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.

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.

A Forgotten Gang: The Genna Brothers (part 1)

I’ve always had a fascination with the Genna Brothers, an early 20s gang that is nearly forgotten today, though they were known as particularly viscous hoods back in their time. Tony, left, was murdered half a block from my apartment. A couple of them were given funerals on my block, as well.
The Genna Brothers were a refined bunch of gangsters – the kind who had a dozen front row season tickets to the opera. Using loophole in prohibition laws that allowed the manufacture of rubbing alcohol, they paid people all over Little Italy very good money to set up stills in their houses.

In those early days of prohibition, the city was divided into neat lines: The north side was run by, well, the North Siders, led by Dean O’Banion. On the South Side, Johnny Torrio hired some thugs to kill the boss of the area, Big Jim Colosimo, in order to move into the liquor racket. Peace between the two was kept by Mike Merlo, a poltician.

The Gennas were on Torrio’s side, but on the very northern end of it. Having made more liquor than they knew what to do with, they wanted to expand up into O’Banion’s territory, and often told Torrio they’d be only too happy to kill him. Torrio got a taste of O’Banion’s blood after O’Banion double-crossed him in a liqour sale (he told Torrio he wanted out and offered to sell him his business for 500K. He got the money, but the whole thing was a set-up that landed Torrio a short jail term). Two days after Merlo died, a trio led by Mike Genna assassinated O’Banion in his flower shop. The great gang war of the 1920s had begun.

Three of O’Banion’s men (Vincent Drucci, Hymie Weiss, and Bugs Moran, two of whom lived at the Congress Hotel, where Tony Genna also lived in a $100 a night suite) attacked and nearly killed Torrio (after the trio pumped his guts full of lead, Moran fired right at his head point blank – but was out of bullets). Torrio wisely got the hell out of Chicago and turned his operation over to Al Capone, his young lieutenant.

Things were just about to get rough for the Genna brothers…. Three of the brothers would be killed before 1926 was out, and the rest were out of business.

Headlines of the Past

Here are a couple of amusing headlines we’ve run across in our research – the first is from the early 1920s, before the gang war really heated up and the papers still thought of the gangsters as Robin Hood:

And another, from a few years later, when the bootleggers still thought of THEMSELVES as Robin Hood:

We’ve added a bunch of old Tribune headlines to the decorations on our bus, which has been completely updated for 2009!

Al Capone’s House for Sale

There’s hardly an old building in the cit that people don’t say was once owned by Al Capone, Chicago’s own real-live version of Jabba the Hutt. Almost all such stories are nonsense; he kept a rather low profile in the city. But there’s one house that we can all agree that he owned down on the south side – and it’s up for sale!

Capone’s House for Sale

Weird Chicago’s own Troy Taylor is quoted in the article!

The house was featured a while ago on the “Cities of the Underworld’ show, though the episode seemed patently absurd to me – as the show generally does. They go to some great places there, but they rely WAY too much on just relaying the wildest, craziest rumors instead of doing actual research. The woman who showed them around Capone’s house seemed kinda like a phony to me – Capone wasn’t in that house after about 1932, when he went to jail. For her to remember him, and what he was like in the house, she would have to be at least 85 or so. She didn’t LOOK any older than about 60 to me.

The Lincoln Funeral Train in Chicago

For many years, people across the country reported seeing the ghost of the Lincoln funeral train at points where it passed by. This is a good way to illustrate some of the theories that seek to explain ghosts as a scientific phenomenon – in theory, the extreme mental energy exerted by the people watching the funeral go by was so intense as to create a “residual” ghost (a term Troy coined back in the early 90s). So in some cases, people who claim to see ghosts may be seeing a sort of video recording created by intense mental energy. One thing that seems to work in favor of this is that these “residual” ghosts don’t seem to last forever; the Lincoln train sightings seemed to stop around the 1970s.

Similarly, people used to say that a mental “imprint” was left behind by Highball the Dog, the dog who witnessed the St. Valentines Day Massacre, that caused dogs to go crazy when they walked by the site. I’ve heard enough people talk about seeing this that I’m willing to believe it may have been true at one point, but whatever energy dogs were reacting to has dissipated into the environment by now. Ken, Troy and I have seen hundreds of dogs go by that site without incident over the years.

Anyway, the Lincoln funeral train did pass through Chicago on its way to Springfield. After a stop in Michigan City, IN, the train brough it around the lake and to a depot near Michigan and 12th (now Michigan and Roosevelt – incidentally, the Democratic convention had nominated McClennan to run against Lincoln on that spot in 1864). From there, the casket was loaded onto a horse-drawn hearse that led it up Michigan Avenue to Lake street, then down Lake to Clark, and from there to the court house (which was on Clark and Washington at the time) where it lay in state overnight for public viewing. This would have put Lincoln about two blocks from the Tremont House, the hotel where he stayed while in Chicago, and barely a block from the McVicker’s Theatre where John Wilkes Booth was the theatrical hit of 1862. A couple of blocks in the opposite direction was the Republican Wigwam where Lincoln won his party’s nomination in the wild, crazy convention of 1860.

Gangs at the Congress Hotel

Few of the older hotels in town have never had a murder – most of them have played host to at least one. The Drake had the “woman in black” murder that we wrote about here a month or so ago. There was a really grisly stabbing at the Palmer House in the early 70s that remains unsolved.

But the Congress has played host to a really inordinant amount of killings. We find out about more of them all the time – in fact, we’re always finding out strange things about it. One time there was a big party in the Gold Room in which a woman spoke at great length about how apples are evil. Another night in the 1920s something called a “Pagan Ball” was held there. And one time, Jane Addams of Hull House made a speech about Archer Avenue, home of Resurrection Mary, in the haunted Florentine Room – a regular Tic-Tac-Toe of Chicago ghosts!

Today, we’re reading up on how the Congress figures into gangland history. It was not, contrary to what some websites say, ever owned or lived in by Al Capone. Oral tradition has it that he played cards in a room near the Florentine Room, though, and a mysterious phone call made to him in Florida from the Congress Hotel half an hour after the St. Valentine’s Day Massacre shootings led to some arrests in the case. Capone certainly held meetings there, and once even had a guy held prisoner there for awhile, though guarding him was the sort of work he farmed out to others.

Before the gang wars really heated up in the mid 1920s, members of both the north side and south side gangs were living in the hotel at the same time. Vinnie “The Schemer” Drucci and “Greasy Thumb” Guzik have both been named among the residents, and Tony Genna of the The Terrible Genna Brothers was living in a $100 a night suite at the time of his own assassination.

It is not, however (and we’ve made a mistake here ourselves in the past) the hotel where the Dillinger gang was caught in 1933. That Congress Hotel was in Tucson. Chicago papers didn’t always specify this, which led to some confusion.

The most recent gang story there comes from 1993, when leaders of several street gangs held The National Gang Peace Summit a the Congress. It clearly wasn’t THAT successful, but no one was killed or anything. About 300 gang members gathered there, and the hotel was said to be “unfazed” by them.

So gangs have a long history of influence at the place. That one of them fired the a gunshot in or near the Florentine, the ghost of which we may have heard on two separate tours (so far), is hardly impossible.