The Chicago Outfit has had its hands in some of the most controversial political shootings and events in history, including, allegedly, the assassination of President John F. Kennedy in November 1963. But one “assassination” that is rarely discussed is that of Chicago Mayor Anton Cermak thirty years earlier, in February 1933, while he was attending an event in Florida with then President-elect Franklin D. Roosevelt.
There has been much speculation over the years about who was really behind the murder and whether or not the target truly was FDR. And while, many believe the “case is closed,” as we know from history, cases like these are never “truly” closed.
Our Chicago historian, Dushan (Toodoped) Dzonov takes us down Conspiracy Lane in this insightful dive into this largely forgotten “assassinaton.”
In this article, I want to discuss one quite old “situation” that occurred back in 1933. At this point, I can’t quite call it a possible “mob hit,” but this “situation” is quite similar to many other “situations” that occurred during the following decades.
There is not much difference between high-profile public killings such as the assassination of President Jack Kennedy or the public “hit” on infamous Mafia boss Joe Colombo. Or even the killing of JFK’s brother, Robert Kennedy, which was also executed (no pun intended) in the same style and also occurred in front of more than a few witnesses.

In fact, some of these killings occurred in front of thousands of eyewitnesses, and, in most cases, the alleged assassins were also killed, sooner or later. On top of that, all these cases remain “closed,” but, at the same time, there are still many unexplained details or connections regarding the murders, mainly because the assassins had minimal and almost non-existent mob connections.
All of the previously mentioned targets were killed by some type of “strange” and lone gunman, who, in some way, sacrificed their lives in publicly eliminating a high-profile individual, allegedly for their own or personal ideas and reasons. This wasn’t happening only in the U.S., but also was, and still is, happening all over the world. For example, Colombian drug lord Pablo Escobar also used similar tactics when eliminating public figures, Mexico’s AFO cartel, or even today’s suicidal Islamic extremists who sacrifice their own lives in the blink of an eye just to eliminate their prime targets.
Obviously, these types of killings sometimes were triggered by one single mind who decided to solve the problem in his own way, but some were triggered by a group of people who decided to use some lunatic with crazy ideology and with some social problems, ready to sacrifice his freedom and life.
I personally believe that all examples were mainly accomplished with the help of “Machiavellian” manipulation, followed by massive corruption. Once that happens, it is very hard, almost impossible, to make one overall conclusion about who did what and whether or not there was someone else behind the murder or whether the assassin acted alone.
Well, there was one alleged assassination attempt that preceded all of the previously mentioned situations, and in this case, the alleged target was a U.S. President. Luckily for him, he survived that attempt, but one famous (or infamous) Mayor, who was also present at the time, got a bullet in his stomach and later died. Since this was a tragedy that occurred decades before the JFK and Colombo assassinations, my personal belief is that there is some similarity in the details of the killings between this one and the rest.
The high-profile killing of which I’m speaking involved President-elect Franklin D. Roosevelt and the alleged “unlucky” mayor of Chicago, Anton Cermak. The events happened in 1933 at Bayfront Park in Miami, Florida in front of hundreds of visitors who came to see their President. And it all ended with the fatal stomach wound of Chicago’s Mayor Cermak.
If we want to solve the case, first, we have to look at the four main individuals involved in the “situation” one by one: President-elect Roosevelt, Mayor Cermak, one high-level Mafia boss, and the alleged assassin.