- founded Playboy Magazine in 1953 at age 27.

- Playboy was not the first magazine with erotic nudity, but it was the first to sell through mainstream media channels.

- "Anti-puritanism" was a theme throughout his life. It drove his interest in freedoms and against repressions like censorship, segregation, and sexual inhibitions.

- claimed to be descended from the Puritan governor of the Plymouth Colony, William Bradford. (Hence the backlash, is the idea.)

- He was considered an early libertarian.

- He gave fellow Enemy, Dick Gregory, his big break in 1961. Gregory gave him a big hug at his NY Friars Club Roast in 2001.

- Donated consistently to Democratic presidential candidates.

- He is on the Second List under "McGovern Staff Members and Campaign Contributors." So, his inclusion is probably due to his public donation record and nothing else. His name appears nowhere else in the Watergate testimony.

- In a National Security Archives Project interview in 1999, he said, "I was on the enemies list during the Nixon era because I was supporting and donating funds to more liberal democratic, democrat causes...."

- The Washington Post noted his inclusion on the List in his obituary, but not the NY Times. The Post also noted that he had been investigated by the FBI which would have been a much more disturbing thing than just being named on the Enemies List.

- 1974--the year Nixon resigned--was the turning point for Hefner. The sexual revolution helped women, he rightly noted, but by 1974 there was a lot more to do and he never noticed it. The role of women was not as narrow as before, but it was still narrow. 1974 was the peak circulation for Playboy. It's a coincidence that it's the year Nixon resigned--or maybe not so much. 1974 was the year that executive secretary and former "bunny," Bobbie Arnstein, was arrested for possession by the FBI. She committed suicide in January 1975, creating bad publicity. Nothing was not complicated back then. Hefner did remarkable things pre-1974 to question authority in enduring ways. Pretty much no one celebrates his post-1974 activities. He was on the mere Second List for mere financial support, but his early legacy of social progress highlights the wrongness of Nixon's social agenda. Nixon never tried to help women; Hefner sort of did try and did succeed a little bit.