Trump’s May Tests: Indiana State Senate Races and Thomas Massie’s Kentucky Primary

Republican primaries in May 2026 in Indiana and Kentucky are being watched as measures of former President Donald Trump’s sway over the party. In Indiana, Trump-aligned groups have allocated at least $8 million for television, digital, and direct-mail ads supporting state Senate candidates. In Kentucky’s 4th congressional district, former Rep. Thomas Massie faces a primary where Trump’s 2020 endorsement and a prior tweet urging his expulsion from the GOP remain salient.

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Trump has repeatedly leveraged personal funds and a national network of allies to shape GOP nominations, favoring candidates he deems reliable victors. Massie’s most notable congressional action occurred in March 2020, when he blocked a broadly supported COVID-19 relief bill and forced a recorded vote, prompting Trump to tweet that the GOP should expel him. After Massie secured a decisive primary win that month, Trump publicly endorsed him, reinforcing the former’s alignment with Trump’s preferred Republican profile.

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The Indiana effort includes $8 million for television ads and additional, undisclosed sums for digital and mail outreach targeting the state’s older Republican electorate. In Kentucky, Massie captured roughly 75 % of the Republican primary vote, a margin cited as evidence of his strong backing among party members and his compatibility with Trump’s endorsement strategy.

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Trump’s reaction to Massie’s 2020 procedural move was a tweet urging the party to remove him, reflecting direct criticism of intra-party dissent. The same period saw Trump issue a public endorsement of Massie, framing the former congressman as a guaranteed Republican winner. Analysts cited in the source argue that these actions stem from personal ego rather than a strategic effort to shape the GOP’s future direction.

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• “The unnecessary move so angered Trump that he tweeted the GOP should kick him out of the party.” — Donald Trump, former President (tweet, March 2020)

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• “As I wrote years ago, Massie’s most infamous moment "came in March 2020, during those first chaotic weeks of the pandemic, when he refused to allow members to pass a COVID-19 relief spending bill that had broad support without first pushing for a recorded vote on where every member stood.” — Time editorial staff

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• “) This isn’t about Trump’s primacy; it’s about his ego.” — Time editorial staff

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• “Trump and his allies are all-in with Indiana: $8 million and counting on TV ads, plus millions more in digital and mail—yes, mail still works with Indiana’s older GOP base.” — Time editorial staff

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The Indiana state Senate primaries and Kentucky’s 4th-district Republican primary are scheduled for May 2026. Results will indicate whether Trump’s financial backing and public endorsements continue to translate into electoral victories, shaping the GOP’s candidate selection ahead of the 2026 midterm elections.

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