Guest Post: A defense of the Justice Department $1.776 billion giveaway to Trump

I wrote that the $1.776 billion slush fund deal stank to high heaven.

It should be the item that finally -- finally! -- convinces Republicans that Trump is a dangerous and corrupt con man.

Then I invited a Republican reader to tell me why I am wrong. College classmate Matt Naitove agreed to do so.

 
Naitove earned an MS degree at the Columbia Graduate School of Journalism and then accepted a first job, which became a lifelong career, at Plastics Technology magazine. He retired from that publication after 51 years. Naitove has voted for Donald Trump and he has defended him in this blog. He writes that Democrats have dirty hands when it comes to the prosecution of Trump and his associates, and in that context, Trump's Justice Department deal is a response that should not surprise to Democrats.

Naitove

Guest Post by Matt Naitove

Trump v. IRS – the ‘Final Straw’?

How can it be defended? Peter Sage asked the question after stating in his blog that the settlement between Donald Trump and his own IRS of a lawsuit that he (Trump) filed at the start of his second term was “the final straw” and “the utter corruption of the Justice Department.” Peter then generously invited “one of my Republican readers” (myself) to defend the presumably indefensible, if I could. Now that’s the Harvard spirit of open debate! (Or I wish it were.)

So I said I’d give it a whirl. Which is not so easy, because I wish it had never happened. It’s a big ugly mess that looks questionable on its face and takes much explanation to even try to justify. And of course it’s a big gift to Trump haters, as if they needed anything more to chew on.

But does that make it a hair-on-fire emergency to send Paul Revere off at a gallop to save our liberty? I don’t think so. Let’s start with a bit of background on the genuine scandals that precipitated the latest events. I refer to actions by the Biden Administration and their cronies that introduced the word “lawfare” into common parlance. President Trump himself was subjected to a barrage of fanciful and vaporous suits and indictments, almost none of which will be left standing ultimately, I predict. His income tax filings were released to the public, in clear violation of the law. And even FBI insiders consider the agency’s raid on Mar-a-Lago for “missing documents” to have been unprecedented and unwarranted.

Trump’s lawsuit against his own government also sought relief for the preposterous “Russia-collusion hoax” (to quote the settlement agreement), which was abetted by both the Obama and Biden administrations, and which swept many more of his associates into its maelstrom.

More than half a dozen of Trump’s former lawyers and associates have been subjected to disbarment, threat of disbarment, or even imprisonment for flimsy charges (in my opinion) related to objecting to elements of the 2020 presidential election. (May I remind readers that many Democrat legislators –Jamie Raskin, Nancy Pelosi, Maxine Waters, among others – have stood up in the House of Representatives while the Vice President is certifying slates of electors, to protest those slates for certain states after the 2016 and 2024 elections. something that is perfectly within the rules.) One of those former Trump lawyers, I have heard repeatedly on Fox News, was forced to spend $2 million of his own money on legal fees, which is precisely the purpose of lawfare: to sap an opponent’s time, energy and finances, regardless of the ultimate legal outcome.

Then there have been the nonviolent religious objectors to abortion that have been caught up in the maw of the legal system, as well as “the Biden Administration’s wrongful labeling of certain parents as domestic terrorists” (again quoting the settlement agreement). And, among the hundreds of prosecutions ruthlessly pursued by Biden’s DOJ for Jan. 6 infractions, some were richly deserved, but many were not, despite long pretrial incarceration under miserable conditions in the D.C. jails.

Are there good arguments for some form of reparations to those unjustly injured by partisan lawfare? Maybe so. But is this the way to do it?

-- The IRS employee, Charles Littlejohn, who leaked Trump’s and others’ tax returns was convicted and imprisoned. So why did Trump then file suit against what was now “his” IRS? Can’t say, other than it clearly gave him more leverage. But it certainly created a constitutionally awkward situation. (Trump was not alone in such a move, however. Hedge-fund manager Ken Griffin sued the IRS and the Dept. of Treasury for leaking his tax returns, but he received an apology after Littlejohn was convicted and dropped his suit.)

-- The agreement agrees “to ACQUIT and FOREVER DISCHARGE” and be “FOREVER BARRED and PRECLUDED” from pursuing tax claims against Trump, his sons and the Trump Organization LLC that “have been or could have been asserted” by the U.S. as of May 18, 2026. I don’t know any of the merits of those cases, since they have not been publicized. Littlejohn’s goal apparently was to show avoidance of paying taxes, not in itself a crime, since the whole U.S. tax code is an accretion of loopholes, carve-outs, exceptions and pretexts for tax avoidance. Would individuals and an organization as much in the public eye as Trump have pushed those elastic guardrails beyond legal limits? Who knows? But did the official settlement have to include all-caps to make it sound like Trump’s posts on Truth Social? And the phrase “have been or could have been asserted” is bound to raise eyebrows.

-- Then there’s the “Anti-Weaponization Fund.” Oh boy. The settlement says the size of the fund is based only on “the projected valuation of future claimants’ claims.” And that’s exactly $1.776 billion? Come on. That’s an awful lot of money for such a purpose. Who will get it? Not the Trumps, the settlement seems to state. It looks very messy to decide who will qualify and for how much. Could former FBI chief James Comey claim to be victim of lawfare from Trump’s Administration? Whatever happens will no doubt engender much blowback. The article cited below from the New York Times, not a Trump-friendly publication, gives an admirably clear-headed appraisal of the many unknowns in this agreement.

Lawfare is deplorable, no doubt. Is it now an indelible part of our political cage match? Does this agreement discourage it, or the opposite? I don’t see the merit of establishing another government payout mechanism with a big pot of cash and vaguely defined purposes and eligibility criteria. No, I’m not a fan.

Sources:

Trump v. IRS
https://www.justice.gov/opa/media/1441201/dl

“Justice Department Announces Anti-Weaponization Fund” https://www.justice.gov/opa/pr/justice-department-announces-anti-weaponization-fund

“How the Administration’s $1.8 Billion Fund May Violate Past Practice and Policy”.
https://www.nytimes.com/2026/05/20/us/politics/trump-fund-explainer.html?unlocked_article_code=1.llA.VJ2Q.UuIk3VY9XPXO&smid=url-share

Trump v. Internal Revenue Service – Wikipedia
https://en.wikipedia.org/wiki/Trump_v._Internal_Revenue_Service

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