After graduating from the University of Michigan, he moved to Israel. He spent a decade in the army, government service and politics. In 1977, he was appointed director of the Government Press Office, a post he held for five years during the administration of Prime Minister Menachem Begin. Chafets was an active participant in the Egytian-Israeli peace process and a delegate to the first Israeli-Egyptian peace negotiations.

He was the founding managing editor of the Jerusalem Report magazine and is the author of twelve books of fiction, media criticism, and social and political commentary, three of which have been named Notable Books of the Year (by The New York Times). He is also the recipient of the 2008 Wilbur Award for his book A Match Made In Heaven.

He was a regular columnist for the New York Daily News from 2000 until 2004. Today his columns appear frequently in major newspapers around the world, including The New York Times, the Los Angeles Times and the New York Post. He is a frequent contributor to the New York Times Sunday Magazine. In 2008, his NYT Magazine cover story on Mike Huckabee was a finalist for the National Magazine Award.

Chafets is a spirited political polemicist. A strong supporter of Israel, he has been a vocal critic of Arab dictatorships, Islamic radicalism, extremist groups such as Hizbollah and Hamas, and what he perceives as a pro-Palestinian bias in academia and the media. He is also well-known for his opposition to the role of religious political parties in Israel.

After the first primaries of the 2010 U.S. election season, Chafets identified Rush Limbaugh as "the brains and the spirit behind" the Republican Party's "resurgence" in the wake of the 2008 election of President Barack Obama. Among other specifics in the May, 2010 op-ed column, Chafets pointed to Sen.Arlen Specter, who was defeated in a Democratic primary in Pennsylvania: Limbaugh had labeled him, when Specter was still a Republican, "Republican in Name Only." Chafets also reported that Sarah Palin's "biggest current applause line ... Republicans are not just the party of no, but the party of hell no ... came courtesy of Mr. Limbaugh." More generally, Chafets wrote, Limbaugh has argued the party-of-no Ronald Reagan conservative course for the Republicans vigorously, notably since six weeks after the Obama victory, and has been fundamental to, and encouraging to, the more prominently noted Tea Party movement. Limbaugh is the subject of Chafets' 2010 book Rush Limbaugh: An Army of One.

Seven works of non-fiction

1. Double Vision: How America's Press Distorts Our View of the Middle East (1985)
2. Heroes and Hustlers, Hard Hats and Holy Men (1986)
3. Members of the Tribe (Bantam Hardcover- 1988)
4. Devil's Night: And Other True Tales of Detroit (1990)
5. A Match Made in Heaven: American Jews, Christian Zionists, and One Man's Exploration of the Weird and Wonderful Judeo-Evangelical Alliance (HarperCollins Hardcover - Jan 9, 2007)
6. Cooperstown Confidential: Heroes, Rogues and the Inside Story of the Baseball Hall of Fame (2009, Bloomsbury USA)
7. Rush Limbaugh: An Army of One (2010)

And five novels

1. Inherit the Mob (Random House)
2. The Bookmakers (Random House)
3. The Project (Warner Books)
4. Whacking Jimmy (as William Wolf) ((Villard))
5. Hang Time (Warner Books)