Where the First 100 Days Went Wrong: A New Theory

Why did an agenda that looked unstoppable a few months back run into a brick wall? It has to do tactics meant for insurgents attempting to run the system.

Donald Trump entered his second term at the height of his popularity and powers. The Democrats didn’t just lose the last election, but were humbled. The new administration roared out of the gate with explosive action on multiple fronts—DOGE to uproot the federal bureaucracy, immigration enforcement, explosive foreign policy moves breaking with historic friends in Canada and Europe, a reversal on DEI, a radical new regime of tariffs, and more. Shockingly, Republicans also appeared to be attracting support from new power centers like Silicon Valley, with major figures like Elon Musk, Jeff Bezos, and Mark Zuckerberg showing up at the inauguration. It genuinely looked like Republicans were on the cusp of consolidating power for a generation and completely reorienting America.

100 days later, nearly all those initiatives are under assault. Musk has left Washington, leaving DOGE orphaned. Immigration enforcement is mired in controversial fights over hard-to-justify episodes like deporting people to a Salvadoran gulag. Historic relationships with Europe are shattered for little apparent gain, the world is now suspicious of American aggression, and Canada turned so anti-American it’s boycotting American goods. Tariffs were rolled out haphazardly with frequent unpredictable changes causing market disruptions, global anger, and a trade war that will likely radically jack up prices in a few weeks. The only parts of the agenda that appear to be achieving what Republicans promised were the parts about tearing old systems down—for example, the campaigns against universities and DEI. The parts about building a new version of America are trapped in backtracking and chaos. Trump’s approval ratings have fallen to the low 40s, shedding the middle Americans and independents Republicans picked up from Democrats. Republican-curious powerbrokers from places like Silicon Valley appear to be backing off.

Why did an agenda that looked unstoppable a few months back suddenly run into a brick wall? It’s not Democratic intervention—the Republicans still have full rein to do anything they want. I have a theory that it has to do with tactics and a worldview meant for insurgents and underdogs attempting to run the system.

A STRATEGIC THEORY OF DONALD TRUMP

To understand the last hundred days, we need a fresh strategic profile of Donald Trump. The two most popular ones obviously are wrong. Some have long believed Trump is just an unprincipled idiot, one who got lucky by attaching himself to an ugly social wave. On the other hand, others assert he’s a strategic genius outplaying opponents in a long game of fifth-dimensional chess. In reality, there’s little evidence for either, and his successes and his failures all stem from a unique strategy based around pushing limits without suffering consequences.

It’s difficult at this point to still dismiss Trump as a lucky fool. Even those who hate everything he represents have to reckon with the reality that he’s clearly doing something that consistently works. On its face, it’s ridiculous that a small-time real-estate guy could somehow become a national celebrity, earn a fortune, publish a bestselling book, put his name on countless products, host a highly-rated reality show, and then so completely take over a major political party that it became his personal vehicle. Any single one of those accomplishments should have been impossible. Obviously, there’s some unique and powerful strategy at work that fueled such unprecedented success across multiple domains for over fifty years.

At the same time, there’s little evidence Trump’s successes were the result of careful planning and thinking ten-steps ahead to set up dominoes that would fall perfectly years later. Trump’s management style was never smooth and considered, but chaotic, marred by false starts, backtracking, and memory-holing failure. Throughout his multiple careers as real-estate mogul, celebrity, and politician, he consistently made promises he didn’t keep and pronouncements that didn’t work, later moving on without acknowledging the failures. He alienated people, violated agreements, and famously nearly bankrupted a casino. In his first term as president, he achieved few of his goals—he never built the wall. He left office so unpopular a Democratic Party that struggled to even find a candidate booted him from office, less a win for Democrats than a Republicans loss. Trump is less strategic mastermind than movie protagonist who routinely sets off fiery explosions and somehow walks away unscathed and closer to his goals.

In reality, all of Trump’s successes are the result of an unusual strategy. He pushes limits to discover holes in established systems others will not use, but without suffering the consequences. Over his long career, instead of going into situations and trying to learn how systems work, Trump charged in and began relentlessly pushing on all the walls to see if anything might open. He did this with zero concern for established norms or rules, or recognition of received wisdom about what’s necessary for success or likely to work. He rushes in and tests limits to find openings other people ignore or do not see. Most times, he runs into impenetrable barriers. Every once in a while, an invisible door opens and he races through, getting closer to his goals.

