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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. The balances on those loans had not been paid down by the end of 2018. And the businesses carrying the bulk of the debt — the Doral 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.

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