When President Trump leaves the White House in January, he will face some of the deepest financial and legal challenges in his family business empire in decades.

No matter what he focuses on after the presidency, the businesses will require his attention. Two New York investigations will continue after he leaves office and the Trump Organization will need to avert a potential cash crunch caused by looming debt maturities at the firm’s real estate holdings. Personal guarantees Mr. Trump made on some of the organization’s debt...

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