Cooper, who now heads the magazine empire, likens the US president’s leadership style to the populist politics played out in America in the ‘50s under Eisenhower.
Speaking just a few weeks before the death of his father Hugh Hefner, Cooper Hefner said the Playboy cover which featured Donald Trump was now a “personal embarrassment” for both him and the company’s brand.
Mr Trump appeared on the front of the March 1990 edition of the erotic magazine dressed in a white tuxedo shirt and bow-tie, alongside playmate Brandi Brandt.
But Cooper said that the cover photograph featuring a young Trump in a suggestive pose was offensive to him because he didn’t like the now-US president’s populist politics.
He compared his leadership to Eisenhower’s conservative style in the fifties, during which thousands of Americans were interrogated over alleged links to communism.
Mr Trump is accused of pandering to right-wing voters on issues such as immigration – including his pledge to build a wall along the US’s southern border with Mexico.
Mr Hefner, 25, a self-confessed liberal, said: “We don’t respect the guy.” He told The Hollywood Reporter: “There’s a personal embarrassment because Trump is somebody who has been on our cover.”
Mr Hefner senior founded Playboy in 1953 as a reaction to what he saw as the culturally-stiff times. The first edition featuring a nude Marilyn Monroe – pictures that had been taken some years earlier – caused shock in the conservative era.
The erotic magazine is credited in some circles for helping with the liberation of women, though others have criticised its role in sexualising and objectifying particularly the female workers of the Playboy Mansion.
Cooper took over the running of the Playboy empire from his father last year and believes he can again use the brand to bring about what he sees as a further shift in society.