Murray Energy Corp., the private coal giant whose founder pushed the Trump administration for an overhaul of what it called “anti-coal” environmental policy, filed for Chapter 11 protection on Tuesday.

It’s the fifth coal company to head to bankruptcy court this year, in a rapidly shrinking industry that’s being pushed out of the U.S. power market by cheaper and greener energy options as natural gas and renewables. And though restoring coal has been one of President Trump’s central promises since his first campaign, his administration’s efforts to that end have largely failed. Coal once fueled about half of all U.S. electricity; now it powers less than a quarter.

The bankruptcy filing "is another sign of the significant stress on the coal industry today,” said Benjamin Nelson, a coal analyst and Moody’s vice president. Though demand has been declining for about a decade, strong export prices generated solid cash flows in 2017 and 2018, he said. But prices dropped sharply this year, exposing the “poor underlying demand” in the domestic market.

The St. Clairsville, Ohio-based Murray Energy said it reached a restructuring agreement with its creditors and will finance its operations with cash on hand and $350 million in new financing. Robert Murray, who founded the company with a single Ohio mine in 1988, will step down as chief executive and become chairman of the board. He’ll be replaced by Robert Moore, the president and chief executive of Foresight Energy, a Murray Energy subsidiary that is not part of the bankruptcy proceedings.

Murray, who started working in coal mines at 16 to support his family, has long been a Trump ally, donating generously to his campaign and hosting a fundraiser in West Virginia this summer. In 2017, Murray met with White House energy officials to offer an “action plan” calling for deep cuts in the Environmental Protection Agency’s staff, withdrawal from the Paris Climate Agreement, a rollback of safety and pollution regulations and the repeal of President Barack Obama’s Clean Power Plan.

Within a year, the administration followed through by pledging to withdraw from the Paris accord, delivering cuts at the EPA and beginning to repeal and replace the Obama-era plan to curb climate-warming emissions from coal-fired power plants.

Yet at other times, Murray’s efforts to have the federal government throw a lifeline to the coal industry were spurned by independent agencies despite support from Trump and his deputies.

Last year, regulators on the Federal Energy Regulatory Commission, including four selected by Trump, unanimously rejected a proposal from Energy Secretary Rick Perry that was widely seen as a way of propping up ailing coal and nuclear plants.

And in February, Trump tried to intervene with the Tennessee Valley Authority to keep open two coal plants that bought most of their coal from Murray. But the independent agency defied Trump and voted to close the plants anyway.

The always outspoken Murray has blasted FERC as “feckless” for failing to protect coal plants and said he is “extremely disappointed" in the TVA’s decision.

But Murray reserved his sharpest criticism for Obama, who he once called “the greatest enemy I’ve ever had in my life” for issuing regulations he saw as destructive to the industry in which he had spent his entire working life.

Murray Energy operates more than a dozen mines throughout Ohio, Kentucky, West Virginia, Illinois and Utah and produced 76 million tons of coal annually. It employs 7,000 people, according to its website, and counts billions in unfunded retirement benefits and workers’ compensation among its liabilities, the Wall Street Journal reported.

“Now comes the part where workers and their families pay the price for corporate decision-making and governmental actions,” the United Mine Workers of America, which represents a large chunk of Murray Energy’s full time employees, said in a statement Tuesday. “Murray will file a motion in bankruptcy court to throw out its collective bargaining agreement with the union. It will seek to be relieved of its obligations to retirees, their dependents and widows. We have seen this sad act too many times before.”