It's easy to think of Hugh Hefner as a "playboy"; harmless to everyone but himself and the women he used; leading a fantasy lifestyle that every man secretly wishes was his alternative life.
But I think he was a destructive person. He made it "ok" for men to view pornography. He mainstreamed it. Albeit, his version was tame, but it is what the culture would tolerate at the time. The wretched excess that has come in the wake of Playboy is built on its foundation.