Jelly Roll Hogan: Eureka’s Most Notorious Gangster

Italian gangs, more specifically the Mafia, get all the underworld glory. So do the cities of New York and Chicago. Who hasn’t heard of Don Vito Corleone, or Al Capone? Of the Gambinos or the rat-a-tat-tat of a machine gun shot from a car hurtling down, fittingly, Wacker Drive? Or the St. Valentine’s Day Massacre?

But did you know that the famous massacre on Cupid’s day was, purportedly the Italian response to territory encroachment in Chicago by the St. Louis-based Egan’s Rats? Did you know that St. Louis had a ferocious history in gang violence, rivaling that of cities much larger? And did you know that one of those gangsters not only had a home in the city, but built a mansion near Eureka?

The Irish Mob is the oldest organized gang in U.S. history, reaching back a hundred years or more before they had any real competition from Italian or Jewish gangs formed in the late 1800s. Remember “The Gangs of New York” and Leonardo DiCaprio’s dodgy Irish accent? (Sure, and he was a right eejit, as useless as a chocolate tea kettle, he was!)

Well, St. Louis was a hotbed of organized gang activity, especially during that failed moral experiment called Prohibition. And a key character was one Edward J. Hogan, Jr., or Jelly Roll Hogan, though I wouldn’t go calling him that because he didn’t like the moniker and was a persnickety type that once beat up a man on the Missouri Capitol steps in broad daylight. Why was Jelly Roll Hogan on the Missouri Capitol steps in broad daylight? Well, he was a multi-term Missouri State Representative and Senator as well!


Jellyroll Hogan 1

Mr. Hogan (hey, I ain’t calling him that other name…I mean, he’s dead, but why take chances?), the son of a St. Louis police chief, went into saloon keeping, as you do if you’re the son of a police chief. But, with the passage of the 18th Amendment and only 1,500 nationwide agents to enforce it, well, what is a poor boy to do? Hogan and some of his ne’er-do-well buddies started running beer and liquor. And they found, as did like-minded peers in most major cities, the passage of something called an “Amendment to the Constitution” did little to quench the thirst of the people and so their scale of bootlegging increased mightily.

Hogan, born in 1886, was involved early in St. Louis city politics and was elected to the state legislature, as a Representative, in 1916. He left that post in the spring of 1920, taking the Prohibition years off for escapades slightly more profitable and slightly more illegal. Running his gang and enterprises from his headquarters at Jefferson and Cass Streets in the city, Hogan got himself named as Deputy Inspector for the State Beverage Department of Missouri, also in 1920. In that capacity, Hogan’s duty was to be sure that all beverages produced in Missouri were of the non-alcoholic variety and were produced safely and legally.

Uh huh.

So, just hypothetically, if someone was making soda pop in St. Louis, and that someone had a bit of cash to slip under the table and Mr. Hogan was, hypothetically, on the other side of that table, then inspections of said soda pop factory might be delayed. Who knows what might have been bottled during the delay? (We all do.)

All well and good, right?


Gangsters are greedy. You’ve seen the movies!

Hogan, though identified as an Irish gangster, was ahead of his time in that he embraced thugs from many ethnicities. (Well, I’m not sure he embraced them, you know, per se, because, enlightened as he was, that kind of thing was frowned upon.) Hogan’s Gang included Humbert Costello, Charles Mercurio, Leo Casey, Abe Goldfeder, John “Kink” Connell, and Patrick Scanlon.



Jellyroll Hogan 3


But his gang did most decidedly not include William Egan. In fact, Egan’s Rats, from the St. Valentine’s Day Massacre mentioned before, were his bitter enemies. Not content on dividing up the riches of St. Louis and surrounding counties, Hogan and Egan entered into one of the most deadly, bloody turf wars of the Roaring Twenties right here on the streets of our fair city.

The Hogan-Egan war reached its peak during the years 1921-23 and seemed to be started by an Egan employee, Max Greenberg, who took umbrage at being the target of an Egan assassination attempt over a stolen whiskey shipment. Greenberg joined the Hogan gang and paid three members of his new gang $10,000 each to kill Willie Egan in front of his saloon, located at Fourteenth and Franklin on Halloween night, 1921. Egan’s buddy, “Dint” Colbeck, reached Egan’s side just in time to see the action and fingered the three assassins as James Hogan (brother), Luke Kennedy and John Doyle.

