During my long military intelligence career I spent countless hours with my peers working on diverse “What if … ?” contingency scenarios in complex locales such as the Balkans and Afghanistan. In these intensely personal environments, where clan or tribal loyalty is paramount, local and regional leaders, often with links to organized criminal activities and enabling transnational networks, could be dangerously unpredictable. Judging from the array of personality traits gleaned from these and numerous other experiences, and correlating them to his current circumstances, to me Trump appears to be a classic flight risk.

Setting aside for the moment his conduct as president, Trump faces a financial and legal reckoning of immense proportions as soon as he leaves office. If he loses, he will no longer have protection from an avalanche of charges and lawsuits against him, his family and the Trump Organization. His years of alleged tax evasion will be officially scrutinized—and far more publicly than before he held office. He will no longer be able to claim (falsely) that his taxes are still “under audit” and unavailable. Trump properties and investments could be frozen, seized or plummet in value. The true nature of his extraordinary personal financial debt—recently reported as $421 million—will be exposed, and his likely foreign creditors revealed. Surely adding to his worries was the announcement on October 15 by the Internal Revenue Service that it is indicting Robert Brockman, a wealthy Houston software magnate, in its largest tax-fraud case ever. The action against Brockman shows that the IRS is not afraid to go after big fish who attempt to circumvent their tax obligations.

Personality and longstanding habits are key factors in assessing a subject’s likely future behavior and choices. Even the most casual observer knows that Donald Trump is heavily invested in his self-image as a successful businessman and wheeler-dealer. He takes pride in flouting norms, finding loopholes and playing fast and loose with laws and the truth. If his private financial house of cards is put on harsh public display in high-stakes government and state-level litigation, the aura of celebrity and success that Trump has cultivated for decades is not likely to survive intact. There is nothing in this president’s demeanor, past or present, to suggest that he has the fortitude or integrity to face auditors, prosecutors, or anyone else who challenges him, particularly if the outcome is likely to involve public humiliation and loss of assets, prestige and power. The option of salvaging what he can by relocating to a jurisdiction beyond the reach of U.S. laws would not be a stretch for someone who has long been openly disdainful of our tax and legal systems.

While it is rare among leaders of developed democracies, during the past 50 years we’ve seen a number of high-profile flights by national leaders facing major legal, political or societal problems at home, These include Bolivian president Evo Morales, who fled to Mexico just last year; Ukraine’s Viktor Yanukovych, who fled to Russia in 2014; and Ferdinand Marcos from the Philippines in 1986. All three fled in the wake of contentious elections, either after being ousted by voters or toppled by sustained protests. At the moment nothing suggests that Trump faces the unlikely prospect of being chased out of the country. But it’s no stretch to point out the parallel, either: They were all unorthodox strongman leaders who abused their offices, and simply didn’t see a way to stay comfortably in their countries once they’d lost power.

In the U.S., Trump might be familiar with some of the high-rolling financial fraudsters who decamped from the U.S. as the law was closing in. Among the most notorious was Robert Vesco, who successfully evaded justice by fleeing in a corporate jet in 1973 and remained out of reach until his death decades later. Less fortunate were Richard Allen Stanford, 2009, and Martin Frankel, 1999. Both tried to escape the U.S. by leasing private jets. Stanford was captured before he could finalize arrangements; Frankel made it as far as Germany but was later extradited to the U.S. for a long jail term.

If Trump were to lose the election and opt to slip away, where, when, and how might such a scenario play out? The “where” is straightforward: His most logical move would be to negotiate asylum somewhere from which extradition would be difficult. Doing so would allow him to temporarily escape U.S. jurisdiction and law, although he would also become in essence a hostage, a gilded trophy of sorts. After first fleeing to Costa Rica in 1973, Vesco made his home in Antigua, Nicaragua and Cuba, whose governments were not inclined to cooperate with U.S. authorities. And Edward Snowden, the disgruntled Booz Allen contractor turned whistleblower, has been living in Russia, under the protection (and eye) of the Putin regime, after fleeing the U.S. in 2013 with a treasure trove of classified information.

When and how Trump might exit the country are slightly more complex questions. If Trump is decisively trounced next week, one subset of possibilities emerges; if his defeat is a narrow one, another subset arises.

If Trump loses badly, it is conceivable he could plan a stealth departure sometime during the 11-week period before Inauguration Day, while he still has the protection of legal immunity as a sitting president. Leaving U.S. airspace before he resumes the status of private citizen at noon on January 20 would allow him to escape—or at least delay—dealing face-to-face with many creditors and lawsuits. Classic indicators of preparation for such a move would include fast sales of domestic properties and investments, and a quiet amassing of wealth offshore, out of reach of U.S. authorities. Trump’s family members and trusted corporate staff would likely be heavily involved in orchestrating the relocation.

A chilling alternative, however fanciful, could arise if Trump flees abroad after losing a close, viciously contested election. Hunkered down in a foreign country willing to provide sanctuary, he could conceivably style himself a “president in exile” and incite his die-hard American followers to resist the election results. A degree of domestic upheaval and dangerous division would linger for an extended period until the new administration is able to foster calm and unity.

How might this happen? What methods might a sitting U.S. president use to leave the country on a one-way journey? The choice could be as brazen as not reboarding Air Force One while out of the country at a conference or summit. Cases abound of athletes and artists escaping repressive regimes by refusing to reboard official aircraft and instead negotiating asylum. While on U.S. shores, Trump could find a creative way to slip his Secret Service detail and fly away in a friend’s private jet or foreign aircraft. Sailing away into international waters would also be a plausible option. In 2019, fugitive U.S. computer-security software magnate John McAfee used his yacht to elude the IRS and Securities and Exchange Commission for months until he was arrested in Spain on October 6, 2020. Steve Bannon made news last August when the Coast Guard arrested him while on a foreign yacht off Connecticut.

If all this sounds like a B-grade spy novel, it should. The flight of a U.S. president would be unprecedented, unsettling and profoundly disappointing. As a minimum, a presidential defection would temporarily absorb the resources and attention of a wide range of U.S. defense, intelligence and law enforcement agencies. In more than two centuries of peaceful transfers of presidential power, nothing remotely conceivable like it has ever happened.

I fervently hope we won’t face such a disturbing turn of events. But if there is anything to learn with this president, it is to expect the unexpected. As his unabashed admiration of authoritarian world leaders has shown us these past four chaotic years, Donald Trump values autocrats over democratic government, and places his self-interest well above the sacred trust he was elected to protect and uphold four years ago.