Al Capone Meets the Cops

Ninety years ago this month, in late August of 1922, Al Capone was involved in the first dust-up big enough to get his name into the Chicago paper. They referred to him as Alfred Caponi (they’d keep calling him “Caponi” for years) in the brief item describing an altercation in which he comes off as a massive douchebag.

Al, it seems, was driving around the loop, drunk out of his mind, and crashed into a parked cab at Randolph and Wabash, injuring the cab driver so badly that he needed hospital attention.

A classier gangster would have run around spreading out cash to keep people quiet, but Capone lacked class in those days. As the Trib put it, “Caponi jumped from his machine, pulled a revolver, flashed a deputy sheriff’s badge and threatened to shoot one of the witnesses, who declared the accident had been Caponi’s fault.”

Capone was arrested and taken to the Central police station, where he threatened to have the arresting officer fired, and told anyone who would listen that he had “pull” that would make life miserable for all of the cops present. “I’ll fix this thing so easy you won’t know how it’s done,” he declared.

Christ, what a douchebag.

Capone was booked on three charges: assault with an automobile, driving while intoxicated, and carrying a concealed weapon. True to his word, he was bailed out and never went to court to deal with any of the charges. At this point in time he was still working for his mentor, John Torrio, who may have been the first gangster ever to say “I own the police” and mean it. You wouldn’t have caught Torrio out driving drunk and waving guns around, though. Capone got better at P.R. later; in 1922 he was just a kid in his early 20s and acting like a frat boy whose daddy is on city council.  He was right, though, about being able to “fix” the thing – the case never went to trial.

The Death of Machine Gun Jack McGurn (and an era)

The imprisonment of Al Capone and the end of prohibition pretty much spelled the end for the gangster era in Chicago (at least for the time being), but there were still scores to be settled.

Capone’s favorite hit mad, Machine Gun McGurn, fell onto hard times and began to receive anonymous valentines in the mail, presumably from gangster who blamed him for the St. Valentine’s Day massacre.

Now, McGurn was a tough character. As part owner of The Green Mill, an uptown speakeasy (still operational, though now fully legal), he talked one entertainer who performed there into staying by cutting his throat in the alley.

But in the mid 30s, with the gang on hard times, the North siders were still angry at him and the south siders were sick of him. Both sides had reasons to want him dead, and, to this day, no one knows WHICH side got him.

But on February 15, 1936, McGurn was bowling at the Avenue Recreation Room, at 805 N. Milwaukee (where the H&R Block is now) when gunmen from some gang or another wandered into the room and shot him to death. At his feet, they left him this valentine:


“You’ve lost your job, you’ve lost your dough
your jewels and cars and handsome houses
but things could still be worse you know…
at least you haven’t lost your trousers!”

Worst. Rhyme. Ever.

The Death of Hymie Weiss: Al Capone’s revenge

With Torrio out of the way, the trio of Weiss, Drucci and Moran made Capone their target and launched one attack after another on him. Capone was repeatedly lucky to escape with his life. Naturally, he fought back.

Weiss, somewhat remarkably, lived for nearly two years after the gang war started before being shot right across the street from Schofield’s Flowers, where Dean had been killed.

Lookouts had been stationed in the next building north of Schofields. Shots fired out the window hit five people and killed 2 of them – including Weiss.

Photo of the building with lines tracing the path of the bullets – the flower shop is visible on the left.

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Diagram of the crime and getaway routes of both the killers AND surviving victims.
The crowd gathers around the body of the other victim: Paddy Murphy.

The cornerstone of Holy Name Cathedral, across the street, was badly damaged in the asault. It’s been fixed up today, except for one hole that is said to be a bullet hole still in place from the hit. People tend to refer to it as the real deal, though commenters disagree, and I find it a bit unlikely myself.

next: the death of Machine Gun McGurn….

The Death of Dean O’Banion

While gangs moved right into the the liquor business as soon as prohibition went into effect, things were fairly quiet for the first few years – the gang’s territories were well carved. But in 1924, things began to go sour. Dean O’Banion, head of the North Side gang, called Johnny Torrio of the south side gang and offered to sell him his business for half a million bucks. Torrio was only too happy – but the deal was a trap. When he showed up to pay O’Banion, cops arrested him. He lost the money, got a jail sentence, and never got the business, which O’Banion happily kept for himself.

But things stayed quiet until November, 1924, when politician Mike Merlo, who had helped keep the peace, died. Two days later, three gunmen including Mike Genna went to Schofield’s Flowers, a State Street flower shop O’Banion co-owned as a day job.

