John Santucci, who portrays Ray Luca's sidekick Paulie Taglia, was a real-life professional thief whom was busted on numerous occasions by series co-creator Chuck Adamson and star Dennis Farina when they were Chicago Cops. Many of the robberies, hijackings, and burglaries are based upon Santucci's crimes, including the museum jewelry heist profiled in the pilot movie according to the DVD Liner notes.
When the story was first brought to producer Michael Mann, he said he thought the best way to tell the story was as a weekly series. He said he considered doing it as a feature film or a made for television movie as well.
The character of Ray Luca (Anthony Denison) is based upon Chicago mobster Tony "The Ant" Spilotro. Spilotro also inspired Joe Pesci's character of Nicky Santoro in "Casino". By the same token, Andrew "Dice" Clay's character of Max Goldman and Robert DeNiro's character of Sam "Ace" Rothstien in "Casino" are both based upon Spilotro's partner, Frank "Lefty" Rosenthal.
Nate Grossman (Steve Ryan), a member of Torello's MCU, is based upon a real detective of the same name who worked with co-creator Chuck Adamson and star Dennis Farina. In real life, Grossman was killed in the line of duty.
The character of burglar Frank Holman is based upon 'Frank Hoheimer', a famous Chicago burglar busted by series co-creator Chuck Adamson. Michael Mann, the series producer previously used the famed criminal as the basis for his movie "Thief".
Since both "Crime Story" and Miami Vice (1984) were produced by Michael Mann, both series shared the same technical advisers, directors, and crew members. And if you watch both series, both shows share the same supporting actors and guest stars as well.
The character of Manny Weisborn (Joseph Wiseman), Miami crime lord and Luca's mentor, was based on Meyer Lansky. Throughout the series, Weissborn is always making references to Lansky's New York associates like "Lucky" Luciano, "Bugsy" Siegel, and Frank Costello.
During the first season, it is established that Lt. Michael Torrello served in the Army during the Korean War. In the first season episode Crime Story: Torello on Trial (1987), we learn that he was awarded the Bronze Star and the Purple Heart.
The "Orbit Room" bar plays a recurring role throughout much of the first season, as the MCU cops' off-duty haunt. The real-life Orbit Room was a new, retro-themed bar which opened at 3708 N. Broadway, Chicago in April 1986, shortly before filming began, and closed its doors just two years later.
The trivia item below may give away important plot points.
In the episode where Ray Luca goes to the home of mob boss Dominic Tranchita and shoots him with a silenced .22 pistol while Tranchita's eating sausages, that incident is based upon how Chicago mob boss Sam Giancana was killed.