Losing My Perspicacity, October 27, 2025

Good morning and Happy Monday! Thanks for reading along today.

We had quite a few legal developments late on Friday. I spent more than two hours on Friday morning, which I had promised myself I would take off, covering the oral arguments in Oregon v. Trump. The whole thing wound up feeling more like a law school exam question than an actual courtroom case, which is to say that I got a screaming headache while live-posting the updates on Bluesky, and it’s been here ever since, with an assist from the Chicago Bears’ offensive line.

More on that in a minute.

Before we get into the legal wrangling, I want to share a bit of what it’s like to live in a city that’s under siege by ICE and Border Patrol. I know we talk a lot about what’s going on in Chicago, but, as I’ve said many times, Chicagoland encompasses hundreds of suburbs on the North, South, and West sides. We are all feeling the pinch, especially if you live in a heavily Latino community like I do.

Aurora, IL, is the second-biggest city in Illinois, after Chicago. While Aurora was once a booming outpost on the Fox River, it was eventually absorbed as the Chicago suburbs crept West. Aurora has a rich history of its own — we were the first city in America to have lights across the entire town. You’re probably more familiar with our tony neighbor, Naperville, but there are many here in Aurora, like my family, who moved here from Naperville because we wanted to live in a more diverse community (though Naperville is more diverse than it once was). And Aurora is highly diverse. In 2020, more than 40 percent of our community was Latino, and we also have a large number of Black families and families from Southeast Asia who make up our friends and neighbors. Sadly, that diversity has made us a target for ICE.

On Saturday morning, I started hearing a helicopter hovering over my subdivision. I tried to get a good look at it, but when I couldn’t tell if it was headed to a nearby hospital, I called it in to our local Rapid Response team so they could get the word out that ICE might be in the area. For context, ICE and CPB have been massing in the big box store parking lots along Rt. 59 (the main corridor for Naperville and Aurora), which has entire blocks of stores dedicated to those of Indian and Asian descent.

I also posted about ICE being around in our neighborhood Ring group, which I hate, and was met with so many “Good, I’ll make sure my neighbors are outside to get picked up” comments that I was in a bad mood for the rest of the day.

Then, towards evening, Aurora Rapid Response posted this message on Facebook. It’s long, but I think it’s essential information.

Two US citizens were put in the hospital by ICE, and they were forced to leave their young child in the hands of the Aurora Police Department. At the hospital, ICE began assaulting protestors, and they took off with a US Citizen in their van. Thankfully, both people have now been released. Protestors also saw at least one ICE vehicle that was operating without a license plate, in violation of state law.

I’m grateful for our wonderful progressive mayor, John Laesch, who is currently getting harangued for having the gall to suggest that Aurora Police could actually be on the side of citizens in this war with jackbooted thugs. We also have a really great state representative in Barbara Hernandez, who was out at the hospital alongside Laesch, demanding answers.

My family is white — we all look incredibly white. I have red hair and green eyes; my oldest has blonde hair and blue eyes. We aren’t in danger of being harassed by ICE, but their presence in our community has affected our lives — I can’t imagine what it must feel like to be part of the Latino or other immigrant community. People are afraid to leave their homes, and businesses that rely on their ethnic communities to stay afloat are suffering.

All of this is to ask you all to get involved, however you can. Find a group supporting immigrant communities near you. Donate to local food pantries. Patronize businesses owned or operated by immigrants. Volunteer to respond to ICE incidents. Get a whistle and blow it like mad if you spot the feds harassing people. Catch whatever you can on video.

It’s going to take all of us to make it through this.

Today: What happened in Oregon v. Trump that is so confusing for everyone?; Greg Bovino gets ordered into federal court in Chicago; Trump cares more about this stupid ballroom than he has ever cared about anything; and The High Note.

Here we go.

Recapping Oregon v. Trump

On Friday morning in Portland, District Court Judge Karin Immergut held a hearing on whether she should dissolve the second temporary restraining order (TRO) she issued in Oregon/Portland/California’s lawsuit against Donald Trump over his attempt to deploy National Guard troops to Portland. Yes, the 9th Circuit Court of Appeals stayed Judge Immergut’s initial TRO, but then the case got way more complicated. I’ll do my best to explain.

When the plaintiffs (OR/CA/Portland) flew into court in early October, they sought a TRO to stop Trump from flooding Portland streets with the Oregon National Guard (NG). Immergut granted that TRO, prohibiting Trump from deploying the OR National Guard in Portland. A few days later, Trump and Pete Hegseth (and let’s be honest, Stephen Miller) attempted to use troops from California and Texas to get around Judge Immergut’s order. So back to court we went, and Immergut issued a second TRO, this time blocking Trump from deploying any National Guard troops, from Oregon or any state, in Portland.

