Scott Bessent, who was confirmed as Treasury Secretary on January 27, 2025, has been serving as acting IRS Commissioner since August when Trump unceremoniously dumped Billy Long from the role just two months after his confirmation. That makes Bessent the seventh person to lead the IRS since Trump won the 2024 election—a turnover rate that would make a fast-food franchise blush.

So when Trump filed his lawsuit Thursday night accusing the IRS of allowing unlawful disclosure of his tax records, he wasn't just suing a faceless bureaucracy. He was effectively suing an institution currently run by his own hand-picked finance chief. It's the administrative equivalent of punching yourself in the face and then demanding damages for assault. And yet—here's where it gets interesting—Trump is probably right.

The facts are straightforward enough to be damning. Charles Littlejohn, a former IRS contractor, pleaded guilty in October 2023 to stealing Trump's tax records and leaking them to The New York Times. Littlejohn also provided ProPublica with tax data from thousands of wealthy individuals. For this unprecedented breach, he received a five-year prison sentence—hardly a deterrent for what prosecutors called one of the most consequential leaks of taxpayer information in modern American history.

Federal law is unambiguous on this point: the unauthorized disclosure of tax information carries strict liability. The law doesn't care about noble intentions or journalistic value. It exists to ensure that when Americans hand over their most sensitive financial information to the government, that government won't turn around and hand it to the press.

Trump's legal team argues, correctly, that Littlejohn's conviction doesn't absolve the IRS of responsibility for systemic failures that enabled the breach in the first place. The agency's lapses in oversight and data security created the conditions for an ideologically motivated contractor to waltz out with the crown jewels in Trump's legal crosshairs. And Trump has filed a $10 billion lawsuit against the BBC in federal court in Florida over allegedly deceptive editing of his January 6 speech.

Trump himself once told The Washington Post about a lawsuit against journalist Timothy O'Brien: "I spent a couple of bucks on legal fees, and they spent a whole lot more. I did it to make his life miserable, which I'm happy about". That's not justice. That's strategy.

Let's tally the damage. Trump has extracted settlements from Meta and X for de-platforming decisions. He's won sizable settlements in cases legal scholars dismissed as largely lacking merit. He's suing CNN, The Wall Street Journal, The New York Times, and recently targeted pollster Ann Selzer for getting Iowa predictions wrong—despite winning the state by 13 points.

The pattern is unmistakable: file audacious lawsuits demanding astronomical sums, force defendants into expensive legal battles, and extract settlements from corporations with regulatory interests before the Trump administration. Some commentators have suggested these settlements constitute "a novel pathway to engage in political bribery"—though proving that would require penetrating corporate board deliberations that will remain forever sealed.

What's clear is the chilling effect. If even media giants such as ABC and CBS are settling rather than fighting, what local news editor is going to assign a story that might trigger a presidential lawsuit?

Trump at one point suggested the Justice Department should be handling these cases. "I feel I have to do this," he told reporters. "I shouldn't really be the one to do it. It should have been the Justice Department or somebody else. But I have to do it."

Here's what makes the IRS lawsuit particularly perverse: Trump is simultaneously arguing that the agency failed to protect his information while presiding over an administration that has weaponized taxpayer data for immigration enforcement.

Under Trump's IRS leadership, the agency has churned through seven different leaders since the 2024 election and lost 25% of its workforce. One acting commissioner, Melanie Krause, resigned in April after Trump allies pushed through a deal to share sensitive taxpayer data with immigration agencies.

So the IRS can't be trusted to protect Trump's tax information, but it can be trusted to share your tax information with ICE? The cognitive dissonance is staggering. This isn't governance. It's selective accountability dressed in legal briefs.

Bessent, who took over the IRS after Trump removed Billy Long from the post, now faces an impossible task. As Treasury Secretary, he must defend the institution against Trump's lawsuit. As a Trump appointee, he serves at the pleasure of the president suing his own agency. As acting IRS Commissioner—the sixth acting head during the Trump administration—he must somehow restore confidence in an institution his boss is publicly declaring incompetent. The man is simultaneously plaintiff, defendant, and referee.

