What’s more, the tax Happy I’ll Be Home For Christmas Shirt records show that Mr. Trump has once again done what he says he regrets, looking back on his early 1990 meltdown: personally guaranteed hundreds of millions of dollars in loans, a decision that led his lenders to threaten to force him into personal bankruptcy. This time around, he is personally responsible for loans and other debts totaling $421 million, with most of it coming due within four years. Should he win re-election? There is, however, a tax benefit for Mr. Trump. While business owners can use losses to avoid taxes, they can do so only up to the amount invested in the business. But by taking personal responsibility for that $421 million in debt, Mr. Trump would be able to declare that amount in losses in future years.
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The balances on those Happy I’ll Be Home For Christmas Shirts loans had not been paid down by the end of 2018. And the businesses carrying the bulk of the debt — the golf resort ($125 million) and the Washington hotel ($160 million) — are struggling, which could make it difficult to find a lender willing to refinance it. The broader economy promises little relief. Across the country, brick-and-mortar stores are in decline, and they have been very important to Trump Tower, which has in turn been very important to Mr. Trump. Nike, which rented the space for its flagship store in a building attached to Trump Tower and had paid $195.1 million, left in 2018.