Quick: Which of President Donald Trump’s second-term executive orders currently threatens to do the most damage to our collective political order?

Birthright citizenship jumps to mind. But Trump’s effort to shred our 150-year old conception of citizenship, freedom, and equality has been blocked by the federal courts from the start, and has never gone into effect. Based on oral argument in the Supreme Court in April, Trump’s attempted redefinition is all but certain to fail.

Global emergency tariffs would’ve been a contender, as they temporarily threw international markets into disarray. But the Supreme Court invalidated the President’s unilateral “Liberation Day” scheme in February.

Trump’s executive actions attacking universities, media outlets, and law firms are anathema to core First Amendment notions of free speech and association. But the President’s bullying tactics have been uniformly rejected by the federal courts, and have blessedly little chance of ever becoming law. (Though we can’t discount the chilling effect, as many of the targeted institutions meekly chose to “settle” with the administration rather than fight.) 

Allow me to nominate a little-noticed contender: Trump’s March 2026 executive order absurdly titled, “Ensuring Citizenship Verification and Integrity in Federal Elections.” 

Again, this one hasn’t attracted much attention. Part of that is a function of sheer volume. In his first year-plus back in office, Trump has issued a torrent of executive orders – over 250 so far, already more than Joe Biden or his own first term and just under Barack Obama’s output over eight years. Trump’s executive order on elections also hasn’t drawn intense public scrutiny because it doesn’t attack the Constitution quite as aggressively as birthright citizenship, or seek to remake the global economy like tariffs. And the order’s language is dense and confusing; it’s hard to tell, on first reading, what it actually does. 

But when we cut through the bureaucratic gibberish, we can see the mayhem it would wreak. 

The order, first, requires the Department of Homeland Security to compile a “State Citizenship List” of eligible voters, to be “derived from Federal citizenship and naturalization records, SSA records, SAVE data, and other relevant Federal databases” and then delivered to state election officials. The order is cagey about what exactly those state officials can do with these federal master lists, but it contemplates that states can cross-check them against local records and use them to purge eligible voter rolls (wink, wink): “Well, I see that you’re registered to vote in this state, but you don’t appear on the new, federally-created master State Citizenship List, so sayonara.”  

Of course, it’s hard to see how DHS can generate from scratch state-by-state lists encompassing nearly two hundred million of voters by Election Day – nevermind by the order’s deadline of 60 days before the election. No such lists exist now, as the order recognizes; indeed, the order doesn’t even know which federal databases might exist for these purposes: “and other relevant Federal databases.” (Did you have any in mind?) 

Even if DHS does manage to slop together these lists culled from assorted, partially-overlapping but distinct federal databases, there’s no way to ensure their reliability. Are any of the listed voters actually ineligible? Do the lists omit voters who are eligible? In a court hearing last week, a Trump administration lawyer conceded that the State Citizenship Lists are bound to be flawed: “No list is ever going to be perfect,” a DOJ lawyer shrugged. 

It gets worse. Trump’s executive order instructs the U.S. Postal Service to design a new, high-tech, elections-only super-envelope. Our cutting-edge mailers must be “automation-compatible” with “designated markings provided by USPS,” including a “unique Intelligent Mail barcode” that “facilitates tracking,” and – just for good measure – anything else “consistent with the other requirements of this section.” Turns out, the Postal Service is just as baffled as anyone else, and informed a federal court last week that it was still deliberating and had not “reached any final decisions about the substance of a proposed rule.” Translation: This executive order is completely unworkable, so we’re spinning our wheels while hoping a court strikes it down so we don’t have to deal with this impossible mess. 

There’s a dark purpose lurking here, beneath the confusion of it all. Trump’s executive order instructs the Postal Service that it can distribute these new envelopes only to people listed on the aforementioned State Citizenship Lists. And the order tells the Postal Service that it can deliver mail-in ballots only in the designated envelopes. As a practical matter, then, any person who does not appear on the dubious, federally-created State Citizenship Lists (1) can be kicked off state voter rolls and (2) will not receive a mail-in ballot, and can’t vote by mail. 

Trump’s executive order now faces a legal challenge in federal court, where two obvious problems loom. First, there’s just no way DHS or the Postal Service can comply with the order’s outrageous demands. Both have made that clear already in their court filings; DHS can’t realistically put together State Citizenship Lists with any degree of reliability, nor can the Postal Service design, manufacture, and distribute the new election-specific envelopes before September. 

Second, Trump’s executive order is facially unconstitutional. Article I’s Elections Clause is about as clear as things get in our seminal parchment: “The Times, Places and Manner of holding Elections for Senators and Representatives, shall be prescribed in each State by the Legislature thereof; but the Congress may at any time by Law make or alter such Regulations.” So elections are up to the states, unless and to the extent that Congress passes laws regulating those elections. Easy. The Constitution purposefully gives the Executive Branch no power to administer elections.

Trump tries an end-run with his executive order. It purports to regulate not elections per se, but rather DHS and the Postal Service, which fall within the Executive Branch. But the instructions Trump gives to these agencies would upend the voting process, in conflict with the power granted by the Constitution to the states and Congress. Imagine if, for example, a president instructed the Army Corps of Engineers to build twelve-foot alligator moats around all polling places. Technically, he’d merely be giving instructions to one of his own Executive Branch agencies – but he’d certainly compromise state and Congressional control over elections in the process.

Despite the apparent unconstitutionality of the order, federal district court Judge Carl Nichols – a 2019 Trump appointee who has rejected prior efforts by Trump to expand executive power – did not strike it down swiftly. At a hearing last week, the Judge wondered aloud if it might still be too early to act: “Why is there irreparable harm now?” he asked, “What if they don’t remove a single voter?” (Good luck with that.)  But he promised to rule quickly and warned the government not to further implement the order until he issues a decision.

I believe the courts ultimately will strike down Trump’s executive order on elections. That outcome is not guaranteed though, and there’s much uncertainty about when and how it will meet its ultimate fate. Thus far, this order has escaped much public notice. But if it is implemented, even in some modified form, it will plunge the upcoming midterm elections into chaos.