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Hugh Hefner was many things to many people: a playboy; a publisher; a philanthropist; a pornographer, to name but a few. But he was also a staunch advocate for social justice, especially as it related to Black folks. His civil rights activism and efforts to foster both Black rights and talent has many times been absent from the conversation about his life, which came to an end Wednesday night when his death was announced.

Playboy magazine was founded without the expectation that it would “solve any world problems or prove any great moral truths,” but the same was not true for Hefner’s personal life, which included associations with important and historical Black figures ranging from Dr. Martin Luther King, Jr. to Malcolm X to Dick Gregory to Alex Haley, and many more.

READ MORE: Hugh Hefner, Playboy Founder, Dead At 91

As such, here are five of Hef’s most woke, pro-Black moments.

1. He worked to end segregation with Dr. King.

“When Dr. King came to the Playboy Mansion, he was in Chicago specifically to deal with the segregation that existed in Chicago,” Hefner told CBS Los Angeles in 2011. “And that is really how I met Jesse [Jackson] and I was very actively involved after King’s death in the funding of PUSH and the Rainbow Coalition.”

2. He championed Black talent at a time when the world largely shunned it.

Hefner gave many Black performers their big break by inviting them to perform at his clubs. Dick Gregory recalled how Hef’s platform extended to Black people was than just about entertainment and a career.

“You had a courage when no one was bringing in blacks and minorities, and let you stand flat-footed in America and just talk, you brought me in” Gregory told Hefner during a roast of the Playboy founder in 2001. “I come here tonight not to roast you, but to say that had you not had the guts back then, we black comics that the world has been able to look at and understand our genius, we would be in some pot, roasting in debt, knowing we were never going to make it.”

3. Hefner once quit a job because he was “asked to discriminate against Black candidates,” the New York Times reported in its obituary.

4. Hef donated $25,000 as a reward for information surrounding the killings of three civil rights activists in 1964 after Gregory brought attention to the case. The donation prompted the FBI to offer its own reward, which led to a tip that was the break investigators needed.

“Hefner understood what those rednecks didn’t: that things had changed,” Gregory told British GQ in 2011. “That you could no longer argue that you’d ‘killed three Jews’. Or ‘killed three blacks’. What you’d done was, you’d killed three fellow human beings.”

5. Playboy published Dr. King’s final piece of written correspondence.

King wrote a letter to Playboy about the “struggle for racial justice, according to the King Center. Playboy in turn wrote back telling King in part that “Hefner shares many of you concerns and commitments” while appealing for permission to publish the letter.


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