“Hi, boys,” said O’Banion. “You from Mike Merlo’s?”

He shook hands with one of the men – who pulled him forward while another shot him repeatedly.

This was the beginning of the great gang war. Bugs Moran, Hymie Weiss, and Vincent “The Schemer” Drucci took over the norht side and launched an attack on Johnny Torrio – they would have killed him, but when Moran moved in to fire the final shot point blank into Torrio’s head, the gun was out of bullets. Torrio wisely retired, left town, and turned things over to young Al Capone…

next: the death of Hymie Weiss….

The St. Valentine’s Day Massacre

At the beginning of our tours, I often ask if there are any places people especially want to see. The most common request is probably the site of the St. Valentine’s Day Massacre, the spot where 7 gangsters working for Bugs Moran and the North Side gang were lined up and shot, presumably by people working for Al Capone.

Newspaper shot of the scene, with the bodies drawn over so readers didn’t have to see Reinhardt Schwimmer’s brains oozing out over his fallen hat. Schwimmer was not a gangster, but a 29 year old optomotrist who had retired to live off his investments and thought hanging out with gangsters was awesome.

In today’s vernacular, we would say that he wanted to roll with the gangstas, but he was white and nerdy. If you thought he had no brains in his head to hang out with these guys, come on the tour – we have the real picture on the bus.

Questions abound about the massacre – who were the shooters (there’s a new theory every few months)? What was REALLY going on in the SMC Cartage Company, the Clark Street garage where it all went down? Was Moran the target, or was Capone trying to get rid of the north side gunmen who had the irritating habit of trying to shoot him? How many look outs WERE there, exactly (some say they were in one building, though they were probably in every building on the block). And, perhaps most importantly for our purposes, is it haunted, or what?

The SMC Cartage Co on 2/14/1929. The building to the left of it is still standing, but there’s a little field and parking lot where the cartage company used to be now.

As for the hauntings, we hear some stories from the people who live in the senior apartments next door. One old guy who hangs around the site tells us he hears screams all the time. One woman told me she had to hang a dress over her mirror because she kept seeing gangsters in it. But the guy is usually drunk, and the woman’s story seems to be little more than an excuse for her to tell me about judgement day. Other tours make a big deal out of the orbs that are often photographed on the site, but the ghost pictures from there have been pretty thoroughly debunked at this point. So it MAY be haunted, but the ghosts don’t generally have the courtesy to show up on tours. They can easily be FAKED, but that ain’t how we roll, son. We’ll go there, all right (especially if someone asks for it), but we don’t generally spend too much time at the site – we’d rather concentrate on places that seem to have been more active lately.

Quietest of all the ghosts, perhaps, is the infamous Highball the Dog:

Highball was the only survivor of the massacre – one of the more popular ghost stories is that dogs go nuts near the fence. Whatever it was that freaked dogs out there seems to be gone; we’ve heard this enough from people who lived near the site in decades past that we’re willing to believe it, but in recent years we’ve seen dozens of dogs go by the site without incident.

We used to tell the ghost dog story, but not so much now; it’s Lincoln Park, after all, and dogs were walked by the fence during the tour regularly. When they walked by without incident, as they always did, we wound up looking stupid. We’re pretty adamant about not wasting people’s time with complete nonsense on Weird Chicago 🙂

The general theory about the ghost dog is that Highball was so freaked out that, though he didn’t die, he left behind some sort of psychic imprint (or residual energy, if “psychic imprint” is too new agey for you) that dogs picked up on, but that energy/imprint eventually dissipated into the environment. These imprints don’t really last forever – another example of them is the ghostly Lincoln funeral train that used to be seen all over the country, but hasn’t been reported in years, to my knowledge.

But ghosts or none, there are mysteries to be solved. Who were the shooters? Capone’s main hit man, Machine Gun Jack McGurn, was apparently shut up in a hotel room with a blonde showgirl (who he later married) that day. Capone himself was in Florida. One of the more common theories now is that Capone brought in some guys from Missouri to do the job, but it seems unlikely that he would have trusted such a huge job to any but his must trusted men.

Perhaps the best chance we had at finding out died hours after the shooting. Two of the victims lived long enough to answer a few questions. One said “coppers did it;” (this, combined with witnesses saying they saw cops without badges enter the building, leads most people to conclude that the shooters were disguised as cops). The other guy was Francis Gutenberg. One of the cops on the scene knew him slightly (though he later claimed to have been his best friend, and to have been the first guy on the scene) asked him over and over who shot him, but Gutenberg insisted on playing by the rules of the game even up to the end;. Squealing was forbidden.

“Shot me?” he asked. “Why, nobody shot me!”

