Chapter 5.4 | Lawfare, Authoritarianism and the consequences of division

What Trump’s executive orders against law firms reveal about him, about us—and about the unraveling of institutional trust on both sides

As Red Lines Are Crossed—We Are Reaping What We Sowed

Over the past few weeks, Donald Trump’s executive orders targeting prominent law firms—allegedly for their partisan affiliations and past involvement in legal action against him—have rightly triggered a constitutional firestorm.

Are you really surprised? You shouldn’t be.

Trump told us what he was going to do if re-elected. He didn’t hide it. The playbook was printed, promoted, and mailed to donors. If anything, the more honest question to ask is: why did we let the system get so corrupted that this kind of retaliation feels inevitable?

This isn’t just about Trump. It’s about the long arc of a system that abandoned common sense and fairness in favor of ideological purity and winner-takes-all partisanship.

The same system that once celebrated lawfare as a legitimate tool to discredit its political opponent, now recoils as that strategy comes home—only this time, wielded as a more blunt and dangerous instrument. This isn’t just tit for tat. It’s escalation. One side provokes, the other responds with more force. Legal challenges become executive orders. Influence becomes coercion. What began as asymmetric skirmishes in courtrooms is turning into a full-scale institutional arms race, where each side justifies its excesses as payback for the other’s. The result isn’t justice—it’s a system tearing itself apart under the illusion of accountability.

We are not just witnessing the erosion of guardrails—we are watching the logical outcome of a system that mistook extremism for moral clarity, and weaponization for justice. If Trump is crossing red lines now, it’s worth asking who blurred the lines—and who erased them when it served their side.

The Executive Order and Its Fallout

In early 2025, President Trump signed executive orders effectively blacklisting several high-profile law firms. One of them—Perkins Coie—was barred from federal buildings, lost government contracts, and had its attorneys stripped of security clearances. Others were told to abandon DEI programs or provide pro bono legal services aligned with Trump administration priorities.

The backlash was swift. Lawsuits were filed. One federal judge struck the order down as unconstitutional retaliation. Critics called it mob-style retribution. Supporters called it accountability for a legal establishment they believe has long played kingmaker behind the scenes.

But in this moment, the outrage—real as it may be—feels hollow. For years, both parties have danced dangerously close to this line, undermining institutions while claiming to defend them. If this feels like escalation, that’s because it is. But escalation is always a response—and often, a predictable one.

The Lawfare Precedent

What Trump has done with executive orders may be new in form, but not in spirit. For the last several years, the political and legal apparatus aligned with the Democratic Party has engaged in what many call “lawfare”—using investigations, lawsuits, and criminal charges to corner political adversaries in courtrooms they can’t win at the ballot box.

Was all of it unjustified? No. I recall a conversation with a Trump supporter who was complaining that the Biden Administration was using lawfare against Trump. I confronted him and said “if you’ll admit Trump committed the crimes, I’ll happily admit that the Biden Administration has crossed the line on lawfare”. Of course, he refused.

Prosecutors, AGs, and well-funded legal groups affiliated with the left aggressively pursued Trump and his allies. Multiple indictments. Coordinated press leaks. Civil suits with campaign-season timing. It was intentional and the result is clear: to many Americans, the legal system no longer was impartial.

So the pendulum swings and everyone is shocked when it crashes through the clock. Trump’s retaliation isn’t the start of something. It’s the response to something. And that’s what makes this moment so dangerous: both sides now believe they are justified in breaking norms—because the other side broke them first.

When Resistance Becomes Fuel

This moment reminds me of a line from Stephen Mitchell’s 1988 interpretation of the Tao Te Ching:

Give evil nothing to oppose and it will disappear by itself.

The Tao suggests that resisting what you hate with too much force can give it power. And here in America, that dynamic is on full display. In trying to destroy Trump, the left has unwittingly helped define him—as a folk hero to millions who saw not a tyrant, but a target. Not a villain, but their messenger.

Aristotle, in Poetics, offers a similar insight. Tragedy isn’t driven by good versus evil. It’s driven by choices—flawed, often well-intentioned—that spiral toward consequences no one wanted. That’s where we are. Not in a morality play, but in a political tragedy.

The villains in this story are less people and more patterns. Hubris. Retribution. Institutional decay. And the refusal, on all sides, to break the cycle before it breaks us.

A Tale of Two Playbooks

Critics say Trump’s executive orders are part of the Project 2025 agenda—a blueprint for transforming the federal government into an instrument of partisan loyalty. They’re not wrong to worry. The plan consolidates power, purges civil servants, and bends institutions toward the will of the executive.

But here’s the uncomfortable truth: the left has long used its own version of this playbook—just more quietly.

Biden’s White House pressured social platforms to suppress dissenting COVID or election-related speech. The Disinformation Governance Board was a real thing. And Missouri v. Biden revealed just how deeply entangled federal agencies had become in moderating what Americans are allowed to say.

So yes, Trump’s methods are aggressive. But the logic isn’t new. He’s just playing the same institutional game with different objectives—and fewer filters.

The left institutionalized control through soft power. The right is now trying to reclaim it through hard power. Both are eroding the middle ground. And neither seems willing to stop.

Constitutional Crossroads: Executive Power and the Rule of Law

Judge Beryl Howell called Trump’s actions:

retaliation and viewpoint discrimination - a direct affront to the First and Fifth Amendments.

And she’s right. We should never allow any president to punish lawyers for who they represent. That’s how democracies lose their brakes.

But we must also confront the uncomfortable fact that the presidency does carry sweeping powers. The Constitution grants the executive wide authority over national security, federal contracts, and access to classified spaces. And as DOJ official Richard Lawson argued in court:

We are not retaliating for political speech—we are protecting the integrity of federal operations from coordinated legal sabotage.

This isn’t a defense of the orders. It’s a recognition that the Constitution doesn’t enforce itself. It must be interpreted and upheld by people with wisdom, restraint, and a commitment to fairness. And those qualities, tragically, are in short supply on both sides of the aisle.

We Must Change How We React to Trump

When a friend compared Trump’s second-term agenda to authoritarian regimes, I didn’t disagree. The warning signs are real. The rhetoric is dangerous. The consolidation of power should alarm us.

But Trump hasn’t eliminated elections. He hasn’t jailed journalists. In 2020, the system worked. The courts held. Congress certified. Power transferred. That matters.

The question now isn’t whether Trump might cross red lines. It’s whether the rest of us are capable of seeing how our own reactions have brought us to the line in the first place.

At the heart of this essay is a plea: that we change how we react—not just to Trump, but to the system itself. The instinct to fight fire with fire has only made the blaze worse. It’s time for vigilance, not vengeance. Wisdom, not warfare.

In the end, who we elect matters. We’ve allowed the political duopoly to rig the system and that has brought us to the brink.

Let’s not feed fire with fire. Let’s protect the Constitution by staying rooted in it—even when we’re most tempted to weaponize it.