He won a National Book Award in 1974 (category, "Contemporary Affairs") for The Briar Patch: The People of the State of New York versus Lumumba Shakur, et al.[1] Reprinted, 1997, with new subtitle The Trial of the Panther 21.

He won a Pulitzer Prize (category, "Commentary") in 1985 "for witty and insightful reflection on public issues in 1984 and throughout a distinguished career."

After his graduation in 1939, he worked for a short time as a labor organizer, then joined the staff of the New York Post, earning a reputation for a quietly elegant prose style that featured long but rhythmic sentences, a flair for irony, and gentle, almost scholarly sarcasm.

He was shown that way in television spots that promoted the New York edition of Newsday in which Kempton brought his bicycle to a stop at an intersection and deadpanned, "I guess I've been around so long that people think they have to like me."

Ten years later, he received the Elijah Parish Lovejoy Award as well as an honorary Doctor of Laws degree from Colby College.

He was so known for his rococo style that in his essay collection Hooking Up (2000), Tom Wolfe wrote, "Kempton used so many elegant British double and triple negatives, half the time you couldn't figure out what he was saying."

"[6] Journalist David Halberstam credited Kempton with pioneering the genre of New Journalism through his "short story"-like installments in his columns.