Jeffrey Prosser, who runs the phone company in the U.S. Virgin Islands and is one of the territory’s most influential businessmen, is facing a legal challenge that just a few years ago would have seemed almost unimaginable: an involuntary bankruptcy filing.

New York investment firm Greenlight Capital LLC filed involuntary petitions against Prosser and two corporate entities in Delaware on Friday, seeking payments on some $130 million it is owed in other legal judgments. The Chapter 11 petitions are part of a larger tangle of litigation that includes a suit filed by Innovative’s lender, the Rural Telephone Finance Cooperative, over a $500 million loan.

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