The Tangled Web

The Life and Death of Richard Cain-Chicago Cop and Hitman

Foreword by Jack Clarke
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About The Book

The Tangled Web tells the dramatic story of Detective Richard Cain, the man the FBI described as “possibly the most corrupt police official in the history of Chicago.” Cain led a double life—at once a chief investigator and a “made” man, both a detective who led raids on gambling rings and a soldier carrying out hits for Mafia bosses. Using years of research, interviews, family anecdotes, and rare documents, Michael Cain creates a comprehensive and compelling biography of his half-brother. This edition features an all-new introduction by the author. In a story that reads like the plot of Martin Scorsese’s The Departed, Cain played both ends against the middle to become a household name in Chicago and a notorious figure in both the Mob and the world of Chicago law enforcement. Before his execution by shotgun in Rose’s Sandwich Shop, Cain’s legend would grow to the point of rumored involvement in the assassination of John F. Kennedy and the FBI’s plot to assassinate Fidel Castro. Filled with fascinating and until-now unknown facts, The Tangled Web tells the full story of this one-man crime wave.

Product Details

  • Publisher: Skyhorse (February 20, 2018)
  • Length: 256 pages
  • ISBN13: 9781510722811

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Raves and Reviews

“A must read for folks following organized crime in America.”
—Ray Gibson, Chicago Tribune

“Richard Cain embodied the symbiotic relationship of Chicago’s legendary Outfit and the political machine that ran the city. . . . Great stuff for a look at the reality of life in the Mob and a window on how the ‘city that works’ really worked.”
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