Rudy Giuliani sent Trump business rival Leona Helmsley to prison for tax fraud

New York is America's largest city, but sometimes it feels like it keeps recycling the go-go '80s with a tiny cast of characters. On Thursday, New York prosecutors charged the Trump Organization and its longtime CFO, Allen Weisselberg, with 15 counts of tax-related felonies. They pleaded not guilty.

The alleged tax fraud scheme, as laid out by prosecutors, is actually pretty simple: the Trump Organization used company money to pay Weisselberg's rent, car lease, and other personal expenses, allowing him to avoid paying federal and local taxes, and kept track of the money in a secret ledger.

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Helmsley, who died in 2007, was a greed-is-good tabloid-staple real estate magnate who served 19 months in prison after being convicted of tax fraud in 1989. She and her husband, Harry Helmsley, renovated their Greenwich, Connecticut, mansion with millions siphoned from their hotel and real estate empire, which included the Empire State Building, among other properties.

The prosecutor who sent Helmsley to jail was Rudy Giuliani, then the crusading U.S. Attorney for the Southern District of New York. When Helmsley appealed her conviction, her lawyer was Alan Dershowitz. And Donald Trump himself kicked Helmsley when she was down, leaking a letter to the New York Post in 1988 amid an easement dispute over an Atlantic City property Trump bought from Penthouse magazine.

Howard Kurtz, now a Fox News media critic, contemporaneously described Trump's "deliciously vitriolic letter" to Helmsley in The Washington Post, saying it revealed Trump's "previously hidden capacity for venom." In the letter, Trump called Helmsley "a disgrace to the industry and a disgrace to humanity in general," and told her that without her husband, she "would not be able to randomly fire and abuse people in order to make yourself happy."

What Helmsley was convicted of and Trump's company indicted for is "the kind of crime that super-rich people think they can get away with — and that they can get caught for, particularly if they are brazen about it," Rachel Maddow said on MSNBC Thursday night. And "comically high-profile people" aren't exempt.

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Peter Weber, The Week US

Peter has worked as a news and culture writer and editor at The Week since the site's launch in 2008. He covers politics, world affairs, religion and cultural currents. His journalism career began as a copy editor at a financial newswire and has included editorial positions at The New York Times Magazine, Facts on File, and Oregon State University.