Boasberg's Coincidental Contempt Timeline

As we await the judge's contempt finding, a careful review of court filings and transcripts demonstrate how Jeb Boasberg set up the Trump administration from the early hours of March 15.

Any day now, D.C. District Court Chief Judge James Boasberg will file an opinion detailing what last week he called “probable cause” that the Trump administration defied one of his court orders halting the deportation of illegal Venezuelans tied to Tren de Aragua.

The Supreme Court on Monday vacated two written restraining orders Boasberg issued on March 15; what remains is Boasberg’s “oral ruling”—as he describes it—to return planes already in the air that day. That verbal command represents the basis of Boasberg’s contempt allegation.

But any contempt inquiry into the Trump administration will be the result of what appears to be a trap Boasberg carefully constructed from the moment he got the case. In fact, in order to believe Boasberg did not set and build a contempt case against the Trump administration, one must believe a set of coincidental events that got the ball rolling on March 15:

• Within hours of President Donald Trump’s nonpublic signing on March 14 of the Alien Enemies Act (AEA) proclamation, which authorized the immediate deportation of illegal Venezuelans who are members of TdA, the American Civil Liberties Union just happened to quickly prepare and file a lawsuit seeking to halt those deportations on behalf of five unnamed illegals set for removal to Central America.

• The lawsuit, filed shortly after 1:00 a.m. on March 15, landed in Boasberg’s inbox at 7:25 a.m. As chief judge, according to Boasberg, he had to authorize the filing of a lawsuit on behalf of anonymous plaintiffs. And despite the fact Boasberg was “away” for the weekend (his words), he just happened to be open for business in the early hours of a weekend getaway. “Only because I was available and could review first the pseudonymous motion, which I had to review as chief judge, and then the case was then transferred to me or assigned to me. And so it was good fortune (emphasis added) that…the only reason why they were able to get relief that morning before those people were put on the plane,” the judge said during an April 3 hearing.

• Despite the fact the court was closed on Saturday—which Boasberg admitted in the same proceeding—and the fact another D.C. judge was assigned to the emergency docket for the weekend, the lawsuit just happened to stay on his desk.

• At 9:40 a.m., without any input or briefing by the Trump Department of Justice, Boasberg just happened to have seen enough evidence to issue his first temporary restraining order banning the removal of the five illegal Venezuelans represented by the ACLU.

But that wasn’t enough for the ACLU—or, apparently, for Boasberg. The judge scheduled a March 17 hearing to consider the ACLU’s request to convert the initial case into a class action lawsuit covering anyone subject to the AEA.

After behind-the-scenes back and forth with the ACLU—and amid inside knowledge some flights would depart later in the day—Boasberg then added an emergency hearing for 4:00 p.m. on March 15 on the class action question.

There was, however, a problem.

The proclamation had not yet been issued by the White House so, according to procedure, it was not yet active. Boasberg pushed the March 15 hearing back to 5:00 p.m., presumably with fingers crossed the Alien Enemies Act was official by then.

But there is more sketchiness to the postponement. Boasberg knew planes carrying the AEA subjects planned to take off that evening, indeed, during the 5:00 p.m. hearing.

And that’s when Boasberg’s contempt trap was set.

Who’s Calling Who “Sketchy?”

The White House finally posted the proclamation at 3:53 p.m.; Boasberg and the ACLU were in business.

Department of Justice attorney Drew Ensign appeared on behalf of the Trump administration during the virtual hearing. Boasberg opened the hearing by apologizing for his attire—— “I went away for the weekend and brought with me neither a robe nor tie nor appropriate shirt, so thank you all for being appropriately attired and hope you will forgive my casual ones”—and then began grilling Ensign as to the status of the deportation flights.

The plaintiffs, Boasberg said, had “alert[ed] my chambers…that they expected planes to be departing within the last couple of hours.” The ACLU attorney confirmed as much by telling Boasberg, “our understanding from people on the ground, from different sources, is that planes are going right now taking Venezuelans to El Salvador. [Two] flights that we believe were scheduled for this afternoon that may have already taken off or during this hearing.”

That prompted Boasberg to ask Ensign for details about the flights. “Can you tell us, Mr. Ensign, are imminent deportations and removals under this proclamation planned? When I say imminent, I mean in the next 24 or 48 hours.”

And when Ensign could not answer the question—it was a Saturday evening after all—Boasberg, who later said what transpired on his watch that day was not “anything close to common”—took a convenient break in the hearing to allow Ensign to “do some digging” about the status of the flights.

It was 5:22 p.m.. And that’s when another set of coincidental events took place.

• During the break, two planes headed for Central America carrying AEA subjects just happened to take off from Texas: one at 5:26 p.m. and one at 5:45 p.m.

• When the hearing resumed at 6:00 p.m. and Ensign had no answer for Boasberg about the flights, the judge just happened to boldly conclude he had enough evidence—despite admitting he conducted little research into the matter and the fact the DOJ “haven't had an opportunity to brief it”—to convert the case into a class action lawsuit covering “all noncitizens in U.S. custody who are subject to the March 15, 2025, Presidential Proclamation.”

• After once again confessing “everybody here is operating on the fly” and openly acknowledging the court’s lack of authority in reviewing the president’s AEA, Boasberg just happened to determine that he nonetheless could order the return of deportation planes en route to Central America. “Mr. Ensign, you shall inform your clients of this immediately, and that any plane containing these folks that is going to take off or is in the air needs to be returned to the United States, but those people need to be returned to the United States,” Boasberg said at 6:45 p.m. “However that's accomplished, whether turning around a plane or not embarking anyone on the plane or those people covered by this on the plane, I leave to you. But this is something that you need to make sure is complied with immediately.”

• But in his written minute order posted around 7:26 p.m. prohibiting the Trump administration “from removing members of such class…for 14 days,” Boasberg just happened to omit the part about returning planes carrying the instantly-designated class of illegals.

The Trump administration insists Boasberg’s verbal orders are not controlling; case law and common practice appear to support the administration’s argument. Top Trump officials including Attorney General Pam Bondi have invoked state secrets privilege to keep detailed information about the March 15 flights away from Boasberg—something the judge last week called “sketch[y].”

But Boasberg, of course, is the sketchy one. Since setting the contempt trap on March 15, he has publicly advanced the notion the administration did not obey his orders, going so far as to recently demand the names of Trump officials who may have listened to the March 15 hearing and suggest he would seek depositions to determine who knew what when.

Talk about contempt.