When Jay Sugarman’s IStar Financial Inc. bought Fremont General Corp.’s commercial lending business in June 2007, the deal brought loans on undeveloped residential land as new home sales were two years into a six-year slide.

The $1.9 billion debt-fueled purchase pushed IStar to the brink of default as the financial crisis unfolded. Its shares, which hit an eight-year high of $52.54 that year, plunged 99 percent by February, 2009. From the second quarter of 2011 through the end of last year, IStar reported seven consecutive quarters of net losses as commercial delinquencies piled up.

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