[1] Gessen's paternal grandmother Ester Goldberg, the daughter of a socialist mother and a Zionist father, was born in Białystok, Poland, in 1923 and emigrated to Moscow in 1940.

[5] Gessen's maternal grandmother, Ruzya Solodovnik, was a Russian-born intellectual who worked as a censor for the Stalinist government until she was fired during an antisemitic purge.

Gessen's maternal grandfather Samuil was a committed Bolshevik who died during World War II, leaving Ruzya to raise Yelena alone.

[20][21] In September 2012, Gessen was appointed as director of the Russian Service for Radio Liberty, a U.S. government-funded broadcaster based in Prague.

[23] In December 2013, Gessen moved to New York because Russian authorities had begun to talk about taking children away from gay parents.

In June 2013, Gessen was beaten up outside of the Parliament; they said of the incident: "I realized that in all my interactions, including professional ones, I no longer felt I was perceived as a journalist first: I am now a person with a pink triangle."

"[25] In a January 2014 interview with ABC News, Gessen claimed that the Russian gay propaganda law had "led to a huge increase in antigay violence, including murders.

It's led to attacks on gay and lesbian clubs and film festivals ... and because these laws are passed supposedly to protect children, the people who are most targeted or have the most to fear are LGBT parents.

[2] As of June 2023[update], Gessen taught as a distinguished professor at the Craig Newmark Graduate School of Journalism at the City University of New York.

[29] Previously at Amherst College, they were named the John J. McCloy '16 Professor of American Institutions and International Diplomacy for the 2017–18 and 2018–19 academic years.

[31] In August 2023,[32] Russia opened a criminal case against Gessen on charges of spreading "false information" about the Russian army's actions in Ukraine.

[33] Gessen was accused of spreading "false information" after discussing atrocities in the Ukrainian city of Bucha during an interview with Russian journalist Yury Dud.

[35] In August 2023, the Heinrich Böll Foundation (HBS) announced that Gessen was the winner of the Hannah Arendt Prize for Political Thought.

Gessen was also critical of the Israeli bombings of the Gaza Strip, which they considered to be highly destructive and comparable to an Eastern European ghetto "being liquidated" by the Nazis.

[50] In The Man Without a Face, Gessen offers an account of Putin's rise to power and summary of recent Russian politics.

"[63] When this book was published in 2014, A. D. Miller wrote in the Telegraph that "even readers who do not share Gessen's esteem for Pussy Riot as artists will be convinced of their courage".

[68] Published in April 2015 by Riverhead, The Brothers investigates the background of Dzhokhar and Tamerlan Tsarnaev, the perpetrators of the Boston Marathon bombing.