[7] In April 2016, he rose to prominence after resigning from the Observer over the newspaper's close relationship with Donald Trump, the Republican presidential candidate.

[8][9][10] The Observer's executive editor, Ken Kurson, revealed in a magazine interview he advised Trump on a speech the candidate delivered before the American Israel Public Affairs Committee.

Announcing his resignation the day after the Observer endorsed Trump in the New York Republican primary, Barkan later told CNN "a line had been crossed and I thought it was time for myself to depart.

"[11] As a columnist and freelance reporter, Barkan has contributed to the Village Voice, The Guardian, The Washington Post,[12] The New Yorker,[13] The New York Times, The Nation,[14] Reuters, Esquire, GQ, New York Daily News, Daily Beast, The Baffler,[15] the Los Angeles Review of Books, and the Columbia Journalism Review.

[32][33][34] Barkan's campaign was managed by future-Assemblymember Zohran Mamdani[35][36] and endorsed by the New York Daily News and local politicians such as Squad member Alexandria Ocasio-Cortez, but he lost the September 2018 Democratic primary to Andrew Gounardes by 15 percentage points.