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The Trump administration has spent three years trying to help the coal industry by rolling back environmental regulations and pushing for subsidies for coal-fired power plants. Still, the long list of coal company bankruptcies has continued, and dozens more plants have announced their retirement since President Trump took office.

Now the list of bankruptcies includes a company headed by one of Trump's most vocal supporters. Murray Energy Corp. filed for Chapter 11 on Tuesday morning.

The company says it reached an agreement to restructure and continue operating. As part of that, Bob Murray — the chairman, president and CEO — will relinquish two of his roles. His nephew, Robert Moore, will become president and CEO while Murray will stay on as chairman.

"When you're a private company and you're in financial failure, the first person that loses everything is the owner. And that's what will happen," Murray tells NPR.

Murray has had a close relationship with the Trump administration. He donated $300,000 to Trump's inauguration and has met with administration officials to advance the coal industry's interests.

At Murray's headquarters in St. Clairsville, Ohio, there's a photo in the lobby of Murray with President Trump, who's giving two thumbs-up. And in Murray's big corner office there's a replica of Air Force Two, signed on the wing by Vice President Pence.

A few months after Trump was sworn in, Murray met with Energy Secretary Rick Perry and delivered an "action plan" for helping coal. It included 16 proposals that became a "to-do list" for the Trump administration, including replacing former President Obama's Clean Power Plan and withdrawing from the Paris Agreement.

But the Trump administration hasn't been able to give Murray everything he wants. Earlier this year the Tennessee Valley Authority voted to close a large coal-fired power plant that bought coal from Murray, despite pressure from Trump to keep it open. And last year the Federal Energy Regulatory Commission rejected a proposal to subsidize coal and nuclear plants that Murray supported.