Trump Just Accidentally Revealed His Biggest Weakness

The “strongman” mask slipped for a moment—and once voters see the panic underneath, Republicans have a massive problem.

May 25, 2026

Cliff’s Note: Longtime friend and founder Worth Knowing, Matt Robison, originally published this piece at his Substack. We’re re-publishing it at BAM with his permission.

And Happy Memorial Day! Thank you to all those who served based on the basic democratic belief there are some things bigger than all of us.

The thinking behind President Donald Trump’s $1.776 billion legal settlement fund—which he claims is to compensate victims of political “weaponization and lawfare”—is both crystal clear and deeply mysterious.

Clear in that it’s one of the most naked acts of political corruption in American history: a convicted felon thieving two billion of our tax dollars to shower on a hand-selected cadre of other felons, traitors, and kooks with nothing other to recommend them than fealty.

Mysterious because it was such an immediate and foreseeable debacle. The flaws in the original lawsuit that led to the fund were obvious, the widespread bipartisan outrage over the idea was predictable.

So there’s the enigma: what was the plan here? What was he really after?

After years of writing about Trump and based on my experience in government, I see three real possibilities: an obvious explanation; a souped-up second possibility that’s more cynical (and hence maybe more likely); and a third, more sinister, and yet more tantalizing explanation—one that would give some valuable insight into what, with good reason, Trump fears most.

Theory One: This is Trump

Since this is, after all, Donald Trump we’re talking about, one might search no further than Occam’s Razor: he’s essentially a walking, pathological id who struggles to makes coherent plans of any kind.

So it could easily be that there was never any scheme, strategy, or purpose here. Trump’s launched ridiculous lawsuits and been rewarded for them before (see: ABC, CBS), like a child spoiled by jumpy parents who give in to every tantrum. And acting on craven impulse is a strong baseline explanation for a lot of Trump’s behavior. That could be the end of the story.

In fact, it wouldn’t even be all that unusual outside of Trump-world. A surprising number of major government decisions are made without a strategic plan or clear endgame in mind. Watching House of Cards gives the impression that government is populated by strategic masterminds. In my experience on Capitol Hill, that’s sometimes true, but often not. Elected leaders frequently hatch hazy ideas and leave it to staff to sort out the details and make something happen. That can lead to inane results.

So, can we imagine that what went down here was a quintessentially Trump decision to launch a patently deranged lawsuit followed by the DOJ scrambling to find a face-saving way out that didn’t involve telling the emperor he had no clothes? Absolutely.

But there’s a bit more going on that might provide an even better explanation...

Theory Two: It’s All About the Money

Another good starting point for understanding any Trump action is to assume it’s all about grabbing for money. And there’s a humdinger of a financial incentive hidden inside this settlement: the deal ends—forever—an I.R.S. audit of Trump’s tax returns that’s been hanging over his head for years and that could easily have cost him over $100 million.

That audit was quietly put on hold during the first Trump administration—and clearly was not going to move while he was president again—but could have been revived in the future.

Why not simply tell the I.R.S. to quash it? Because that’s blatantly against the law: 26 U.S. Code § 7217 prohibits executive branch influence over taxpayer audits and other investigations in language so plain not even Samuel Alito could fudge it.

So, under this theory, the story would look something like this. The $10 billion lawsuit was always a cover meant to obscure the ultimate target of ending the audit. The new settlement fund agreement is like draping Harry Potter’s invisibility cloak over what amounts to a secret $100 million payout to Trump. The Trump team may have even factored in the political backlash to the settlement as a lightning rod: a useful, trollish diversion from the real purpose. This would also fit Trump’s pattern of behavior of distracting from political scandals by creating even bigger political scandals.

In this version, the settlement fund and payouts to MAGA felons is a sideshow. But there’s also a strong possibility—one that I think is perhaps the most likely—that it’s the main show…

Theory Three: The RICO Contingency

To understand this explanation, let’s start out with a huge hat tip to Substacker Christopher Armitage for his May 4th article titled “This is way bigger than RICO. Is There a Legal Strategy That Could Put the Entire Trump-GOP Criminal Enterprise in Jail Without Waiting for an Election?”

Here’s the TL; DR:

The combination of the Supreme Court’s presidential criminal immunity ruling, the president’s pardon power, and Trump’s complete corruption of the Department of Justice has wrapped Trump and all of his minions in a protective bubble of freedom from federal prosecution.
But state laws still apply. And if any of them breaks a state law, even in the course of performing federal duties, they can (and should) be prosecuted.
So there is a potential to go after Trump’s criminality by using the exact same RICO model that prosecutors used in the 1980s to break the New York mafia: indict the lowest-level operatives, get them to testify against their bosses, flip those bosses and turn them against the next level up, and so on. Before long, you’re at the top.

The idea is that Trump is like the Death Star: he wields immense power at large scales, but he’s vulnerable to a small-scale attack that can set off a chain reaction. And he’s intimately familiar with this kind of vulnerability. His world is New York in the 1970s and 1980s. His lawyer, and idol, was Roy Cohn—a prominent fixer and consigliere for the same New York mob families who were eventually destroyed by RICO prosecutions.

We also know that his team actively wields the power of money to try to keep the lowest levels in line. Former Trump White House aide Cassidy Hutchinson testified to how the Trump team leveraged financial pressure and the promise of payouts to try to keep her from turning. As Greg Olear has pointed out, in just the past month, Trump’s DOJ has been quietly slipping substantial “settlement” baksheesh to risible MAGA figures like Mike Flynn and Carter Page, because mafiosos need to show their current foot soldiers that you will take care of them by taking care of previous foot soldiers.

All of this leads to the tantalizing possibility that the purpose of the settlement fund is exactly what it looks like: to take care of the last crop of pawns to prevent them turning, and to show the current crop that you are doing so.

And I say tantalizing because it is also a remarkable admission of weakness. If Trump and his team are so willing to court the kind of outrage that we are now seeing, and if they are truly motivated by the ability to give out these kinds of payoffs, it shows that they recognize a deep vulnerability. And it lights a path for state-level prosecutors to follow.

The settlement fund may look like pure brazen corruption — and it is. But if Theory Three is right, it’s also a map. State prosecutors, opposition researchers, and journalists should be reading this not as provocation to outrage, but as the entry point to a maze that says “start here” and that ends with holding a band of criminals accountable.

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