Joshua Friedman’s endurance carries through to the way he and his partner, Mitchell Julis, run Los Angeles-based Canyon Partners LLC, the $19 billion hedge fund. The two debt investors founded Canyon in 1990 and have built it into the 9th-most-profitable fund and the 17th-largest firm in the world, according to Bloomberg Markets magazine’s annual hedge-fund ranking in the February issue.

A smaller part of Canyon’s operation -- real-estate lending and investing -- has stirred controversy. The firm has tangled in court with developers from New York to Nashville to Los Angeles who have defaulted on its loans. Canyon’s real estate funds often end up taking control of the underlying real estate or the assets they financed.

It now runs an ailing casino hotel on the north shore of Lake Tahoe once owned by Frank Sinatra. One of the firm’s opponents in court has called it a “vulture” and said it charges interest rates as high as 27.7 percent that border on usury. A Canyon spokesman says the lawsuits are the exception. Few of the firm’s 240 commercial real-estate investments have ended up in court, and 94 percent of its loans have been paid back under the agreed-upon terms, the spokesman says.

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