The feds immediately appealed the first TRO, which was stayed by the Ninth Circuit, pending the outcome of a trial on the merits. But the DOJ never appealed the second TRO. So when the first TRO was stayed, meaning Trump could deploy the OR NG to Portland, the second TRO, which said no troops from OR or any other state, remained in effect.

The feds’ solution was to go to court and argue that, because Judge Immergut issued the second TRO based on the same analysis and facts as the first, the second had to be dissolved. But the plaintiffs argued that part of the reason Immergut issued the second TRO was that the feds were attempting to get around her first order, which shows the feds were acting in bad faith. After an hour and 45 minutes of back and forth and everyone arguing about how the case should proceed, Judge Immergut called a recess and promised she’d have a ruling by Monday morning. The case is set for trial on the merits on Wednesday, October 29.

BUT THEN! Chief Judge Emeritus Sidney Thomas, the same judge who, on his own, called for an en banc rehearing of the ruling of a three-judge panel from the 9th Circuit (which means he likely thinks the decision was bullshit), issued an order of his own, getting the parties and the three-judge panel who originally heard the case to extend the second TRO until Tuesday evening. By then, we should have a decision on whether the 9th Circuit will grant an en banc rehearing. The whole thing makes my brain hurt. It’s worth mentioning that the feds could have avoided this entire situation by appealing the first and second TROs, but they aren’t the brightest bulbs on the tree, clearly.

The bottom line is this: The 9th Circuit was once, by far, the most liberal appellate court in the country. Judge Sidney Thomas, a Clinton appointee, was the Chief Judge of the 9th Circuit from 2014 to 2021. He clearly doesn’t like the way this case has been handled by the two Trump-appointed judges who ruled in Trump's favor, and he still seems to have quite a bit of juice with his colleagues. While I would prefer we argue over something more interesting than how a temporary restraining order should be handled on appeal, this is as close to a soap opera as most legal cases get.

One final note: The plaintiffs filed a letter on Thursday, asking the 9th Circuit to overturn its ruling on the first TRO, because it was based on faulty information provided by the feds. Because the DOJ is increasingly run by attorneys who are in way over their heads.

You can read the letter below.

Greg Bovino was ordered into federal court for some answers

We had plenty of courtroom drama of our own here in Chicagoland on Friday, with the Chicago Headline Club (a consortium of various journalists and others) filing two Notices of Violation of TRO in Judge Sara Ellis’ courtroom. Last week, Judge Ellis forced the feds to bring in the ICE and CBP leads to answer questions about why her own TRO, which blocks ICE, among other things, from throwing tear gas at protestors in non-violent situations and forces ICE to wear both identification and body cams while operating in the Northern District of Illinois, was being violated by ICE and CBP agents.

Now that video and photos have emerged of CBP head Greg Bovino, himself, tossing tear gas canisters at bystanders in Chicago’s Little Village neighborhood, Judge Ellis has clearly had enough. This is the same judge who told the feds two weeks ago that, when she issues an order, “It is not a suggestion; it is not a jumping off point for debate. It. IS. AN. ORDER.”

Judge Ellis speaks very calmly and somewhat quietly, but even I took notice when listening to her from my couch. This newsletter is already getting pretty lengthy, so I’m going to link both Notices here and here.

Both notices are full of some pretty damning visual evidence, like this:

That’s Greg Bovino, the head of Border Patrol, tossing out a canister of tear gas while all the troops around him have their guns pointed at the ground. Get your popcorn ready, and let’s hope we get a public access line for this hearing on Tuesday.

Trump cares about this stupid ballroom more than he’s cared about anything else

The stories coming out about this stupid ballroom are incredible, and I mean “incredible” in the “I can’t believe this is real and happening to us in America” way. Last week, I wrote about how big this dumbass ballroom is going to be (twice as big as the White House), how Trump knocking down the East Wing, traditionally the realm of the First Ladies, was a little too on the nose, metaphorically, even for me, and that the ballroom is Trump’s “highest priority” right now.

But look at this reporting from the Wall St. Journal (sorry, no subscription here):

It would be great if Trump were this involved in, say, keeping SNAP benefits going, solving the shutdown crisis, or figuring out how to keep us all from going bankrupt due to his tariffs. But no. Real estate and building are things he understands, as opposed to, you know, the US Constitution, how a government functions, or literally any executive order his staff puts in front of him to sign.

And you know he’s just going to order everything to be covered in gold leaf (I’m still convinced that stuff in the Oval Office is from Home Depot and just spray-painted gold) and make it as hideous as possible.

The High Note

Each Day, I do my best to leave you with a smile on your face, a song in your heart, and the will to fight another day.

I’m very excited to see Deliver Me From Nowhere, the Bruce Springsteen biopic starring Jeremy Allen White, in no small part because our boy Carmy here appears to have kiiiiiillllled the vocals.

Check out the first 30 seconds:

And because it’s stuck in my head now, here’s a fantastic video of Thunder Road.

Survive and advance out there today, kids. Don’t let the bastards get you down.