From what I remember about Lindsay he probably played this woman for a real sucker.
Speaking of others who knew who to hit on I just did an "equal time" search for Mayor Marion Barry and there's no more really great jogging tog shots (when he made his morning rounds to visit some voters) and his first couple of hundred are of him in a suit!
Even his arrest picture has him in a suit!
He was certainly far more colorful than John Lindsay but Google.com has reduced him to a mere cinder of his otherwise mercurial and highly likeable personality.