claimed he was a used furniture dealer. He used the “I’m just a secondhand furniture salesman” line for years and finally had business cards printed up to hand out to police and investigators. For a used furniture salesman, he was doing pretty well – his annual income often exceeded $100 million. For that kind of money, I think I might go open an antique store…

Louie Bagels, AKA Louis Daidone, a member of the Lucchese crime family, apparently once spent his days kneading dough and filling vats of cream cheese at Bagels by the Bay in Howard Beach, Queens. As you can probably deduce, that’s how Louis got his mobster nickname.

You might remember Frank Sheeran from the Jimmy Hoffa saga – one of the many theories floating around is that Sheeran was used to get Hoffa in the car that would take him to his death. Hoffa and Sheeran were good friends and it’s widely believed that Hoffa wouldn’t have put himself in harm’s way without a trusted ally along for the ride. Before Sheeran was rubbing elbows with the likes of Hoffa, he was making money as a trucker. It didn’t take long for him to discover that he could be making a lot more money by committing some crimes along the way, including murder.

Albert Anastasia was a pretty bad dude. He ran a gang of contract killers called Murder Inc., and was once the boss of the Gambino family. But that’s not what his business card would have you believe. According to his card, Umberto Anastasio (his name at birth) was simply a lowly mattress salesman at Convertible Mattress Corporation in Brooklyn, New York. Something tells me he couldn’t have given you much advice on Serta vs. Sealy, though.

William Daddano, Sr., AKA Willie Potatoes, actually did have a legit company, not just a phony business card. By night, Daddano may have been a top enforcer with the Chicago Outfit. But by day, he was busy running the West Suburban Scavenger Service, a Chicagoland garbage collection company.

Harry J. “Doc” Sagansky could have made his mother proud – he actually had a degree in dentistry from Tufts University. He opened a practice in a liquor store in the pre-Prohibition days (liquor, dentistry… they go hand-in-hand, don’t you think?), which is where he got his feet wet in the life of illegal crime. It started with illegal gambling, which he used to fund a couple of nightclubs and a loan agency. He was quite successful and never had to return to dentistry as his day job, but he did continue making donations to Tufts and to Beth Israel Hospital for the rest of his life. In fact, he died at Beth Israel in 1997.

Bugsy Siegel, of course, was pretty instrumental in the development of Las Vegas as we know it today. First he bought the El Cortez on Fremont Street and ended up selling it for a profit of $166,000. Then he used that money to “convince” the owner of the Flamingo, which was in the planning stages, to accept new partners. He basically took a controlling stake and closely oversaw final stages of construction, even though he really had no idea what he was doing. He spent way too much money and got angry with his construction foreman, who was a little worried that his mobster boss was going to off him if things didn’t shape up. Reportedly, Siegel told him, “Don’t worry, we only kill each other.” I’m not sure I would be too reassured by that, really. The hotel opened on December 26, 1946, but Bugsy’s “legit” job didn’t last long – he was shot to death on June 20, 1947.

Apparently used furniture was an inside joke among mobsters, because it seems to be chosen as a “profession” more than any other, perhaps thanks to Al Capone. Joey “Doves” Aiuppa managed Taylor & Company, which was supposedly a furniture manufacturer, but was really just a front for a company that made illegal slot machines. “Doves” got his nickname because of all the things he could have been busted for over the years, the crime that landed him in jail was smuggling doves across state lines. It’s illegal to have more than 24 doves on your person outside of hunting season (who knew?), but in 1962, Aiuppa was caught by FBI agents with 563 frozen doves in his car and went to jail for three months.

Joseph Massino, who was once the head of the Bonanno crime family, was a restauranteur. He owned CasaBlanca Restaurant and catering in Queens (as well as several other eateries) We know for sure that he arranged for meetings at CasaBlanca, but Time magazine will only say that Massino allegedly ran an operation that included extortion, loan sharking, illegal gambling, narcotics and murder from the kitschy restaurant.

