Adelard Cunin, better known as George “Bugs” Moran, was a Chicago Prohibition-era gangster. He was incarcerated three times before turning 21. On February 14, 1929, in an event that has become known as the Saint Valentine’s Day Massacre, seven members of his gang were gunned down in a warehouse, supposedly on the orders of Moran’s rival Al Capone. Take a look below for 25 more twisted and interesting facts about George Moran.

1. Moran was born Adelard Cunin to Jules and Marie Diana Gobeil Cunin, French immigrants, in Saint Paul, Minnesota.

2. While attending Cretin, a private Catholic high school in Saint Paul, he joined a local juvenile gang.

3. Moran left school at the age of 18 and was later caught robbing a store.

4. He was then sent to the state juvenile correctional facility. Bugs was put in jail about three times before he turned 21.

5. Moran escaped and fled to Chicago, Illinois, where he was later caught trying to rob a warehouse, taking part in a horse-stealing ring, taking part in a robbery involving the death of a police officer, and robbing a freight car, for which he received a variety of prison and jail sentences.

6. He married twice during his career as a gangster, the first divorce stemming from his wife’s disapproval of his lifestyle.

7. The bootlegging operation of Hymie Weiss and Bugs Moran posed a significant challenge to Capone’s South Side Gang.

8. Moran and Capone then led a turf war with each other that cost them both.

9. Moran’s hatred of Capone was apparent even to the public. Moran was disgusted that Capone engaged in prostitution.

10. He would not increase profits himself by engaging in prostitution rings because of his Catholic religion.

11. Torrio’s gang killed Dean O’Banion, and in an attempt to avenge him, Moran and Weiss made an attempt on Torrio’s life.

12. Later, they went on to make a failed attempt on Capone’s life at his headquarters, the Hawthorne Inn in Cicero, Illinois.

13. More than one thousand shots were fired at the inn and at a nearby restaurant in their attempts to kill Capone.

14. In retaliation, Weiss’s life was taken by Capone’s gang, and Moran became head man of the North Side Gang.

15. Responding to Weiss’s death, Moran tried to kill a member of Capone’s gang, resulting in an attack, allegedly from Capone, known as the St. Valentine’s Day Massacre.

16. On February 14, 1929, Capone probably tried to strike a decisive blow against Moran with the notorious Saint Valentine’s Day Massacre.

17. After the St. Valentine’s Day Massacre, Moran laid low and tried to consolidate his empire.

18. After Prohibition, the mafia’s business was on its knees. The North Side Gang lost its influence and Moran had to go back to his earlier life of small time crime like robbery, extortion and fraud.

19. Moran’s escapades came to an end in April 30, 1939, when he was arrested for conspiring to make $62,000 worth of American Express checks.

20. He was freed on bond and escaped, but was later captured in December 21, 1943.

21. By the mid 1940s, he was broke and had to involve himself in robberies, which got him a 20 year jail term after an unsuccessful robbery in Dayton, Ohio.

22. After serving his sentence, he was once again tried for robbery and sentenced to 10 more years in 1957.

23. Moran died on February 25, 1957, at the age of 63, just months in to the second sentence at Leavenworth Federal Penitentiary.

24. It’s believed that he died from lung cancer.

25. Even though Moran was once a rich mafia boss, he died a poor man with just over $100 under his name.