Adam Selzer

Chicago mobsters of the 1920s have become a sort of "Pirates of the Caribbean" for our city. There are gangster tours, a Tommy Gun's dinner theater, speakeasies that are no longer speakeasies, and we once had a sports team called the Chicago Hitmen. So it's easy to gloss over the fact that these murderous lawbreakers introduced the world to concepts like the drive-by shooting. The Prohibition-era criminal is romanticized in gangster movies and pop music. And, yeah, some of them in hindsight seem particularly silly and curious, despite being evil, with their goofy hats and names like "Willie Potatoes" and "Cockeyed Louie." The Irish North Side Gang and South Side Italian Chicago Outfit waged bloody war on what is now our doorsteps and doughnut shops. Here, we rank the 17 most notorious killers, thieves, bootleggers and, yes, politicians that continue to fascinate us.RECOMMENDED: The 50 best gangster movies of all time

RECOMMENDED: Our complete guide to Halloween in Chicago Employees of the old jail on Illinois and Dearborn were tough to scare. Stories of the jail being haunted circulated from time to time, and an old parade of serial killers and multi-murderers were held there over the years. But there was one guy who really gave the jailers the creeps: Sam Cardinella, a gang leader who had been known around the South Side as "Il Diavolo"—The Devil. Cardinella seems like a guy who read Oliver Twist as a how-to manual. He ran a pool hall on 22nd Place where he'd lure boys, initiate them into his gang, then send them out on robbery jobs, from which he'd take most of the money. One of the kids, Nicholas Viana, walked into the pool hall one afternoon on the way home from choir practice and committed his first of his several murders only days later. Viana cursed Cardinella just before he was hanged on his 19th birthday. Vianna's body was placed in a wire basket and driven away in an ambulance instead of a hearse. Jailers thought it was weird, but shrugged and got on with their jobs. Months later, Cardinella himself was brought before the noose, after months of pacing in his cell, refusing food and scaring the heck out of the guards. The night before his hanging, it's said that he was uttering the name "Viana" repeatedly as he had his final meeting with his family. On the scaffold, though, he lost his nerve completely. He collapsed, and had to be hanged while tied to a chair. His body, too, was

You can say what you will about the presumptive GOP nominee, but his Adrian Smith-designed tower is a masterpiece of architecture, managing to fit in perfectly between Van der Rohe's IBM tower and the Wrigley Building, despite being exponentially larger than either. To fit in so well between black and white buildings is quite a feat. Of course, now that the owner's name is there in giant letters, the building has become a popular site at which to take selfies with one's middle finger exposed. In the shadow of the building sits Taft's statue of George Washington, with a base quoting our first president as saying that our government will "give to bigotry no sanction, to persecution no assistance."  Buried in the archives of the Tribune is an interesting bit about the next-door neighbor, the Wrigley Building, with its lovely clock tower and gleaming white terra cotta facade. When it was built in 1920, it had the whole of Michigan Avenue above the river to itself—it was an area populated by bohemian dives and gas stations. Its construction was the beginning of the Magnificent Mile.  On April 4, 1920, the Tribune published an article praising Mr. Wrigley for not putting his name on the building in giant letters. Even though it would be "the most commanding site" in the midwest for an advertisement, like the ones for which Mr. Wrigley was paying a fortune in New York, it would only feature a small brass plaque that said "Wrigley Building." Nothing more. "Mr. Wrigley's modesty and r

One of the most durable urban myths of Chicago architecture is that turn-of-the-century utilities mogul Sam Insull designed the Civic Opera House to look like an armchair with its back facing east—so that if he were sitting in it, he'd be turning his back on New York. The whole opera house, the story goes, was built after his wife was rejected by the New York Opera companies. A cursory glance at the facts would show that the story has no basis. In fact, Mrs. Insull was about 60 when the Civic Opera was built, and she was never an opera singer. However, before their marriage, she had been a professional actress, and staged a small comeback in 1925. Most reviews of her were rather polite, but screenwriter Herman Mankiewicz later said that he passed out drunk trying to write a scathing review for the New York Times, a scene he then wrote into Orson Welles' classic film Citizen Kane after Kane builds an opera house for his new wife, Susan Alexander. It's generally agreed that the character of Susan Alexander is mostly based on Marion Davies, William Randolph Hearst's girlfriend, and her film career. But Welles did say that Insull was part of the inspiration for Kane, too. And after Mrs. Insull's New York stint, Insull did lease the Studebaker Theater so she could start a repertory theater there. Work on the Civic Opera started right around the time that repertory project failed. There's more to the story on Mysterious Chicago Interested in blogging for Time Out? Contact us here

