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 land in bankruptcy court this year, in a rapidly shrinking industry that’s being squeezed out of the U.S. power market by cheaper options such as natural gas, solar and wind power.

The long-anticipated bankruptcy is another sign that President Trump’s efforts to save the sputtering coal industry, a central promise of his 2016 campaign, have largely failed.

It also speaks to the “significant stress on the coal industry today,” said Benjamin Nelson, a coal analyst and Moody’s vice president. Coal once fueled about half of all U.S. electricity; now it powers less than a quarter.

The legal maneuver also could imperil the solvency of a major pension fund that covers tens of thousands of coal miners and has renewed calls for the federal government to step in and help support the retirement payments.

“We’re talking about 82,000 miners who are going to lose their pensions, and we’re fighting this,” Sen. Joe Manchin III (D-W.Va.), whose state is home to large Murray Energy operations, said in a radio interview on West Virginia MetroNews on Tuesday.

St. Clairsville, Ohio-based Murray Energy said it reached a restructuring agreement with its creditors and will run the business 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 will 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. Murray Energy operates more than a dozen mines throughout Ohio, Kentucky, West Virginia, Illinois and Utah and produces 76 million tons of coal annually.

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 on behalf of the coal industry were spurned by independent agencies despite support from Trump and his deputies.

Last year, members of the Federal Energy Regulatory Commission (FERC), including four selected by Trump, unanimously rejected a proposal from Energy Secretary Rick Perry that would have given subsidies to coal and nuclear plants that Perry said would ensure reliability in the electric grid. But the plan was widely seen as a way of propping up ailing power stations.

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 the FERC as “feckless” for failing to protect coal plants and said he is “extremely disappointed” in the TVA’s decision.

But he reserved his sharpest criticism for Obama, whom he once called “the greatest enemy I’ve ever had in my life,” over regulations he saw as destructive to the industry.

Yet rolling back Obama-era regulations may provide just a modest boost to the coal industry. Researchers at Columbia University found in a 2017 study that the four biggest rules enacted by the Obama administration on coal-mining firms and coal-fired power plants accounted for only about a 3.5 percent decline in U.S. production. Instead, the downturn was mostly due to lower demand for U.S. coal at home and abroad, especially in China.

“Coal’s decline in the U.S. is driven by market forces, notably cheap gas and renewables, not by policy,” said Jason Bordoff, founding director of Columbia University’s Center on Global Energy Policy and co-author of the study.

While three of Murray Energy’s rivals — Alpha Natural Resources, Arch Coal and Peabody Energy — trimmed debt and shed unprofitable assets during their bankruptcy proceedings in 2015 and 2016, Murray was scooping up mines in West Virginia and Illinois.

The spending spree helped saddle the company with about $2.7 billion in funded debt, as well about $8 billion in actual or potential obligations to fund pension and benefit plans, according to court filings.

“That’s a very heavy interest payment, and in a declining coal environment, that creates cash flow problems,” said Vania Dimova, an associate director at S&P Global.

The bankruptcy filing also put the United Mine Workers of America’s already fragile pension plan on even shakier ground. Murray Energy counts billions in payments into the plan, as well as other employee benefits, among its liabilities.

“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.

If Murray Energy is able to shed its pension obligations through bankruptcy, as many other coal companies have done, the fund will be insolvent by 2020, said Manchin, who is pushing for legislation to transfer certain federal funds into the pension plan. The money was previously projected to dry up by 2022.

That legislation has gained little traction in the GOP-controlled Senate. Despite being from the coal-producing state of Kentucky, Senate Majority Leader Mitch McConnell (R) is “still sitting on it,” Manchin said.

McConnell met with UMWA members from Kentucky earlier this year and shares their concerns about the potential insolvency, according to McConnell spokesman Robert Steurer. While his office added that McConnell “supports the ongoing process to find a bipartisan solution for pension reform,” he did not commit to bringing any particular legislation to the floor.

Moore, the company’s new CEO, hinted in a court filing that Murray Energy may seek relief from its pension obligations.

“Murray’s employees are its lifeblood. Nonetheless, the cost of servicing its funded debt, together with the myriad of obligations Murray has to current and former employees, including to a pension fund that has been abandoned by other employers, have substantially reduced liquidity,” Moore told the U.S. Bankruptcy Court for the Southern District of Ohio.