[6] Taibbi became known for his brazen style, having branded Goldman Sachs a "vampire squid" in a 2009 article about the Wall Street firm's outsized role in the 2008 financial crisis.

Taibbi has authored several books, including The Great Derangement (2009); Griftopia (2010); The Divide (2014);[15] Insane Clown President (2017); I Can't Breathe (2017); and Hate Inc. (2019).

[14] He first attended New York University but was "unable to deal with being just one of thousands of faces in a city of millions" and transferred after his freshman year to Bard College, where he graduated in 1992.

[22][2] In the early 1990s, Taibbi moved from Saint Petersburg, Russia to Tashkent, Uzbekistan,[1] where he began selling news articles more regularly.

In 1997, he left the tabloid Living Here and joined Mark Ames to co-edit the English-language Moscow-based, bi-weekly free newspaper, The eXile,[2][1] which was written primarily for the city's expatriate community.

For example, a regular column reported on a member of staff at The eXile hiring a Russian prostitute and then writing a long "review" of the woman and the details of the sexual encounter.

[6] In 2010, journalist James Verini wrote in Vanity Fair that during an interview in a Manhattan restaurant, he told Taibbi that The Exile was "redundant and discursive".

[39] In a Facebook post responding to the controversy, Taibbi apologized for the "cruel and misogynistic language" used in the book, and said the work was conceived as a satire of the "reprehensible" behavior of American expatriates in Russia and that the description of events in the chapter was "fictional and not true".

In March 2005, Taibbi's satirical essay, "The 52 Funniest Things About the Upcoming Death of the Pope",[44] published in the New York Press, was denounced by Hillary Clinton, Michael Bloomberg, Matt Drudge, Abe Foxman and Anthony Weiner.

[45] Taibbi defended the piece as "off-the-cuff burlesque of truly tasteless jokes," written to give his readers a break from a long run of his "fulminating political essays".

[53] Taibbi covered the 2008 United States presidential election in Year of the Rat, a special Rolling Stone diary.

[62] In February 2014, Taibbi left Rolling Stone and joined First Look Media to head a financial and political corruption-focused publication, Racket.

[63] However, after management disputes with First Look's leadership delayed its launch and led to its cancellation, Taibbi returned to Rolling Stone the following October.

[66][67][68] The podcast has since featured interviews with various guests including Liz Franczak,[69] Andre Damon,[70] David Dayen,[71] Cornel West,[72] Glenn Greenwald,[73] and Aaron Maté.

[76] In 2018, Taibbi began publishing a novel, The Business Secrets of Drug Dealing: Adventures of the Unidentified Black Male, as a serialized subscription via email and a website with an anonymous partner.

Taibbi stated that his decision to move his writing to a self-published newsletter service was made independently and that he was not asked to leave Rolling Stone.

Other contributors include Emily Bivens, Andrew Lowenthal, Jared Moore, cartoonist Daniel Medina and Matt Orfalea.

[92][93] Jeffrey Blehar, writing for National Review, said that Taibbi's reporting "contained few, if any, explosive revelations for people who have been tuned in to the debacle surrounding Twitter's suppression of the New York Post story on Hunter Biden's laptop".

[96][better source needed] The sixth installment, released on December 16 by Taibbi, described how the FBI contacted Twitter to suggest that action be taken against several accounts for allegedly spreading election disinformation.

[97][98][better source needed] Taibbi's ninth installment, released on December 24, relates to the CIA and FBI's alleged involvement in Twitter content moderation.

[99][better source needed] The fifteenth installment, released on January 27, 2023 by Taibbi, reports on the Hamilton 68 Dashboard maintained by the Alliance for Securing Democracy.

[101][non-primary source needed] The seventeenth installment, released on March 2, by Taibbi, reports on the Global Engagement Center, which was established by the Countering Foreign Propaganda and Disinformation Act.

[103] On March 9, Taibbi testified, with Michael Shellenberger, before the United States House Committee on the Judiciary Select Subcommittee on the Weaponization of the Federal Government in a hearing on the Twitter Files.

[107][108] Taibbi received a visit from Internal Revenue Service (IRS) agents the day he testified to Congress about the Twitter Files.

Jim Jordan, chair of the House Judiciary Committee, has demanded that IRS turn over copies of documents related to its search.

[113] During the Munk Debates on November 22, 2022, Taibbi and conservative Douglas Murray successfully argued in favor of the motion "Be it resolved, don't trust Mainstream Media".

"[116] Using the term "Russiagate", Taibbi covered the story around Russian interference in the 2016 United States elections and criticized the mainstream media coverage of the Special Counsel investigation.

"[120] In response to the March 30, 2023 indictment of Donald Trump, Taibbi said, "If presidents think they will be chased into jail under thin pretexts as ex-presidents, they'll try even harder to never leave office.

[116][independent source needed] In 2021, Ross Barkan of New York wrote, "Taibbi is—or was, depending on your view—one of the most celebrated investigative journalists of his generation."

[14] In 2023, Nick Gillespie of Reason wrote that when Taibbi attacked Hillary Clinton "as a sellout, argued that the Russiagate narrative was mostly bullshit, and equated the manipulative tactics of right and left media personalities, progressives gave him the cold shoulder.