If you’ve read and watched Why Was Saint Paul a Good Place for Bad Guys, then you already know that not everyone wore a halo in the saintly city. According to Paul Maccabee, author of John Dillinger Slept Here, the “O’Connor System” was the name for the arrangement between “Saint Paul’s Finest” and the most notorious mobsters and villains of the 1920s and ’30s. A bribe to the Saint Paul Police Department upon arrival bought you protection from arrest and harassment, so long as you didn’t harm one hair on the head of any person in the city limits of Saint Paul. And, astonishingly, the system worked. Until it didn’t work.

Why would the upright citizens of this fair city allow such a thing to go on? What possible upside could there be in having notorious gangsters walking our streets, frequenting our establishments, living in the house or apartment next door? In a word, access.

One must remember the times. This is the era of Prohibition. The everyday citizens of Saint Paul had no access to the fun stuff but through enterprising crooks willing to risk it all for a buck. Who else would carve a speakeasy out of that vacant apartment down the street? Who else would host lavish parties where booze flowed freely? Who else would set up illegal gambling casinos hidden in plain sight along Saint Paul’s Mississippi River Boulevard? And quite important to society people: Who else would be so brazen as to personally deliver illegal alcohol for your daughter’s wedding reception in broad daylight to The Hotel Saint Paul, right in the the heart of downtown? Yep, you got it. You’re catching on.

Clearly, these two seemingly separate layers of society – upstanding citizens and their criminal counterparts – were, in fact, in constant interaction, each using – and being used by – the other. All under the helpful auspices of the Saint Paul Police Department. Well, as stated above, the system worked, until it didn’t work. So where’d it all go wrong?

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Step inside Neumann’s Bar: MN’s oldest, continually active watering hole. Opening its doors in 1887, the bar became one of the notorious speakeasies of the 1920s – and let’s just say that gangsters found their way inside.

Minnesota is no stranger to notoriety when it comes to crime and criminals. In June 1977, the wealthy heiress Elizabeth Congdon and her nurse were murdered inside Glensheen Mansion on the North Shore. Congdon’s adopted daughter, Marjorie, and Marjorie’s then-husband were accused of the crime. But the fallout from the trial and subsequent suspicions for other crimes is the stuff of legend. Read all about it in Glensheen’s Gilded and Grisly Past.

Ever wondered which building in downtown Saint Paul holds the distinction of being the city’s oldest? Find out in this episode of 30-Second Minnesota.