Well, that did it.

For the next two years, both sides took every opportunity to hurl bullets (and cars and who knows what else) at each other, not caring much for where said bullets were hurled, or whom might be standing around, all innocent like. Accounts too numerous for this article abound and, for further research and jaw dropping, I recommend the book “The Gangs of St. Louis: Men of Respect,” by Daniel Waugh. However, here are a few just to whet your appetite.

On December 30, 1921, a carload of Egan shooters opened fire on several Hogan men as they left the police station in downtown St. Louis. Luke Kennedy was severely wounded in the leg and Hogan Gang attorney, Jacob Mackler, had his derby removed via shotgun blast, though he was, miraculously not hurt. A week later, in the dawn of 1922, one of Willie Egan’s fingered killers, John Doyle, was shot and killed in a high-speed chase with St. Louis police. In April of that year, Kennedy, still nursing his leg, was cornered and, according to a witness, taunted and then killed by Egan gunmen.

Retaliation came from Hogan by shooting up Dint Colbeck’s plumbing store. Egan gunmen countered the next day with a drive-by shooting of the Boss Hogan’s home at 3035 Cass Avenue, where Hogan’s parents were staying and they spent some time diving for cover. The open gang war was disturbing some, including Monsignor Timothy Dempsey, who met with the gang members individually and persuaded a truce. Of sorts.

Max Greenberg, one of the catalysts of the war, was placed on a train to New York. But the treaty left the Egan Gang with the lion’s share of power and they were not ones to be good winners. The dominant gang antagonized at every opportunity.

It has not been mentioned that, in addition to bootlegging and basically having a license to print money, the greedy gangs also dabbled in bank robbing.  After an Egan bank job, Egan gangster Chippy Robinson called the police to pin the robbery on the Hogan Gang. Hogan himself, and some of his men, were arrested for the deed but the charges failed to stick.

On September 2, 1922, Dint Colbeck (he sure got around), and three of his men, ran across Hogan men Abe Goldfeder and Max Gordon and chased them down Locust Street in a hail of gunfire, Gordon losing an eye in the exchange. But it wasn’t until February 1923 that the war again reached a fever pitch.

Jacob Mackler, he of shot-off derby fame, was shot and killed by Colbeck and his men in Old North St. Louis on February 21 and the city erupted once again. Hogan’s Cass Avenue home was again shot up in March and after that Hogan and an associate traded shots with a carload of Egans while traveling at a high rate of speed up North Grand, Egan’s car eventually striking and critically injuring a 12 year old boy.

The city had enough and Monsignor Timothy Dempsey, along with police officials and the press, sought a truce once and for all. Both Colbeck and Hogan wrote letters to the city stating that the Egan-Hogan war was over and that peace would reign.

After all of this, after the charges for bank robbery, after the known bootlegging, after the violence and infamous notoriety in a city caught in a web of terror, Edward Hogan returned to the legislature. Hogan served as a Missouri state representative from 1934-1940 and then as a Missouri state senator from 1944-1956.

Jellyroll Hogan 2

If someone wants to make an observation about the parallel of Hogan’s two lives, here would be the place.

Hogan, in his quieter years, built a mansion on 140 acres of land in Jefferson County, on the outskirts of Eureka. That home and its barn, currently being converted into a rentable party space and owned by Brookdale Farms, was built in 1933 and served as a place of refuge for Hogan. This home, shown in accompanying photographs, stands in stark contrast to a time and a place not as gentle and quiet.

Edward “Jelly Roll” Hogan was given a gift not extended to his peers, like Al Capone and Bugs Malone and Willie Egan: he lived past his wild days. And he was an example contrary to F. Scott Fitzgerald’s assertion that “There are no second acts in American lives.”


2 thoughts on “Jelly Roll Hogan: Eureka’s Most Notorious Gangster”

  1. Jellyroll was my GG Grandfather. The article is one of the few to tell both sides and get most of the facts right.
    Good read. Thanks.


    1. Thanks for the shout out, we really enjoyed doing this article and it got a huge response. Apparently, there is much interest in your GG Grandfather.


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