Ravi Gupta unpacks a volatile primary season, where ideological insurgents are gaining ground, independents are being sidelined, and both parties’ youngest voters appear increasingly drawn to political extremes. He also examines Alaska’s surprising electoral possibilities and a radically reshaped Democratic presidential calendar designed to test candidates across a broader coalition. Then, acclaimed novelist and former PEN America president Dinaw Mengestu explains why he resigned over the organization’s approach to Israel, Gaza, and the boycott movement. Their probing conversation confronts a defining free-speech question: When does a boycott constitute legitimate political expression—and when does it become discrimination?

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