And then there’s the Pizza Connection. It was a massive Mafia plot to sell and distribute heroin and the cover for the entire thing were a bunch of independently-owned pizza parlors. The main one was located in Queens and was called “Al Dentes.” It reminds me of Loverboy, that old Patrick Dempsey movie where women could order a gigolo by requesting “extra anchovies.” The case cost more than $50 million and made prosecution lawyer Rudy Giuliani a highly sought after attorney.

Since today’s the anniversary of Dillinger’s demise, I thought it would be appropriate to revisit how some of America’s most notorious gangsters were finally brought down. We’ll start with Mr. Dillinger himself.

John Dillinger

From there, the duo went back to Indiana and stayed with his father for a while, then Dillinger robbed another bank in Indiana, then moved on to upper Michigan, then settled down at the Little Bohemia Lodge near Rhinelander, Wisconsin. Another shootout occurred at the Little Bohemia, but Dillinger evaded them yet again.

It wasn’t until July 21, 1934, that the infamous woman in red (who was actually wearing orange) contacted officers with the information that she and a “girlfriend of hers,” according to the FBI, although the “girlfriend” was probably a fellow prostitute, would be attending the movies with Dillinger on July 22. She offered the information in exchange for assurance that they would try to stop her deportation, which was currently under way. They also told her that she would receive a $10,000 reward if he was captured, which was clearly stated on the wanted poster. This deal sounded good to her, and she followed up with agents the next day to let them know that they would be attending one of two theaters: either the Biograph or the Marbro. Agents were set up to stake out each place, and at 8:30 p.m. on July 22, as promised, the trio strolled into the Biograph Theater to see Manhattan Melodrama starring Clark Gable.

J. Edgar Hoover instructed his men not to follow them in because of all of the innocent bystanders that could be hit, so they waited until the movie got out at 10:30. As soon as they exited the building, Melvin Purvis, Special Agent in charge of the Chicago office, lit a cigar to signal to his men that it was time to close in. Well, he tried to – he had trouble getting it to catch, but luckily, his men realized what he was trying to do. Unfortunately, so did Dillinger. He saw the men descending on him and went to pull a gun from his pants pocket. Preferring to fire than be fired upon, Purvis’ men fired off five shots, three of which were direct hits. Dillinger collapsed face-down on the cement and was pronounced dead at hospital 20 minutes later.
Photo from the FBI.

Pretty Boy Floyd

Knowing he was next on the FBI’s checklist, he was trying to lay low in Buffalo, New York, where he and his girlfriend shared an apartment with Adam Richetti, a member of his gang, and his moll. By October, 1934, the rumor is that Floyd wanted to gather up his mother and family in Oklahoma and head for Mexico.

The gang bought a car and headed for Sooner country on October 18, but only made it as far as Ohio before Floyd wrecked the car by skidding it into a telephone pole. The two gangsters armed themselves and prepared to wait outside of town while the women took the mangled vehicle into Wellsville, Ohio, for repairs. Someone reported two suspicious men loitering, and when the police came to investigate the situation, Floyd and Richetti shot at them. A gun battle ensued, and Floyd managed to escape into the woods. He spent days hiding in the woods, living off of berries and fruit, before he managed to scrape up a final meal at a farmhouse. Shortly thereafter, he was discovered.

At least three different stories as to how he was discovered and killed exist, but I’ll give you the FBI’s version first: they had been patrolling the area looking for Floyd and talking to people about any suspicious activity they may have seen when they saw a car inch out from behind a corn crib on a farm. They were headed to question the vehicle when the vehicle crept back behind the crib, apparently deciding that it wasn’t a good time to leave. As the officers approached the car, Floyd jumped out of it with a gun, so they shot at him. “I’m done for, you’ve hit me twice,” he reportedly told them when they closed in on him. He was right – he died 15 minutes later.

