Reflecting on Trump’s Entry into Politics
It’s hard to believe that it was 11 years ago this week when I predicted to my son that Donald Trump would win. This was long before the escalator moment, the rallies, the investigations, the indictments, impeachments, and all the chaos that would come to define a decade of American politics.
“Washington isn’t prepared,” I told him. “People are so enraged and frustrated, convinced that no one is listening to them—they will send Trump to Washington.”
What I was trying to convey wasn’t a prediction of specific policies; it was an understanding of the prevailing sentiment among the American people.
For years, citizens have listened to politicians from both parties promising action on issues like border security, Iran’s nuclear ambitions, and government waste. Yet each election cycle came and went, but the problems persisted.
Interestingly, while rewatching Moneyball, a line resonated more deeply than much of the political analysis I’d encountered: “The first person to break through the wall usually ends up covered in blood.” It referred to baseball, but it spoke volumes about human nature.
As Red Sox owner John Henry insightsfully noted, Billy Beane’s challenge was not merely about changing business practices. It threatened livelihoods built on those very practices, and such threats rarely provoke calm responses. Often, they incite panic, leading people to act and defend ideas that seemed ridiculous just years prior.
Trump didn’t arrive with groundbreaking information. Rather, he boldly voiced what countless Americans already believed but felt unable to express. Just like in baseball, the statistics were common knowledge—politicians of every stripe had discussed border security, sounded alarms about Iran’s nuclear capabilities, critiqued trade circumstances, lamented government waste, and recognized manufacturing declines. Sure, some articulated these issues more eloquently than Trump. But that wasn’t the crux of the matter.
The debate wasn’t about whether problems existed but rather whether anyone intended to address them. What resonated with many Americans wasn’t a new diagnosis; it was Trump’s promise to act.
This raises an interesting question: if the ideas are not new, why the reaction?
The answer isn’t rooted in policy but in incentives. The founders of America might have understood this instinctively. Influenced by their historical context, they believed that as people gained power, they rarely became less self-serving. Their focus was on the constraints that would limit rulers rather than on their inherent virtues.
Barack Obama termed such restrictions as “negative freedom.” The founders recognized that organizations, much like individuals, have a strong inclination for self-preservation.
Washington excels at discussing issues. Politicians campaign on them, consultants generate funds, advocacy groups form around these challenges, and media outlets build their businesses around them. All these issues can lead to donations, influence, and careers.
Some Americans began to suspect that Washington preferred managing problems over resolving them. Issues sustained donations, influence, elections, and power, while solutions threatened budgets, bureaucracies, and political relevance.
Ultimately, resolving problems might harm the organizations that have formed around them. This doubt about intentions didn’t originate with Trump; he simply highlighted it and, in a sense, shattered the metaphorical fourth wall.
In politics, as in theater, a fourth wall exists that separates the players from the audience. While newspapers and television networks offered commentary, the public passively observed, dominated by a select few institutions. Trump disregarded this barrier, communicating directly with the audience.
He didn’t create distrust. He brought it to the forefront of national conversations, shining light on establishments that had become accustomed to that dynamic. As more individuals recognized that these entities seemed more focused on their own preservation than serving the public, the foundation began to tremble.
Millions adjusted their perspective, noticing the mechanics behind the scenes. They grew skeptical of whether the political performance was as genuine as they had assumed.
The backlash against Trump was neither purely about policy but rather the establishment itself. Ironically, those who previously championed open borders displayed immense energy in defending the institutional walls Trump breached in Washington—a wall steeped in authority and a narrative that went unchallenged.
Whether he exposed flaws within the system or highlighted the disconnect from the populace has become secondary. Once the curtain is pulled back, it’s hard to pretend you didn’t see beyond it.
And that’s why the struggle continues. While Trump remains a focal point, millions have already glimpsed what lies behind the scenes.
The pressing question is: what happens after Trump? Will Americans persist in questioning a system that prioritizes its own protection over fulfilling its mission? Will leaders handle public concerns as genuine responsibilities rather than campaign talking points? Regardless of which party finds itself in power, will people maintain a healthy skepticism toward centralized power?
The first individual to break through a wall often finds themselves covered in blood
The real question now is whether America intends to walk through that opening or spend the next generation rebuilding the barriers that once confined it.
