[6] On March 16, 2009, Chait appeared on Comedy Central's The Colbert Report to counter conservative arguments that the New Deal was a failure.

Chait joined the staff of New York magazine on September 6, 2011, leaving his post as senior editor of The New Republic.

A self-described liberal hawk,[9] he has written pieces critical of left-wing figures such as Naomi Klein and wrote a New Republic cover article condemning Delaware's tax haven policies.

He strongly criticized the editorial staff of The Detroit Free Press after a controversial article by Michael Rosenberg that alleged systematic infractions of NCAA rules by the university's football team under former head coach Rich Rodriguez.

"[16][failed verification] Chait then claimed Rosenberg's allegations that Rodriguez "operated a football sweatshop has been totally debunked.

"[17] On September 26, 2011, Chait wrote a column about John Mearsheimer's blurbs about Gilad Atzmon's book, The Wandering Who.

[18] On January 27, 2015, Chait wrote an article for New York magazine on political correctness, which he labeled "a system of left-wing ideological repression" and cited examples from academia and social media.

[25][26] On January 14, 2019, he accused Senator Elizabeth Warren of selling out to "powerful interests" for her opposition to an initiative which would have expanded the number of charter schools in Massachusetts.

[27] Writer Alexander Russo criticizes Chait for not consistently disclosing his wife's charter school advocacy.