The Premise
Fact: Al Capone’s Chicago Outfit gang was a strong presence in Chicago in the 1920s, supplying illicit liquor, bribing public officials, and protecting their interests with violence.
Fact: The St. Valentine’s Day massacre was a real event, carried out by Al Capone’s gang. While there was no official tie of Mayor Bill Thompson to the massacre, many felt like he turned a blind eye and didn’t investigate as intensely as he should have.
Fact: Anton Cermak was the real mayoral challenger to William Hale Thompson in 1929. Thompson’s “America First” and anti-immigrant positions were also real. William Hale Thompson was also known for having mobster ties and for being corrupt.
Fact: There was no bombing attempt on Anton Cermak’s life, and Bill Thompson wasn’t actually arrested. In fact, Thompson would go on to win the 1929 election, but would then lose to Cermak in the 1931. Sadly, Cermak did die in an assassination attempt in 1933. Cermak was at an event with President-elect Roosevelt, who the shooter claimed was the actual target.
Fact: The newspaper article about Al Capone’s arrest for having a concealed weapon is factual. This may seem like a small conviction, given that it was well-known he was a gang leader, but it was a big deal at the time. Capone was very difficult to convict. He avoided direct involvement in crimes, leaving little evidence linking him personally to illegal acts. He protected himself through widespread bribery of police, judges, and officials, and witnesses were often too afraid to testify. Capone also maintained public support by portraying himself as a charitable figure, while skilled lawyers exploited legal loopholes. Law enforcement lacked the tools to take on organized crime until federal agents shifted focus to tax evasion, which ultimately led to a more substantial conviction in 1931. He would stay in jail until 1939, when he was released due to poor health, and would remain out of the public eye and in declining health until his death in 1947, at the age of 48.
Fiction: The shadow organization we’ve named “La Famiglia” is fictional, though there were several other powerful gangs in Chicago other than Al Capone’s.
Fiction: The FBI was founded in 1908, but was known as the “Bureau of Investigation” (BOI) until 1935. We opted to keep the name “FBI” since this name change is not well-known and we didn't want to cause unnecessary confusion. :)
Materials
Baseball Cards:
The cards in your game are real baseball card images from the 1920s. All four players were on the Chicago Cubs in 1929. Charlie Grimm was the Cubs’ first baseman and would later become the Cub’s manager. Charles Leo "Gabby" Hartnett was a Hall of Fame catcher, and hit one of the most dramatic home runs in baseball history (the Homer in the Gloamin). Lewis "Hack" Wilson was a powerful slugger and Hall of Fame outfielder who set the still-standing single-season RBI record with 191 in 1930. Hazen "Kiki" Cuyler was a Hall of Fame outfielder.
Arlington Park Betting Cards:
Arlington Park was a real horse track that operated for nearly 100 years (1927-2021). After it opened, it quickly became a premier destination for horse racing and betting, offering a more regulated alternative to traditional bookmaking. The venue attracted both high society and everyday gamblers, and the betting rules in the game are the same that were in use in the ‘20s. The above image is from Arlington Park in 1927.
Club Poster:
Speakeasy clubs were secret, often hidden establishments that illegally sold alcohol during the Prohibition era in the United States (1920–1933). These underground bars flourished in cities across the country, offering jazz music, dancing, and cocktails behind unmarked doors and whispered passwords. They became cultural hotspots, blending glamour, rebellion, and a lively nightlife scene.
Jon Calloway (noted on the poster), was a well-known jazz pianist of the era, and was a frequent performer at several speakeasies in Chicago. His soulful style and improvisational flair made him a local legend in the underground music scene.
We sincerely hope you enjoyed the game! :D