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The Message Box

If Trump Is So Unpopular, Why Do His Candidates Keep Winning?

Plus a look the battle for the House post-Supreme Court and whether Dems should intervene in primaries

Dan Pfeiffer's avatar
Dan Pfeiffer
May 23, 2026
∙ Paid

Welcome to this week’s mailbag. So many questions this week, and a lot of them came in on Tuesday night and Wednesday morning after a Trump-backed candidate easily beat Representative Thomas Massie in the Kentucky primary. Folks want to know why Trump-backed candidates keep winning primaries despite Trump being so unpopular. It’s a great question, and I want to get right into it, but first, some housekeeping.

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Karen Quesenberry

So you and other pundits keep telling us how unpopular Trump is, how it’s going to be a backlash, but then in primaries the people he backs keep winning! It feels like his unpopularity isn’t actually showing up in what’s happening on the ground. What do you make of this?

Answer

Look, I get it. I, too, tuned in on the night of the Indiana and Kentucky primaries, hoping for Trump to get his comeuppance, and left disappointed to see him win yet again. Like all of you, I was hoping for a sign that Republicans were ready to truly turn on Trump.

Alas, that was not the case. But Trump-backed candidates winning primaries is not a positive sign for Republicans heading into the fall. In fact, it may portend the opposite.

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