In
The Natural, his book about the Clinton presidency, Klein gave a mixed assessment of Clinton's time in office. In the book, he wrote: "the conventions of journalism prevent me from fitting too neatly into one political niche (although as a columnist for the New Yorker and Newsweek my predilections are obvious)". Klein's depiction of the Clinton presidency also gave a detailed examination of the moderate Democratic positions espoused by the Democratic Leadership Council, as well as third way politics generally, of which Klein was highly complimentary.
He is an admirer of George W. Bush personally, although he has sometimes disagreed with his policies. In an interview with Hugh Hewitt Klein said of Bush, "Let me say that of all the major politicians I've covered in presidential politics in the last two or three times around, he is the most likely to stick with an issue, even if the polls are bad, and to govern from the gut as you said. I don't always agree with the decisions that he makes, but I think he is an honorable man, and when I've criticized him, I've tried to criticize him on the substance, and certainly not on his personality, because I really like the guy."
In 2008, Klein caused controversy with comments on the motivations of neoconservatives, when he said:
American foreign policy scholar Max Boot and the Anti-Defamation League National Director, Abraham Foxman, were among the critics of Klein's views. Klein is also frequently criticized by Bob Somerby, a media commentator.
In May 2009 he invited further controversy when he was quoted in an article in Politico.com, wherein he stated that the reasoning and ideas of prominent conservative commentator Charles Krauthammer were of limited value because of Krauthammer's wheelchair use:
"There's something tragic about him... His work would have a lot more nuance if he were able to see the situations he's writing about."
Klein has been criticized by several conservative publications for accusing Fox News host Glenn Beck, Republican Senator Tom Coburn and former Alaskan Governor Sarah Palin of sedition.
Joe Klein wrote the following in Time Magazine, September 13, 2010, In the Arena, "Tough Issues. What if we gave people real choices and real consequences and let them make decisions?" In this article, Klein writes the following: "By most accounts it has succeeded brilliantly, even though the participants are not very sophisticated: 60% are farmers."