Much of our views of Hef are in the light of history, which certainly shines differently than that of the present. Hef was THE iconic Playboy of the 50's & 60's, intentionally modeling himself and his lifestyle after the images of James Bond (the playboy, not the spy) and others of the time. He had what most of us guys in those days wanted: girls, fast cars, girls, good liquor, girls, natty clothes, girls.... and that's what sold the mag and him. As the years went by, his image tarnished for various and good reasons.
Using Hef to sell a pipe was no different than the many uses of celebrities to do the same thing today. Remember, OJ was used to sell a lot of things too, until his mistakes caught up with him.