Kate Kane was the second woman to be accepted to the bar in Wisconsin, and then the 13th in Illinois, and she's largely forgotten now. But as perhaps the only female lawyer in practice in Chicago for much of her career, she was famous in her day for defending the high profile “trunk murderers” in 1885. Early in her career, she made national news when, tiring of a judge’s sexist comments, she threw water in his face. Outbursts like this would become something of a trademark of Kane's. She was frequently written up in the press, both locally and nationally, and a great many of the article s were about her hitting people with parasols, her shoes and, in some cases, with her fists. When she took her daughter to work (as she often did) and someone stepped on the young girl’s foot, Kate took it as an intentional assault and clobbered the guy. Some of her comments recorded in the press over the years aren’t exactly 21st century-friendly (to put it mildly), but it’s possible to be a pioneer and still be a product of your time (or even to be a pioneer and sort of a jerk). Either way, Kane deserves to be remembered for the trails that she blazed in Chicago. You can read more on Kane at the Mysterious Chicago blog. Recommended feature See the best things to do this week in Chicago

The press called her "Chicago's Woman Sherlock Holmes." Her publisher called her "The Mistress of Mysteries." It's a shame, really, that there isn't a chapter on Mary E. Holland in every anthology of Chicago history stories. Hers is one of those fantastic stories that fell through the cracks before anyone could really learn enough about her. Mary was the assistant editor of Detective, a magazine for police officers, and did a lot of investigative work herself. She studied fingerprint sciences at Scotland Yard, then helped train law enforcement agencies in the United States, using dusting powders she invented herself. In 1910, she was one of the experts called to the stand in the first modern trial where a murderer was convicted based on prints. Only bits and pieces of her work have come to light, most notably her notes on the "Bate Murder"—the first case in which a person was killed in a car. Billy Bate was found slumped over the steering wheel of a 1904 touring car; the man who hired it, "Mr. Dove," was gone without a trace. She examined the automobile and wrote up her notes for a Chicago paper. “There exists in the blood stains on the automobile the unmistakable evidence that some person or some heavy object has been dragged from the rear seat over the right side of the machine,” she wrote. “This was done when the blood was warm. I cannot be mistaken in this. The hands of the person, whose finger prints still remain on the front portion of the machine and on the brass of th

H.H. Holmes was recently in the news again, as reports circulated that Scorsese and DiCaprio will soon bring The Devil in the White City to the big screen. But the news has a few local historians cringing: Devil in the White City is a gripping book, but it's more of a novel than a work of nonfiction. If you read the endnotes, Erik Larson is very upfront about how much of the stuff about H.H. Holmes simply came out of his imagination. Indeed, many of the stories that have become common about Holmes are based more on tabloids and pulps than on primary sources. Holmes is certainly known to have killed a number of people, but the 27 he confessed to were probably an exaggeration (a few of the people were still alive). The idea that he killed hundreds of people was first mentioned in a couple of 1930s pulps and wasn't taken seriously at the time. His famous "murder castle" (which was often just called The Holmes Castle until the 1930s) did indeed have a number of secret rooms and secret passages, but the city knew all about them before the World's Fair even opened. In March 1893, there was a large article about them in the Tribune after Holmes was caught using hidden rooms to hide furniture he'd bought on credit and never paid for. Stories of medieval torture equipment in the basement come mainly from a game of "telephone." For about a week in 1895, when investigators were tearing the building up, papers would announce that he'd been hanging victims because they found a rope, that

It’s no secret that Chicago is home to dozens of places that are said to be haunted, and we have plenty of haunted tours to back those up. Whether the ghosts are real in any of these spots is above my pay grade, but I’ve spent years researching the history at these locations, as well as tracking down firsthand accounts of ghost sightings. Some places, like Bachelor’s Grove Cemetery and the former Excalibur Club, are fairly well-known for their ghost lore (despite the fact that the backstories don’t always check out), but here are a few lesser-known haunts around the city. Macy's  The former Marshall Field’s location is said to have served as a morgue after the deadly 1903 fire at the nearby Iroquois Theater. It was more of a hospital, really, but many victims died there. An employee recently told me some of her co-workers didn’t like to go to one particular floor because they sometimes saw apparitions like ominous coffins. Fine Arts Building  A grim backstory on this building is hard to come by (unless you count the fact that H.H. Holmes’s daughter Lucy had a wedding here in the 1920s), but several people have told me they've seen people dressed in “old-fashioned” clothes who appear and disappear before their very eyes.  Bethania Cemetery Overshadowed in ghostlore by the nearby Resurrection Cemetery, this graveyard in Justice is said to be home to the ghost of an elderly woman who appears by the gates and cusses people out. This is the kind of ghost every Chicagoan shoul

Some Chicago history stories come out of the archives and make you marvel at the fact that the tale hasn't been retold 100 times to you by now. Today, Mysterious Chicago is telling one of those: the legend of Conway, the "One-Legged Killer Clown" of 1912. Charles Cramer, alias Charles Kramer or Charles Conway, was an itinerant circus performer in the early 20th century. He and his wife took up with a vacationing couple in 1912, one of whom was an heiress. When the heiress was found strangled to death in a rooming house, the Cramers vanished, and a nationwide dragnet was launched as police searched for Mr. Cramer, whose main identifying characteristic was a peg leg (he'd lost one leg below the knee in an accident and declined to get a proper prosthetic). When captured, Cramer is said to have joked with the jailed. "Did you know you can't hang a man with a wooden leg?" he asked. "You have to use a rope!" Though a first-degree murder charge had sent plenty of men to the gallows, Cramer was given a life sentence in Joliet. The wooden foot didn't seem to slow him down: He escaped from jail in 1925 and doesn't seem to have ever been found. He'd be about 130 today, so it's assumed he's dead, but how long was a killer clown walking free, perhaps making a living hidden in plain site in some two-bit circus? .  

