Dreamland Conversations: The 2026 Midterms – A Look Ahead

With control of Congress on the line, the 2026 midterms will test everything both parties think they know about the American voter.

Dreamland Conversations brings two of Washington’s most seasoned political strategists — one from each side of the aisle — to the Nantucket stage for a candid look at what’s coming in November.

John McCarthy, former Senior Advisor for Political Engagement to President Joe Biden and now a principal at Causeway Strategy Group, and David Urban, CNN senior political commentator and the senior adviser widely credited with Donald Trump’s 2016 Pennsylvania strategy, have spent their careers in the rooms where campaigns are actually won and lost. They don’t agree on much. That’s the point.

Moderating is Kristen Holmes, CNN’s Senior White House Correspondent, who covers the Trump White House daily and traveled with the campaign through the 2024 cycle. She’ll press both sides on the races that matter, the coalitions in play, the money moving through them, and what a divided or unified Washington would mean for the two years that follow.

Expect a substantive, unvarnished exchange rather than a night of talking points — the kind of conversation that has made this series a cornerstone of the Dreamland’s year-round programming. Audience Q&A to follow.