In any case, the massacre was the beginning of the end for the Capone gang. The scene of carnage shocked people out of thinking of Capone and the gangsters as Robin Hood-type characters. The garage was torn down in the 1960s, and bricks from the North wall were eventually used as a urinal at a 20s-themed restaurant in Canada. The bricks now command pretty high prices on the collectors market, but I would advise against buying them – no so much for the fact that they’re said to be cursed as the fact that if all the bricks SAID to be from the massacre were gathered up, we could probably build the Chicago Spire out of them.

Meanwhile, down in the tunnels

So, in the mid 1920s , the police were hot on the trail of teh Genna brothers (as you know, if you’ve been reading this)> Shortly after the death of Tony, the third to be killed in six weeks, the remaining Gennas wisely went into hiding.

Around this time, a couple of workers in the freight tunnels – the 63 miles of tunnels 40 feet below the loop used to move coal, ashes and other such junk around – reported being attacked by a thug with a blue steel pistol who told them to get lost and get lost fast. Believing it to be another Genna brother (or, more likely, another gangster named Tony Spano who was a Genna ally), 250 cops took the tunnels and made a full sweep, but came up empty handed.

Here’s a newspaper shot of policemen looking for the missing gunman in the tunnels:

The story of gangsters using the tunnels – and every other tunnel in the city – captured the popular imagination. Nowadays, shows on cable like to make it look like the gangsters built the tunnels themselves. They didn’t, but they were certainly a convenient place for them. A gangster could disappear into them and never be found.

The Terrible Gennas Part 3

Very shortly after the lavish funeral of Angelo Genna, the war was back on. It wasn’t long at all before Mike “The Devil” Genna was killed in a shoot-out with the police.

Shortly thereafter, Tony Genna got a call to come to a meeting at a grocery store at Grand and Aberdeen (where the Mark’s Pest Control building is now – easily seen from the interstate). He was shot outside of it by assailants who still aren’t known – by this time, the Gennas had so many enemies that it was anyone’s guess which GANG had had him killed. Vincent Drucci was the initial suspect, but others say Capone had personally ordered the hit.

Tony was given a MUCH quieter funeral than his brothers had – the brothers seemed to be out of money by then. Very small services were held at the De Cola Funeral Home (where Bar Casablana is now near Grand and Racine), and he was transported without ceremony to the family crypt at Mt. Carmel.

Samuzzo “Samoots” Amatuna was a known enemy of the Gennas – but he was actually working for them. He took over the operations of the gang unti a few months later, when he was fatally shot by Vincent Drucci in a barber shop. Capone and the North Siders (Led by Weiss, Drucci and Moran – then just Drucci and Moran when Weiss was killed, and just Moran when Drucci was killed) kept up the war over the Genna’s territory until Capone went to prison.

The Terrible Gennas part 2

So, the Genna Brothers had cleared he way to move into O’Banion’s territory, but they’d also made a LOT of enemies. ALL of the North Siders wanted them dead – and so did Al Capone.

One of them became president of the Unione Siciliane, a major organization that gave him a lot of clout. Capone believed they were just spreading out and biding their time to take over his whole operation. Plus, in retailiation for the death of O’Banion, the unholy trio of Weiss, Drucci and Moran were launching LOTS of hits on HIM – for which he blamed the Gennas.

First to be killed was Angelo Genna. The three north siders chased him down in his car down Ogden Avenue. He crashed into a pole and then shot to death.

His funeral was a MASSIVE affair – by rules of the game, gangsters from all sides paid their respects. He was buried wearing a rich purple robe (which covered the four bullet holes nicely) in a $6000 casket. One gang sent roses, another sent lillies of the valley. Torrio, who was still in jail, sent a huge vase of pink and white carnations. peonies from “Diamond Joe” Esposito, lillies from Al Capone…estimates put the cost of the flowers alone in the hundreds of thousands – much it from Schofield’s Flowers, which had been co-owned by O’Banion.

O’Banion himself had a slightly larger crowd than the 10,000 or so who turned out for Genna’s funeral – but it was a different kind of crowd. “Dean may have had a bigger mob, but a lot of it was curiosity seekers,” said one. “Everyone here was a friend of Angelo.”

He was buried in Mt. Carmel cemetery, very close to O’Banion’s grave, and not far from Mike Merlo’s. One onlooker was quoted as saying “when judgement day comes and them three graves are open, there’s gonna be hell to pay in this cemetery.”

If only he’d known that eventually the cemetery would also contain Weiss and Capone….and a couple more Gennas.

Within six weeks, their reign would be over…