Herman Cain in his office in Stockbridge, Ga. on April 17, 2019.
Melissa Golden—Redux
July 31, 2020 2:20 PM EDT

Herman Cain remembered the 1996 moment that changed his political trajectory as clearly as any in his life.

The businessman was advising Jack Kemp’s vice-presidential campaign and accompanied the boss to the iconic Sylvia’s soul food restaurant in Harlem for an event. A man in the crowd shouted out to Cain and his colleagues: “Black Republicans? There’s no such thing.” The same man, in Cain’s telling, called them “Uncle Toms.” The episode so angered Cain that when he got home from that campaign swing, he switched from a registered independent to a card-carrying member of the Republican Party. And over the next quarter-century, the child of the segregated South became one of the best-known Black Republicans in the country, briefly rising to be his party’s presidential frontrunner for the 2012 nomination and remaining one of the most quotable stars in conservative media.

So committed to his party’s stick-it-in-the-eye ethos was Cain that he flew to Tulsa, Okla., for President Donald Trump’s first return to the campaign trail after 100,000 U.S. coronavirus deaths, despite dire warnings from public health experts. At that indoor rally on June 20, the stage 4 colon cancer survivor posed for pictures without wearing a mask and sat in the packed stands with fellow fans of the President. On June 29, Cain tested positive for the coronavirus. On July 2, his aides announced he had been hospitalized. While fighting the disease, his Twitter account continued to criticize mask-wearing and to promote unproven endorsements of hydroxychloroquine. On July 30, Cain aides announced he had died. From the White House, Trump attributed the death to “the thing called the China virus.” Cain, among the most prominent Americans to die during this pandemic, was 74.

In many ways, Cain and Trump were cut from the same cloth. Neither had been elected to any political post before running for the White House. Both delighted in needling the Republican Party’s establishment and the mainstream press. They shot from the hip, campaigned in slogans and didn’t much care to learn the details. Both men were dogged by allegations of sexual affairs and inappropriate behavior, and both denied the allegations; they proved disqualifying for Cain—who ended his bid in December 2011 under intense scrutiny—but they did not derail Trump just one election cycle later. They were also both savvy exploiters of the media, often saying things they knew would provoke outrage and thus amplify the celebrity at the core of their bids. Indifference toward—if not hostility against—what had come before was a cornerstone of their strategy, not a flaw.

Cain was born in Memphis in 1945 to a domestic worker mother and a janitor father. When his dad was hired to be the chauffeur for the head of Coca-Cola, the family moved to Atlanta, where Cain would graduate from Morehouse College. He then completed his graduate studies at Purdue University after civilian service in the Navy. From there, Cain moved from engineer to executive with Pillsbury and its subsidiaries of Burger King and Godfather’s Pizza, where he would be its C.E.O. In 1988, he oversaw Godfather’s buyout from Pillsbury. Throughout the same time, he held positions with the Federal Reserve Bank of Kansas City. That part of his resumé led Trump to consider Cain for a position in his Administration, a move that drew dissent from fellow Republicans who were not eager to revisit the allegations against Cain. For three years, Cain led the National Restaurant Association, a lobbying arm for the industry that paid settlements to at least two women who detailed Cain’s unwanted advances.

His was not a typical career in his post-C.E.O. years. Cain became a sought-after motivational speaker, an unsuccessful presidential candidate in 2000 and a Senate one in 2004. As the Tea Party movement started to organize after Barack Obama’s election to the White House, Cain emerged as one of its strongest spokespeople. When the 2012 election cycle began, Cain decided to run the scrappiest of campaigns focused on an untraditional travel schedule that often seemed more like a book tour than an organizing effort. His novel “9-9-9” tax plan—proposing a 9% corporate business flat tax, a 9% personal income flat tax and a 9% national sales tax—drew eye-rolls from economists but curiosity from voters. Antipathy toward frontrunner Mitt Romney proved sufficient to give Cain a chance to rise in the late summer and fall of 2011, until his personal life just proved too much. But he didn’t shrink from public life. Instead, he became a ubiquitous voice and reliable critic of Democrats.

He’ll perhaps remain best known, though, for his tax plan that made little sense to most economists. Even with his death, the “9-9-9” sloganeering stayed on the front-burner. On Twitter, Romney took one last good-natured jab at the tax plan: “St. Peter will soon hear ‘999!’ Keep up the fight, my friend.”

Write to Philip Elliott at philip.elliott@time.com.

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