For Mr. Clarke, the Patriot agreement opened the door to other deals. He took over reclamation obligations from Walter Energy, another mining company that had declared bankruptcy. He also picked up more viable mines and a coke processing plant from Walter. This spring, his company vied to take over an entire coal company, Alpha Natural Resources, but the bid was not accepted in the bankruptcy case.

“For someone with zero experience to come into this complex and troubled industry proposing the sort of things he is proposing is astonishing,” said Mr. McGinley, the law professor. “I give him the benefit of the doubt. But I don’t see where it is going.”

‘Coal Isn’t the Villain’

It was raining when Mr. Clarke and a clutch of miners rode a cavernous elevator 734 feet down to the dank shafts of Federal mine No. 2 last spring. At the bottom, the men boarded trains that clanked and jerked along wooden tracks through a maze of silent tunnels, empty except for the occasional mouse scurrying. The trains passed emergency shelters and ventilation shafts pumping cool air from above.

This is the miners’ 45-minute commute to the coal seam, where they shave off thousands of tons of black rock each week.

“I am proud of you,” Mr. Clarke told some of the miners.

As part of the deal with Patriot, the coal miners’ union invested $10 million and took a 20 percent stake in the Federal mine, which Mr. Clarke says he is doing everything he can to keep open even though it doesn’t break even.

When he bought the Federal mine from Patriot, Mr. Clarke said he expected to sell its coal for at least $50 a ton. Recent shipments have sold for just above $40 a ton, he said. On some weeks, the mine has had to operate on a three-day schedule because of the low demand for thermal coal, which is used to produce electric power.

Phil Smith, a spokesman for the United Mine Workers of America, said the union expected production to improve at the mine when the broader coal market recovered.