Richard Grenell has made a career of being everywhere at once: ambassador to Germany, intelligence chief, presidential envoy, and acting head of the Kennedy Center. But his jack-of-all-trades status in President Donald Trump’s orbit may be catching up with him.
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According to reports from The New York Times and The Hill, Grenell, who jockeyed for the cabinet position last year, recently undercut Secretary of State Marco Rubio’s high-stakes negotiations with Venezuela, throwing a delicate prisoner swap into chaos and leaving both American hostages and Venezuelan political prisoners in limbo.
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In April, Rubio, the administration’s top diplomat, had been working through official State Department channels to free about a dozen Americans and dozens of Venezuelan political prisoners. In return, the United States would send home roughly 250 Venezuelan migrants it had deported to El Salvador, men the Trump administration claims, without definitive proof, are linked to the Tren de Aragua gang.
Those migrants remain confined in El Salvador’s sprawling CECOT prison, a massive complex widely condemned by human rights advocates. The prison has become notorious in U.S. political debates after the Trump administration deported migrants there, including Andry José Hernández Romero, a gay Venezuelan asylum-seeker who legally entered the United States but vanished into CECOT’s cells.
Hernández Romero, who fled Venezuela after facing persecution for being gay, has not been seen or heard from since he was disappeared to CECOT in March, sparking outrage among LGBTQ+ advocates and lawmakers.
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While Rubio sought to broker a swap, Grenell was quietly pursuing his own deal. Instead of focusing on a direct exchange of prisoners, he offered Venezuelan President Nicolás Maduro a potential economic lifeline: allowing Chevron to keep its oil operations in Venezuela if the regime released American detainees.
Venezuelan officials, caught between conflicting U.S. proposals, balked at the idea. The deal collapsed, leaving detainees stuck in dangerous limbo. “It just says that the administration, part of it doesn’t know what the other’s doing, and that can put Americans at risk,” Maryland Democratic U.S. Sen. Chris Van Hollen told The Hill.
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Grenell has dismissed the Times’ reporting as false. Yet even some conservatives are wary of his freelance diplomacy. Elliott Abrams, Trump’s former special representative for Venezuela, told The Hill, “I think that’s what happens when Grenell goes freelancing. So I think what needs to happen here is to leave foreign affairs in the hands of the State Department … and just get Grenell’s butt out.”
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