[6] In 1964, he graduated with honors, obtaining a Bachelor of Arts degree from the University of Wisconsin–Madison, where he served as editor-in-chief of the Daily Cardinal.

Greenfield assisted with RFK's speech, "On the Mindless Menace of Violence", that he delivered the day after Martin Luther King Jr.'s assassination.

[7] Greenfield was chief speechwriter for New York City Mayor John Lindsay and also worked for seven years with political consultant David Garth.

[5] Over the course of his journalistic career, Greenfield has reported mainly on domestic politics and the media, with occasional pieces on cultural matters.

For five seasons, he hosted the national public television series "CEO Exchange" where he featured in-depth interviews with high-profile chief executive officers.