J. Edgar Hoover, left, and Dick Gregory in 1968. (AP)

In the middle of the hothouse atmosphere of the 1968 U.S. presidential election — racial strife splitting cities, antiwar protests on college campuses, segregationist George Wallace growling up out of the South — Dick Gregory barnstormed the country, pitching audiences his acid mix of jokes and politics. The African American comic and activist was looking for votes in his long-shot bid as a write-in candidate for the White House.

“I have a lot of newsmen asking me strange questions,” Gregory told a group of students at the University of California at Los Angeles on April 24. “Like for instance, ‘Mr. Gregory, if you were elected president of the United States, what is the first thing you would do?'” The punchline: “I thought the whole world knew if I was elected president of this country, the first thing I’d do is paint the White House black.”

A few nervous laughs, scattered claps.

“The second thing I’d do is bring all the boys home from Vietnam,” Gregory announced. “And send LBJ.”

Gregory’s caustic style, marrying humor and hard truths about race and politics, was the main theme of the tributes that popped up in the wake of the news of his death over the weekend at age 84. But during the chaotic summer feeding into the 1968 election, Gregory’s strong critique drilled to the heart of the political system.

“I feel that the two party system is obsolete,” he said in another 1968 interview. “The two party system is so corrupt and immoral, they cannot solve the problems confronting the masses of the people in this country.”

Gregory’s radical criticism was also putting him in a dangerous spot. As he campaigned, the comic fell into the paranoid crosshairs of J. Edgar Hoover, and the FBI director concocted a strange plan to potentially “neutralize” Gregory with the help of the Mafia.

The scheme would not emerge publicly until 10 years later, when files related to the bureau’s controversial surveillance activities on black radical and civil rights groups were first released.

“Do you realize what you have here?” Gregory said in 1978 when presented with Hoover memos tied to the effort. “This piece of paper has the director of the most powerful police agency in the history of this planet proposing to contact this Mafia so they could work together.”

According to a 1978 account in The Washington Post, a month after Gregory’s 1968 appearance at UCLA, Hoover sent a memo to Martin W. Johnson, the head of the Chicago FBI office, instructing the agent to “develop counterintelligence measure to neutralize” the comedian.

“Gregory has traveled all over the country preaching black nationalist extremism, hatred and violence,” Hoover wrote. “Gregory uses his reputation as a … comedian to insure his vitriolic statements are reported by the press. He has made personal attacks on the President of the United States and the director of the FBI and on FBI agents.”


Activist Dick Gregory holds what he calls his FBI files outside FBI headquarters in Washington on April 3, 1998. (Dennis Cook/AP)

The FBI director, however, warned Johnson that the agency’s actions “should not be in the nature of an exposé, since he already gets far too much publicity. Instead, sophisticated, completely untraceable means of neutralizing Gregory should be developed.”

Hoover worked out the idea in a memo dated three weeks later on May 15, 1968. Gregory, Hoover noted, had made harsh comments about members of the Mafia, then known as the Syndicate. “Syndicate hoods are living all over,” the comedian had told a crowd. “They are the filthiest snakes that exist on this earth.”

Although the FBI director had previously vehemently denied the existence of organized crime, Hoover saw an opportunity here. He ordered the head of the Chicago office to “Consider the use of this statement in developing a counterintelligence operation to alert La Cosa Nostra (LCN) to Gregory’s attack on LCN,” the director wrote. “It is noted that other speeches by Gregory also contained attacks on LCN.”

Whether the bureau successfully baited organized crime into reprisals against Gregory is unlikely. Hoover died in 1972, before the memos became public. In 1978, Johnson, the former Chicago field office head, told The Post he did not recall anything regarding Gregory: “I don’t remember anything, and even if I did I couldn’t say anything because I’m still bound by my oath of office not to disclose anything we did.”

FBI schemes against civil rights leaders were part of the agency’s “COINTELPRO” operations that started in 1956 and continued until 1971. For example, FBI documents unearthed during a U.S. Senate investigation in 1975 showed officials seeking “avenues of approach aimed at neutralizing” Martin Luther King Jr. “as an effective Negro leader.”

In King’s case, neutralizing meant, among other things, an effort to get King to kill himself, by sending him an anonymous letter threatening to expose his “adulterous acts” and “immoral conduct.”

By 1978, Gregory had left comedy for full-time activism and political commentary. “Instead of being outraged at what I said, Hoover should have given me a medal,” he told The Post.

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J. Edgar Hoover saw Dick Gregory as a threat. So he schemed to have the Mafia ‘neutralize’ the comic.