Washington in August is a sleepy town, but not for the federal judges who spent their summer getting overruled. At the center of the storm is President Trump’s Executive Order No. 14,399, signed March 31, 2026, which aims to tighten mail-in voting rules. The order, as explained by legal analyst Bill Shipley in American Thinker, has become a lightning rod for five lawsuits filed in April by Democratic allies. Two judges — one in D.C., one in Massachusetts — have taken sharply different paths, and the Supreme Court may be about to settle the score.
The Order’s Core Mechanics
The executive order directs the Department of Homeland Security to work with federal agencies to create state-by-state lists of U.S. citizens eligible to vote in the next general election, then send those lists to the states. It also orders the U.S. Postal Service to establish a system where states can notify USPS of their intention to use the mail for voting, and provide a ‘Participation List’ of enrolled mail-in voters. USPS would not deliver election mail to or from anyone not on that list, and would use unique identifiers like barcodes on ballot-return envelopes to match mail to voters. Eligible voters not on the list can still vote in person.
Shipley, in his analysis, argues this order may be ‘a more significant measure than the stalled SAVE Act.’ The USPS, which processes over 35 million pieces of mail daily using sophisticated optic scanning devices, already has regulations for mailers and a criminal investigation arm — Postal Inspectors — to prevent election-related fraud. According to Shipley, it’s hard to argue USPS is overstepping by trying to secure the mail-in process.
The D.C. Disappointment for Plaintiffs
Three of the five lawsuits were filed in D.C., and the plaintiffs likely expected a friendlier forum. They tried to have the cases assigned to ‘a Senior Judge with a long track record of anti-Trump decisions,’ but instead, Judge Carl Nichols got the cases. Nichols denied their motions for injunctive relief, ruling that the plaintiffs ‘did not allege any injuries that could be remedied, either actual or imminent stemming from the issuance of the E.O.’ The order itself did nothing — it merely set up a rulemaking process, and challenges would have to wait until that process concluded. The D.C. Circuit Court of Appeals unanimously affirmed his decision.
Massachusetts: A More Sympathetic Ear
Across the river in Massachusetts, Judge Indira Talwani, described as ‘notoriously anti-Trump,’ took a different tack. She blocked implementation of several key provisions of the executive order in the 23 states that joined the lawsuit — but couldn’t reach the other 27 states not party to the suit. The First Circuit Court of Appeals denied the DOJ’s motion to stay her injunction in a 2-1 vote, and the DOJ has since filed an application for a stay with the Supreme Court.
In a second case brought by the League of Women Voters, Talwani went further, enjoining the creation of the Participation Lists and the design of a standard election mail envelope in all 50 states.
Shipley argues that Talwani’s reasoning — which focused on ‘election mechanics’ left to the states — misses the point. The transmittal of ballots via the mail, he contends, falls under federal authority. ‘USPS is a federal agency over which the states have no say in how it operates — and that should include delivery of election-related mail for the states,’ Shipley writes.
Waiting on the High Court
The Supreme Court now has a pending application for a stay on Talwani’s original order, and observers are waiting to see what happens. Shipley wonders whether the Court is holding off to combine both Talwani cases, or whether a dissenting justice is writing a rejection. His conclusion: ‘Either way, we should have an answer from the Court soon.’ He puts his money on Talwani being overturned.
A TPS Judge Backs Down
Another judge, Allison Burroughs, also drew attention this summer. In a case involving temporary protected status (TPS) for Somali nationals, Burroughs granted an administrative stay of the order terminating that status. But the Immigration and Nationality Act clearly states there is no judicial review of the Secretary of Homeland Security’s TPS determinations, and the Supreme Court in Mullin v. Doe made clear that district courts lack jurisdiction over non-constitutional TPS claims.
Adding to the controversy, just days before Burroughs’s ruling, the First Circuit had reversed similar stays issued by two other judges in the circuit — Murphy and Saris — for immigrants from Ethiopia and South Sudan. In response, Congressman Andy Ogles filed a bill of impeachment against Burroughs. Almost immediately, she reversed herself, acknowledging that the challengers had no right to an extension, that Mullin controlled, and that her original ruling was wrong.
The Bigger Picture
These cases highlight a pattern, according to Shipley: lower court judges trying to ‘hamstring the Administration’s agendas despite what higher courts have ruled.’ The mail-in voting order, though, is far from settled. With the Supreme Court set to weigh in, the summer’s judicial battles may soon give way to a definitive ruling.
As Shipley notes, the stakes are high for both sides. The executive order could reshape how millions of Americans cast ballots, and the legal fights over it are just beginning.
Source: www.americanthinker.com — https://www.americanthinker.com/articles/2026/08/leftist-judges-fighting-a-losing-battle/