With all the uproar this week over a Minnesota man killing a famous Lion in Zimbabwe, one can't help but think that (for better or worse) there was no scandal whatsoever when a lion was "hunted" and killed in Chicago in 1909. In that year, Col. Theodore Roosevelt left the White House and went on safari in Africa. Though Selig Polyscope, a Chicago-based film company, tried to make a deal to film the excursion, they wound up having to settle for filming a reenactment (which plenty of viewers mistakenly believed was the real deal, a misconception Mr. Selig did nothing to discourage). A lion bred in captivity was brought into a jungle created in the Selig studio at Byron and Claremont, where, having been bred in captivity, it seemed scared and confused. Toward the end of filming the $15,000 movie, the lion was shot and killed before the camera.  The movie, like almost all Selig Polyscope films, is now lost, though by all accounts it featured a lot of hand-shaking and a lot of Roosevelt saying "dee-lighted." Being a very different time, the fact that an animal had certainly been harmed in the making of the motion picture doesn't seem to have caused much of a stir. More info on the shoot is at the Mysterious Chicago blog.      

Elections get ugly. It's the nature of the game. But nothing going on this year quite compares to what happened in 1893. With an election approaching right around the time that the World's Fair opened, one paper claimed that if Carter Harrison were elected, every criminal in the country would move to Chicago.  Simply calling Carter Harrison "soft on crime" was not enough for the Chicago Evening Journal. In March 1893, it published an article entitled "THIEVES ON THE RUN: Thugs Flocking to Chicago From Every Quarter." The Journal insisted that "dangerous and desperate men, familiar with vice and crime in every form" had been flocking to the city ever since Harrison was nominated. "When a town or city is labeled 'right,'" it wrote, "murderers, thieves, pick-pockets and all species of criminals inquire no further...for a month past, every train that entered Chicago has brought recruits to the criminal population...'On to Chicago' is the cry of the criminal army, and on to Chicago that army is marching. Part of it is here already, and if Carter Harrison should be elected Mayor the city will be given over to plunder." It went on to estimate that 200 new professional criminals, encouraged by Harrison's chances, were arriving in town every day. "The very life of the city hangs on the result of next week's election," they roared. "Harrison must be defeated." Of course, Harrison was not defeated. And a check through the paper's archives indicates it managed to refrain from saying "we

RECOMMENDED: The 17 most notorious gangsters from Chicago After Sam "Il Diavolo" Cardinella was hanged in 1921, jail officials found his friends in an ambulance behind the jail, trying to bring his body back to life. He had taken steps to insure that he would choke, not break his neck, and the prison physician felt that if they'd hadn't been caught, there was a slim chance that they might have pulled it off. Such business wasn't necessarily unheard of; in 1882 doctors in Chicago had had a little success in trying to shock a hanged murderer back to life, Frankenstein-style. And the reason Cardinella thought it would work was said to be that they'd already tested it—successfully—on one of his underlings, Nicholas "The Choir Singer" Viana, who had been hanged on his 19th birthday four months earlier. Prison lore held that "magicians" had stood around Viana's body at a nearby undertaking parlor, chanting in Sicilian while doctors worked on the body, until Viana began to breathe and moan. Some said that was as far as they managed to get, some said they stopped there deliberately and let him die as a traitor to the gang, and a few even claimed that Viana was now alive and well in hiding on the west side.  This tale of surviving the noose has always seemed like an urban legend, but some articles found in June 1921 editions of the Chicago Herald Examiner, Chicago Daily News, Chicago Evening American and Chicago Evening Post on microfilm show that prison officials took the story very,

There are plaques around town dedicated to William Hale Thompson, a former mayor of Chicago. You really think that even in Chicago, where our political crooks are almost a point of pride, we would have scrubbed away all references to old Big Bill Thompson, our gangland-era mayor.  Big Bill served two terms in the 1910s, later pretending to go on an expedition or fishing in South America in order to keep his name in the news. When he came back to run for mayor again in 1926, he put on one of the most bizarre political stunts in Chicago history: debating with rats. After a few candidates for local office spoke in the Cort Theatre on April 6, 1926, Thompson came onstage with two caged rats from the stockyards, one named Doc (for Doctor John Dill Robertson, one of his political opponents) and one named Fred (for Fred Lundin, another opponent). As to which was which, Thompson pointed to one and said, "This is Doc. I can tell because he hasn't had a bath in 20 years." Then, after lambasting the two rats for a while, he went into one of his rants against the King of England. The man had been the mayor twice, and went on to win the election to serve a third term, and seems to have thought of himself as a serious candidate to be the Republican nominee for president in 1928. When he ran again in 1931, though, it's said that the five measly districts he managed to win only went to him because they were run by gangsters (who adored Thompson).  When he was trounced in the 1931 election, t