Al Capone, Norman Tweed Whitaker, Chess, and Taxes


In the United States, tax returns typically must be filed by April 15. The FBI describes Al Capone as having run an empire of crime, including robbery, narcotics trafficking, and murder. Yet the main charge against Al Capone was tax evasion.

Part of Capone’s sentence was served on Alcatraz Island, where chess master Norman Tweed Whitaker was a fellow inmate. Willie Harris, a journalist living in Denton, Texas, investigated this chess and crime connection. He shared his research with William Root, Alexey Root’s son, and parts are presented here.

College Chess

Harris wrote, “Norman Tweed Whitaker learned to play chess at the age of 14. He earned a bachelor’s degree in literature from the University of Pennsylvania and a law degree from Georgetown University. As an undergraduate, he represented the University of Pennsylvania in chess matches and contests.”

Shady Side: The Life and Crimes of Norman Tweed Whitaker, Chessmaster

John S. Hilbert wrote the authoritative biography Shady Side: The Life and Crimes of Norman Tweed Whitaker, Chessmaster, which includes 570 games. However, the following game is not in Hilbert’s book. The game is provided courtesy of Neil Brennen and Hilbert and originally appeared in the Philadelphia Item, May 29, 1910.

Alcatraz Island Federal Prison

Harris wrote, “Whitaker spiraled down into the world of crime, eventually sentenced to time at the federal prison on Alcatraz Island. At Alcatraz, Whitaker crossed paths with Al Capone.” Here is an FBI webpage on Al Capone, which states in part:


On June 16, 1931, Al Capone pled guilty to tax evasion and prohibition charges. He then boasted to the press that he had struck a deal for a two-and-a-half year sentence, but the presiding judge informed him he, the judge, was not bound by any deal. Capone then changed his plea to not guilty.
On October 18, 1931, Capone was convicted after trial and on November 24, was sentenced to eleven years in federal prison, fined $50,000 and charged $7,692 for court costs, in addition to $215,000 plus interest due on back taxes.

According to an inflation calculator, Capone’s interest due on back taxes of $215,000, in 1931 dollars, is the equivalent of $4,096,297 in 2024 dollars.

Hilbert emailed, “Capone refused to join a Whitaker-led hunger strike at Alcatraz, that resulted in Whitaker not thinking highly of Capone, and Whitaker being fed by a rubber tube through his nose for a short time.”

Brilliant Minds Drawn to Crime

Harris observed, “The most brilliant of minds are prone to folly and drawn to the road of temptation.”

Hilbert wrote: Whitaker, certainly, whether genius or not, was just such a one. He had so many advantages in life: raised in a prosperous, middle-class family, the eldest son of a Philadelphia high school principal and a doting mother, He excelled at all he attempted, including chess. He summered at his family’s second home at the New Jersey shore, and by the age of twenty-three had begun a career as a federal attorney, specializing in patent law. The future was his to shape. And shape it he did, in such a crooked and immoral way, with criminal convictions landing him in Leavenworth, Alcatraz, and other prisons in Pennsylvania and Florida. His folly cost him his law license, his career, the trust of his loved ones, and his reputation.

William Root

William Root was a public school music teacher. William also taught chess in schools and camps. Now, he works in a library. His US Chess rating is 1743.

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