At last year’s Kennedy Center Honors, the venue’s biggest event of the year, Trevor Milton took in part of the show from the balcony where honorees, celebrities and the president and first lady sat. Afterward, the entrepreneur mingled with guests—honorees included Sylvester Stallone and George Strait—inside the SyberJet Lounge, a swanky space that his company had spent millions to sponsor and that President Trump had called “gorgeous.” That the 43-year-old was attending the black tie event with stars and Washington elites in December is a sign of how drastically Milton’s fortunes had changed in 2025. Early that year, Nikola, the…

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