from the article I linked...
Posted on: October 3, 2016 at 11:45:04 CT
zounami MU
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"But in claiming and then recouping that loss through the tax code, experts said, Trump took advantage of the way real estate can be depreciated and interest deducted, even as the value of holdings increases. In that way, future net income can be reduced — in Trump's case, for many years."
He recouped a significant amount of the loss primarily through NOL carryback/carryforward. As Trump has said, this was a smart thing to do. Essentially, the losses were not his, they were Uncle Sam's.