The Free Press · October 2026

Crooked Media Co-Founder Jon Lovett Hosts Hasan Piker

• On September 18, Jon Lovett — former Obama speechwriter, host of Lovett or Leave It, and a co-founder of Crooked Media — hosted streamer Hasan Piker, calling him "the star of this year's midterm elections" and "America's sweetheart."
• The report cites Piker's prior statements: that "America deserved 9/11" (Reuters), that he would pick Hamas over Israel "every single time," that the Soviet Union's collapse was among the 20th century's greatest catastrophes (Instagram), and that the U.S. compares unfavorably with Al Qaeda (Axios).
• Lovett told Piker he is "part of a pro-democracy coalition in the fight against fascism," also naming former Republicans, Neera Tanden, Shannon Watts, AOC, and Bernie Sanders as included.
• Anti-gun violence activist Shannon Watts, told of being grouped with Piker, said she is concerned by "the suggestion that, because the stakes are so high, we must overlook rhetoric or behavior we would otherwise reject."
• Democratic podcaster Ravi Gupta said the Crooked team presents itself as casual commentators while making decisions with long-term implications for the Democratic Party, including which candidates they favor.

Episode details and quotes via the original report; Piker's cited statements link Reuters, Instagram, and Axios as shown in the original. Original headline: "The Democratic Party's Crooked Kingmakers".