When Bessent visited IRS headquarters in August as the new acting commissioner, he highlighted the agency's record-setting tax collection and reminded employees about modernizing IT systems. One imagines he did not mention that the president was preparing to sue them for $10 billion.

Trump's allies argue this demonstrates the president's independence from bureaucratic capture—that he's willing to hold even his own agencies accountable when they fail. It's a convenient narrative that ignores the fundamental question: How can an agency function when its ultimate boss is its most aggressive legal adversary?

Forget the specific merits of the IRS case. Focus instead on what Trump has normalized: a president who treats litigation as routine political strategy, who uses the courts not as a last resort but as a first response, and who sees financial settlements from corporations with government business as victory rather than corruption.

Trump has been involved in more than 4,000 lawsuits over the course of his life. Many involved suing for defamation over perceived threats to his reputation. He's brought this litigious worldview into the Oval Office and somehow convinced half the country it's normal. It's not normal. It's corrosive.

Every lawsuit Trump files against media organizations, polling firms, and now his own government sends an unmistakable message: Criticize me, get my facts wrong, or fail to protect my interests, and I will make you pay. Literally.

The doctrine is simple: Comply or Pay. Cooperate with the Trump narrative or face eight-figure legal expenses defending against frivolous claims. Settle and apologize or risk regulatory retaliation through agencies Trump controls.

It's not quite authoritarianism—the courts still function, the settlements are technically voluntary, and Trump faces real legal constraints. But it's not exactly freedom of the press either when the president systematically uses lawsuits to extract tribute from media corporations with business before his administration.

Return now to the IRS lawsuit's core problem: If Trump can't trust the agency to protect his tax returns, why should anyone else trust it with theirs?

The president has just announced to 150 million taxpayers that the IRS is institutionally incompetent at its most fundamental obligation—safeguarding confidential information. He's declared that even with all the resources of the federal government, even with his own Treasury Secretary running the agency, even with his power to fire anyone who crosses him, the IRS remains so systematically broken that only a $10 billion lawsuit can provide accountability.

He may be right about the breach. He's certainly right about Littlejohn's criminal conduct. He's probably right that the IRS deserves to be held liable for systemic failures. But he's catastrophically wrong about the consequences of this public warfare against his own government.

Every American who files taxes in April will now do so with Trump's implicit warning ringing in their ears: This agency cannot be trusted with your most sensitive financial information. The president himself doesn't trust it. Why should you?

The ultimate irony? Treasury officials like to note that federal tax receipts increased 14.7% in May from 2024, bringing in $2.04 trillion through tax season—a $100 billion increase from the previous year. Bessent, during his visit to IRS headquarters, highlighted the agency's record-setting tax collection.

So the IRS is simultaneously incompetent enough to warrant a $10 billion lawsuit and competent enough to collect record revenues for the president suing it.

Welcome to Trumpian governance: You can't trust the tax collector, but you'd better pay up anyway. The agency is broken, but the money keeps flowing. The leadership is a revolving door, but the collections hit record highs. The president sues his own government while his Treasury Secretary defends it while running the agency being sued.

It's government as paradox, accountability as performance art, and institutional confidence as collateral damage. Trump will probably win his lawsuit eventually. The law is on his side. Littlejohn committed a crime, and the IRS failed to prevent it.

But the real damage won't show up in any settlement. It's already done: A president has declared war on his own tax collection agency, undermined public confidence in taxpayer privacy, and demonstrated that no institution—not the press, not polling firms, not even his own government—is safe from his "Comply or Pay" doctrine.

The precedent is set. The message is clear. The system is weaponized. And Scott Bessent has to defend both sides of this litigation while somehow convincing Americans their tax returns are safe. Good luck with that. (IPA Service)