The world, of course, has always had its share of anti-establishment insurgents who exploit existing systems for opportunities. Most succeed for a time until the system notices them and either buys them off to incorporate them, or uses laws and sanctions to take them down. What makes Trump unusual is he seems to have a magic power to understand exactly how far he can push before the system pushes back. By instinct, he presses on walls and doors until one surprisingly opens and he steps through. He then rapidly moves forward waiting to see if the system will push him back. If the system does push back, Trump jumps backwards and pretends nothing happened. If it doesn’t, he continues striding forward toward his goal. He has a talent for understanding just how far he can push things until something bad will happen, and calibrates so nothing ever does. This has allowed him to consistently identify opportunities, pushing systems as far as they will go, but no farther. He finds hidden doors without the system getting organized enough to stop him, exploiting opportunities others fail to see or choose not to pursue. He iterates through failures until he obtains success. This allows him to win any reward he wants.

For decades, Trump used this dance to claim prizes others couldn’t claim, and then danced back before a hammer came down to punish him. He makes deals, and then backs out on commitments he doesn’t want to honor, and often gets away with it. He says things others wouldn’t and, if they turn out to be popular, doubles down. If they don’t, he pretends he never said them or meant them. A lifetime of this dance has rewarded him with incredible personal success. It allowed a minor real estate developer to become an international celebrity, media star, and now the head of a major political party and the president.

As a politician, this same strategy allowed Donald Trump to identify problems the Republican establishment, and then the American establishment, failed to see or wanted to ignore. As he pushed relentlessly on political norms and third rails, Trump revealed neglected issues, national discontent, and opportunities everyone else in politics refused to touch. This catapulted him upward, building a movement of deeply loyal followers, routing the old establishment, and allowing him to humble a Democratic Party that couldn’t see past the old playbook that now was out of date. This strategy, however, was always an insurgent’s strategy based around exploiting a dominant system. That means it only works for insurgents when there’s a dominant system to exploit.

For his entire life and political career, Donald Trump always had a bigger system he was operating inside that he could expertly navigate and exploit. As the American president, however, he is the system. Controlling Congress and the White House, Donald Trump and his Republican Party don’t just represent one faction inside the greater American system. They are the American system. America itself is more than just one country inside the international order. As global hegemon, America is the international order. America set up the Western alliance system it leads, set up the rules of global trade, and maintains the dominant international security arrangements with its military. America is the lynchpin of the global order it created for its benefit. An empire can’t exploit loopholes against itself. The only thing that accomplishes is tearing it’s own power down.

It's a common problem—strategies that get us to the top rarely work once we reach the top. Uber grew quickly as an insurgent by ignoring local taxi regulations and challenging local governments, until Uber became the taxi industry. Then its strategy began to fail, until it found new executives and an establishment strategy for success. Establishment politicians who build careers around climbing ladders face similar problems when they run out of rungs to climb. Presidents like Bill Clinton, who only know how to remain popular, waste years continuing to try to win the office they’ve already won. Our greatest strengths often are our weaknesses. The tools that help us climb the mountain rarely serve us at the top.

WHAT THIS MEANS FOR AMERICA

I suspect the last ten years will be viewed in history not as an era of divided politics but a chaotic era of transition and discovery setting up something else.

The last ten years of Republican politics identified a lot of neglected issues. It exposed places the old system was cracking, and growing resentments among significant segments of Americans we couldn’t continue to ignore. However, the political strategy that identified these opportunities and used them to ride into power was never sufficient to create and implement concrete and thoughtful policies for change. That’s why the strategy that put Republicans into office with so much fanfare looks tattered after only 100 days. This will continue to be a problem until Republicans understand the difference between challenging an empire and running an empire.

However, this is more than just a Republican problem. It’s a political system problem that should concern the Democrats as well. Trump didn’t create the doors he walked through. He succeeded because the system really had hidden cracks to exploit that the establishment ignored. While it’s no longer sufficient to point out neglected problems like an insurgent, it’s also no longer an option to dismiss or ignore them as unwelcome intrusions upon a status quo that already has broken down. Status quo politics from Democrats also will no longer work, dismissing the problems Republicans identified as beneath them, or problems of the enemy, instead of the most powerful problems in America.

Everyone now knows the invisible doors are there. They’ll remain the center of our politics until America develops solutions to fill them. It’s time to transition from rebels as aristocrats into leaders, rebuilding and making the system work.

What do you think about the insurgent strategy? Join the conversation in the comments.