DEMOCRACY WATCHUSPS Plays a 'Puzzle Game' With the Right to Vote

By Molly Roberts

Published 9 September 2026

Months away from elections, a federal judge worries President Trump’s mail-in voting executive order could cause disenfranchisement.

Justice Kentanji Brown Jackson, dissenting from the Supreme Court’s decision to stay a preliminary injunction against implementation of President Trump’s executive order on mail-in voting, wrote that allowing the plan to proceed could “foment chaos” ahead of the upcoming midterm elections. You’ll never guess what happened next.

Following a weeklong litigatory blitz involving myriad motions by multiple plaintiffs in two jurisdictions, the United States Postal Service’s final rule—issued at 9 p.m. on the Friday before the Monday on which the Supreme Court ruled the challenge wasn’t ripe for review because there was no final rule—got its day in court on Sept. 3.

“I don’t think anyone can be accused of slow-walking anything,” Judge Indira Talwani says upon taking her seat on the bench at the John Joseph Moakley Courthouse overlooking a drizzly Boston Harbor. She’s hearing combined arguments in League of Women Voters of Massachusetts v. Trump and State of California v. Trump on revised motions for a preliminary injunction that would supersede the temporary restraining order (TRO) she has already put in place. The Justice Department has already appealed the TRO to the First Circuit (this despite TROs being generally understood to be unappealable), and its opening move in the hearing evinces a similar need for speed: Rule today, its lead counsel says, or we’re going to take the appeal all the way to the Supreme Court.

Judge Talwani provides a spoiler for what to expect from the hearing—or rather, what not to expect. She never rules from the bench, she says, and she doesn’t plan to today. The administration, as promised, appealed the TRO to the Supreme Court before close of business, in a highly irregular and possibly impermissible step.

The desire to move fast in order not to break things permeates the rest of the proceedings. This is no surprise. The election is under 70 days away, and some states are slated to send out mail-in ballots this very week. Both sides have cast a loss under these circumstances as causing them irreparable harm: the plaintiffs because they may be forced to comply with unlawful rules that will disenfranchise voters, and the defense because they may be unable to implement lawful rules that they claim will enhance election integrity.

There’s a certain irony to this. The government had previously insisted that it wasn’t too early for the merits to be considered. Now, suddenly, it seems to have become too late.