The Trump Organization, run by sons Eric and Don Jr., was struggling with the devastating consequences of the Covid-19 pandemic even before their father incited a raid on Congress. Efforts to sell his Washington hotel were shelved, his office buildings were losing value amid a glut of space in Manhattan, and his golf courses were facing the reality that younger generations aren’t so interested.

Trump entered office worth $3 billion. Despite soaring stock prices and his own tax cuts, he will leave about $500 million poorer, according to the Bloomberg Billionaires Index.

His buildings are saddled with more than $1 billion in debt, most of it coming due in the next three years and more than a third of it personally guaranteed. Refinancing would mean finding lenders and corporations willing to work with history’s only twice-impeached ex-president.

“Nothing like this has ever happened to him,” said Barbara Res, who was an executive in Trump’s company for years. “Will he come back? My gut tells me yes, because he always comes back. But he won’t come back the same.”