For most candidates, losing a presidential election is a major setback, but for Donald Trumpthe issues are particularly personal and serious.

As November 5 approaches, Trump’s future hangs in the balance, with the potential consequences of a return to the presidency or serious legal repercussions, including possible prison time.

If he wins, he will become the first president with a criminal record to take office, controlling not only the highest executive power but also access to nuclear codes. However, a loss could result in more lawsuits and possibly even jail time.

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Trump historian and biographer Gwenda Blair explained to the Guardian how Trump has long crafted a public image of invincibility. “He presented himself as the guy who’s doing well,” Blair said, adding, “He’s facing a lot of moments of reckoning. He could go to jail. He could end up considerably less wealthy than he is.” No matter what happens, whether he wins or loses, his health will be tested. Death, ill health, dementia – these are things that even he cannot escape. .”

Over the decades, Trump has often tested legal and ethical boundaries.

In the 1970s, he and his father were sued by the Justice Department for alleged racial discrimination in the rental of their apartments against black applicants.

Later, in the 1990s and early 2000s, several of Trump’s casinos and real estate projects, including Trump Plaza and the Taj Mahal, ran into financial difficulties and filed for bankruptcy, testing his reputation as an entrepreneur. successful businessman.

Legal challenges continued into the 2000s with Trump University, a real estate education company sued for alleged fraud and false advertising. In 2016, he settled the case for $25 million without admitting any wrongdoing.

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Yet as the nation heads to the polls, the possibility of losing looms, not only politically but also personally for Trump. A victory would give him another chance to shape American policy, while a defeat could subject him to legal challenges that could ultimately hold him accountable for his past actions.

Come November, the results of this election could define the limits of his enduring belief that he can surely “get away with it.”