At least one other account says that story is total bunk, created to give the FBI all the credit for bringing down the newest Public Enemy Number One. Chester Smith, a retired policeman and skilled sharpshooter, said that he was called in to help them capture Floyd. When Floyd appeared from behind the corn crib, Smith says he shot him twice in the legs, enough to bring him to the ground but not kill him because Melvin Purvis had specifically requested that he wanted to speak with Floyd. Purvis questioned the wounded Floyd, and when he was done, he told agent Herman Hollis to finish the job. Hollis then shot Floyd at point-blank range. So, that’s the story according to Chester Smith, which has been verified by several witnesses. But the FBI never changed their report, so you can choose your own ending.
Photo from PBS.

Baby Face Nelson

After Dillinger died, Baby Face, his wife, and fellow gangster John Paul Chase basically roamed the country freely, going to California, New York and even back to an old hideout in Wisconsin. The FBI finally caught up with him in Barrington, Illinois, not too far from Chicago. The three outlaws were headed through town when Nelson passed a car with plates he recognized. He hated law enforcement so much that he memorized the license plates of certain Feds so he could be sure to take shots at them or vandalize their cars if he saw them.

The plates he spotted on this fateful day happened to belong to FBI agents Thomas McDade and William Ryan, who had spotted Baby Face at the same time he spotted them. Like something out of a cartoon, they both did U-Turns in preparation to give chase and passed each other again. After a few back-and-forth moments like that, it ended up with Nelson, his wife, and Richetti chasing after the Feds. He didn’t know that they had called in backup, though, and soon he was being chased by a car containing agents Herman Hollis and Sam Crowley. When he spotted them, he veered off into a nearby park and stopped, peppering the agents’ car with bullets when they came in right after him. Hollis and Crowley both died. Nelson was also shot – nine times, to be exact – and died at about 7:35 that evening. His body was dumped in the ditch in front of a Catholic church and “someone,” probably Helen Gillis, tipped off the police as to its whereabouts.
Photo from the FBI.

Ma Barker

Nevertheless, the FBI painted a picture of Ma Barker that made it look like she was the ringleader of the notorious Barker-Karpis gang that wasn’t afraid to kill innocent bystanders and had kidnapped the likes of brewery magnate William Hamm and banker Edward Bremer, Jr.

The FBI had been quietly tracking Ma’s letters for months – she and son Fred were holed up in Lake Weir, Florida, and she was keeping in touch with the other three. They traced her to the Lake Weir cottage, where she and Fred died in a flurry of bullets. The FBI says Ma died with a Tommy gun in her hand, but anyone who knew her says that’s preposterous. Some theories say that she killed herself after Freddie died because she was too scared to come out of the house, and the embarrassed FBI spread the rumor that she was just as vicious as the rest of them just to cover their butts. What do you think?
Photo from Biography.

Al Capone

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You already know what a bad dude Al Capone was – he was responsible for the Valentine’s Day Massacre, he illegally smuggled liquor and he was involved in a gang war with Bugs Moran. As his speakeasies got busted by Eliot Ness, Capone decided to (or was convinced to, by some accounts) go to the Eastern State Penitentiary for a while to lay low and avoid drawing attention to himself. It worked – maybe too well.

When he got out and went back to his home base in Chicago, he found that his finances and legal issues were a total mess. The U.S. Treasury Department had been building a tax evasion case against Capone, his brother, and two other gangsters while he was away. He stood trial and on June 16, 1931, pled guilty to tax evasion, telling the judge that he had arranged a deal for a two-and-a-half year sentence only. The presiding judge smirked and informed Capone that he was under no obligation to consider any sort of a prior deal Capone may have made and promptly sentenced him to 11 years in Federal prison. He served seven years, six months and 15 days of that sentence before he was released, his health in severe decline from syphilis he had contracted when he was a much younger man.

Although he took treatment for it immediately after leaving prison, he was never the same again. By 1946, he was reduced to the mentality of a 12-year-old child, according to his doctor, and would rant about Bugs Moran, Communists and immigrants. He had a stroke on January 21, 1947, and died from cardiac arrest four days later.
Photo from PrairieGhosts.

A roundup of a few others:

(image credit: Mike Graham)

See also: 6 Criminals Who Lived Very, Very Well