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One of the biggest movers of Native American-made cigarettes has filed for federal bankruptcy protection, a month after a court said the wholesaler is responsible for potentially tens of millions of dollars in federal tobacco assessments. The Chapter 11 reorganization filing by Arthur Montour, owner of Native Wholesale Supply on the Seneca Indian Nation’s Cattaraugus Reservation, lists more than $50 million in liabilities by the businessman who has become wealthy by moving billions of cigarettes made on an Ontario reservation to other tribes across the United States.

The company and its Ontario cigarette partners, the subjects of a 2009 investigation by The Buffalo News, also listed as creditors a half-dozen states that have brought various lawsuits against Native Wholesale Supply over its tobacco-distribution practices. But Montour’s biggest creditor — at $43 million — is the U. S. Department of Agriculture, which brought his company to court for failing to pay into a federal trust fund designed to move tobacco growers away from a regulated price market and into a free-market system.

In October, U. S. District Judge Richard J. Arcara ordered Montour’s company to comply with the terms of the Fair and Equitable Tobacco Reform Act of 2004 and pay into the tobacco trust fund. In his company’s Chapter 11 filing with the U. S. Bankruptcy Court in the Western District of New York, Montour listed the $43 million owed to the Agriculture Department as an unsecured claim. Montour acts as a wholesaler of cigarettes — chiefly the Seneca brand—made by Grand River Enterprises, a plant on the Six Nations of the Grand River Indian Reservation in Ohsweken, Ont., near Hamilton.

The cigarettes cross the border near Buffalo and head to various warehouses, including a duty-free zone in Las Vegas, before being sold to tribes across the country. They, in turn, sell the cigarettes tax-free. The cigarettes also are sold by Indian retailers in New York, including most Seneca Nation merchants. Montour, a former Seneca Tribal Council member, had his Perrysburg company incorporated by the Sac and Fox Nation in Oklahoma. Several states have sued Montour’s company for various reasons, including alleged violation of cigarette- shipment laws and sale of cigarettes that do not meet fire-safety standards.

“The [bankruptcy] filing automatically stayed our case against Native Wholesale Supply,” said Diane Clay, Oklahoma Attorney General’s Office spokeswoman. Oklahoma went after Montour’s company in court, alleging that he failed to make required payments into an escrow account created in the wake of a landmark 1998 settlement by 49 states and the nation’s major tobacco companies.