Waterloo

Napoleon was indeed a dictator, though he came to power during a period of political chaos and initially enjoyed significant popular support. Sound familiar? Napoleon seized power through the coup of 18 Brumaire in 1799, overthrowing the Directory government (a lot like the January 6 insurrection attempt). He quickly consolidated authority. By 1802, he became Consul for Life, and in 1804, he crowned himself Emperor of the French (Trump probably has his playbook on his nightstand next to Mein Kampf). Napoleon established all the hallmarks of dictatorial rule: He created an extensive surveillance network to monitor and suppress opposition (think ICE and Hegseth). Newspapers and publications were heavily controlled; only government-approved content could be published (CBS has caved and Trump is attacking NBC and ABC and threatening their FCC licenses). Political opposition was effectively eliminated (redistricting in Texas). He concentrated executive, legislative, and judicial power in his hands. Freedom of speech, assembly, and press were severely restricted.

But Napoleon’s dictatorship had some unique characteristics that distinguished it from many traditional totalitarian regimes. He genuinely commanded widespread support, especially after bringing stability following the chaos of the French Revolution. His government promoted based on talent rather than birth, which was revolutionary for the time (Trump fell asleep before this chapter). The Napoleonic Code became a model for legal systems worldwide and enshrined important principles like equality before the law (not sure Trump has read this chapter yet). His reforms created more effective government institutions (DOGE?). Napoleon regularly held plebiscites (popular votes) to legitimize his power, though these weren’t free elections in the modern sense. The results showed overwhelming support, though coercion and limited choices made them somewhat meaningless as measures of genuine consent. So while Napoleon was undoubtedly a dictator who suppressed political freedoms and concentrated power, he was also a popular leader who brought order and reform. His dictatorship emerged from and initially served the goals of the French Revolution, even as it ultimately betrayed many of its democratic ideals (oops, did Trump say he would not attack Medicare?)

Napoleon’s major strategic blunders began with the disastrous Russian campaign of 1812. His invasion of Russia ended in catastrophic retreat, with harsh winter conditions and Russian tactics decimating his Grande Armée. This massive loss of experienced troops and resources fatally weakened his position (Trump is losing to Putin as I write this). The failed Russian campaign emboldened European powers to form the Sixth Coalition against him. After his defeat at the Battle of Leipzig in 1813, Napoleon was forced to abdicate and was exiled to Elba in 1814 (I hear Elba is a lot like Mar-a-Lago). Napoleon’s escape from Elba in March 1815 began his “Hundred Days” – his final attempt to regain power. However, he faced overwhelming odds: most of Europe had united against him, his resources were limited, and he had to act quickly before enemy armies could fully mobilize.

Napoleon’s downfall was the result of several interconnected failures that culminated in his defeat at the Battle of Waterloo on June 18, 1815. At Waterloo itself, several tactical and strategic errors sealed Napoleon’s fate. Heavy rains the night before made the ground muddy, forcing Napoleon to delay his attack until late morning, giving Prussian forces time to arrive (I hear it rains a lot in Chicago). He sent a significant portion of his army to prevent Prussian forces from joining Wellington, weakening his main attack (LA, DC….its a lot). He dismissed the Duke of Wellington’s defensive capabilities and the strength of the Anglo-Allied position (just like Trump is underestimating Newsom, Powell and Pritzker). His attacks were poorly timed and lacked the coordination that had marked his earlier victories (Trump is losing it cognitively). Blücher’s Prussian army arrived at the crucial moment, turning the tide decisively against Napoleon (watch your flank, Donald, Putin may be done with you and you are all out of allies…even South Korea now…).

The defeat at Waterloo ended Napoleon’s political career permanently. He was exiled to the remote island of Saint Helena (even more like Palm Beach Island), where he died in 1821. His failure stemmed from overextension, the coalition of enemies he created through his conquests, and ultimately his inability to adapt to changing military and political circumstances. Every dictator more or less ends up in the same place, both physically and in history.

In case you haven’t figured it out yet, I’m feeling like Trump‘s planned attack on Chicago may well be, to mix metaphors, a bridge too far. There comes a point in the history of dictators when their power goes to their head and they think they can get away with anything. Many of us who feel we know Trump and have watched Trump for years have been amazed that he has avoided his comeuppance all this time. With the crime levels far worse in the American cities under Republican leadership, it is all too obvious even to the most simple-minded Americans that what Trump is doing in Los Angeles, Washington DC, and now Chicago is a blatant move to attack the centers of his opposition. Every move Trump makes these days is a clear and blatant political move to try and ensure that he will not face a third impeachment after the midterm elections next year. He knows he has taken enough actions that any legal scholar would consider at least impeachable and therefore, he knows that a Democrat controlled House of Representatives will be coming at him with both barrels in January 2027. Like all dictators, Trump is nothing, if not forward-looking with regard to his own potential moment of demise. In fact, dictators tend to spend the ends of their political careers, focused entirely on self preservation.

The game plan is all too clear. The Trump immigration policies have run their course and are now more disliked than approved of by the general population. His tariff policies have created nothing but chaos and are a joke to everyone in the global business community. The TACO trade says it all. Bombing Iran gave him a moment of glory, but that has faded and ended up being a non-event. The situation in Gaza and the blatant starvation and attempted genocide of 2 million people has ceased to be something any thinking person will support. His repeated false promises about ending the war in Ukraine have become an embarrassment to him. For the last several months, he has been under attack, even by his own stalwarts, about the Epstein files. So now he has turned our military establishment into a vehicle, turned inward on its own people, or at least anyone in America who is not cheering him on. His secret police force has become so goon-like that they choose to wear masks to protect themselves from the eventual reprisals they know will come once America reclaims itself from this nightmare. Kristi Noem is forced to offer $50,000 sign-up bonuses to recruit incremental ICE officers. That is telling.

Sooner or later, every dictator goes one step too far. It’s often hard to predict when that moment will arrive. It’s difficult because it has to do with popular disapproval getting to the point where the acolytes surrounding the dictator begin to worry more about themselves than about their fearless leader and what he might do to them if they defect. I’ve not been very good at predicting Trump‘s demise. I freely admit that I have underestimated him for a long time. But I do consider myself a student of modern revolution, and I do believe that every dictator eventually meets his Waterloo. Governor Pritzker does not have that mean and hungry look of Lord Wellington (though he does have his pedigree and inherited wealth), but there is something fitting about one billionaire standing up against the billionaire elite in power. So I’m wondering aloud whether Chicago will be Trump‘s Waterloo. I bet Trump hears ABBA’s words in his ear…”Finally facing my Waterloo…”