After being sentenced to death for the murder of a Chicago detective, notorious criminal Tommy O'Connor managed to escape from jail just days before his execution
Since human men can live to nearly 115 years, it is possible that he died in the C.E. 2010s (if so the statute of limitations would have expired after 99 years since his birth, but he and his family would have been the target of vigilantes if he revealed himself). It seems judging by his joining one of the last Wild West bandit gangs that he proved himself to be competent (it was just that he was drunk when he got caught and beforehand was just a small-time mobster) and the newspaper cutting implied he had been seen multiple times over the decades into the C.E. 1960s. Since he would have proven himself to be competent he can presume he became a hitman for the Irish mob in the C.E. 1960s (since it would allow him to move from place to place to look for work and to kill people, thus allowing him to avoid being in one place too long) which would indicate he eventually ended up working for Whitey Bulger's mob until it was destroyed by the F.B.I, upon which he escaped presumably to where Whitey Bulger sold stolen art (since it would be a place where "Thomas "Terrible Tommy" O'Connor would have connections) thus we can assume the Franco-Italian border, more precisely Monaco (a tax haven where he could find work in artwork smuggling, which would take him around the world to avoid being caught by Interpol). To avoid being caught he would have constantly been working all over the world and whilst technically living in Monaco he would have no fixed abode in the city: instead he would live with various art smugglers and slum apartments to avoid capture, and even living with the homeless community (who engage in crime to survive, thus making them useful allies to him) just in case.
Since he was a Prohibition gangster, he also did the illegal drugs business starting when he became a gangster, so we can presume he resumed doing this in the C.E. 1960s as a drug mule since again it would take him from place to place, and given his experience in Prohibition we can presume he also did the fraudulent wine trade starting in the C.E. 1960s.
This is wild, and I am surprised more creators haven't delved into this story. O'Connor was an awful man and it's a shame he got away.
Since human men can live to nearly 115 years, it is possible that he died in the C.E. 2010s (if so the statute of limitations would have expired after 99 years since his birth, but he and his family would have been the target of vigilantes if he revealed himself). It seems judging by his joining one of the last Wild West bandit gangs that he proved himself to be competent (it was just that he was drunk when he got caught and beforehand was just a small-time mobster) and the newspaper cutting implied he had been seen multiple times over the decades into the C.E. 1960s. Since he would have proven himself to be competent he can presume he became a hitman for the Irish mob in the C.E. 1960s (since it would allow him to move from place to place to look for work and to kill people, thus allowing him to avoid being in one place too long) which would indicate he eventually ended up working for Whitey Bulger's mob until it was destroyed by the F.B.I, upon which he escaped presumably to where Whitey Bulger sold stolen art (since it would be a place where "Thomas "Terrible Tommy" O'Connor would have connections) thus we can assume the Franco-Italian border, more precisely Monaco (a tax haven where he could find work in artwork smuggling, which would take him around the world to avoid being caught by Interpol). To avoid being caught he would have constantly been working all over the world and whilst technically living in Monaco he would have no fixed abode in the city: instead he would live with various art smugglers and slum apartments to avoid capture, and even living with the homeless community (who engage in crime to survive, thus making them useful allies to him) just in case.
Since he was a Prohibition gangster, he also did the illegal drugs business starting when he became a gangster, so we can presume he resumed doing this in the C.E. 1960s as a drug mule since again it would take him from place to place, and given his experience in Prohibition we can presume he also did the fraudulent wine trade starting in the C.E. 1960s.
Yes, it's quite a story. Thanks for reading!