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TRUMP, BORDER PATROL RETREAT IN FAILURE FROM CHICAGO  
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Garrett Graff
November 17, 2025
Doomsday Scenario
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_ Five important lessons of the first six months of Trump’s
immigration raids — and why CBP’s Greg Bovino is the Nathan
Bedford Forrest of the Trump era. _

Border Patrol Cmdr. Gregory Bovino prepares to drive away in his
vehicle after exiting the Dirksen U.S. Courthouse in Chicago Oct 28,
2025., (Antonio Perez/Chicago Tribune)

 

In the last few days, roving Border Patrol commander Greg Bovino
decamped from Chicago, where his military-style raids have terrorized
that community for weeks, for Charlotte, North Carolina — a somewhat
inexplicable new target (more on that below) — and a move that
underscores what has to be the growing conclusion of the now
six-month-old campaign of “acting president
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Stephen Miller to turbocharge immigration enforcement: _It’s
failing_. _Bigly._

The Border Patrol retreated from Chicago in defeat, not victory.

Writing about the Border Patrol a decade ago, I referred
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to it as a “fiercely independent agency—part police force, part
occupying army, part frontier cavalry,” and watching Bovino’s
tactics, I’ve come to believe the analogy has even more truth in the
current moment.

Bovino is basically leading a rebel cavalry, a la Confederate Gen.
Nathan Bedford Forrest, who raided and terrorized communities in
Kentucky and Tennessee in the Civil War. That latter analogy holds up
particularly well in one specific respect: Forrest became the first
Grand Wizard of the Ku Klux Klan after the war. In many ways, in fact,
Bovino’s shock troops have the most in common with the Klan “night
rides
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of the Reconstruction and Jim Crow era South, where hooded Klan
members on horseback — often “respectable” leaders of the White
community like the local sheriff — terrorized Black families and
abused their civil rights. Bovino seems focused on becoming the Nathan
Bedford Forrest of the Trump immigration era, complete with the
blatant racism, illegal tactics, and ignominious losing place in
history.

_Forrest remains a hero of the Lost Cause (Wikimedia Commons)_

Today, Bovino is leading a mounted raiding unit that descends,
unwanted, on targeted communities, terrorizes the residents, and then
— unable to break and defeat the hostile residents and
ill-positioned to fight a sustained losing battle — withdraws,
always trying to stay just a couple steps ahead of the judicial orders
and court showdowns that have blocked its worst tactics. We’ve seen
this pattern now unfold in Los Angeles, Portland, Chicago, and now
Charlotte, as well as smaller raids in places like Sacramento, and
Bovino’s force has been defeated in each of them. There’s a
national trail of court orders left behind in each jurisdiction
finding and enjoining their tactics as illegal, unnecessary, and
overly violent. In neighborhood after neighborhood, they face
resistance and then, literally, pop tear gas canisters and retreat.

In fact, while the trauma and terror that Bovino’s unit instills is
certainly real and damaging, it’s remarkable to note how
_ineffective_ the force has turned out to be. Time and again, these
agents — and the broader DHS and White House policies behind it —
are being exposed not for their strength, but their weakness. Ordinary
Americas are stronger — braver _and_ better.

Here are five important conclusions we can better understand now, six
months into the increasingly aggressive immigration enforcement
efforts nationwide:

1. TRUMP AND BOVINO FACE DIMINISHING HALF-LIVES.

Bovino’s Border Patrol raiders have one playbook — terror — and
it’s less effective each time they deploy it. So far, it’s aging
in nuclear half-lives. The shock value is wearing off and, in fact,
the targeted communities are fighting back faster and with a more
tried-and-true playbook: _Organize quickly_, _step up and document the
abuses, protest loudly, and fight in the courtrooms_
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There’s now an established (and tested) legal playbook to go after
CBP’s worst tactics; community members are finding that fighting
back against the Border Patrol works, and it’s emboldening even more
community members to take stands, even at risk of personal harm.
Chicago’s legal strategy built on lessons learned (and even the same
witnesses) from Los Angeles and other cities have faced Bovino before
— and now their lessons can be applied in Chicago.

Again, none of this is to downplay the legit terror that the masked,
military-style Border Patrol raids have inflicted on these
communities. “Kids were tear gassed on their way to celebrate
Halloween in their local school parking lot,” Judge Sara Ellis said
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in Chicago. “These kids, you can imagine, their sense of safety was
shattered ... and it’s gonna take a long time for that to come back,
if ever.” We can’t forget, downplay, or minimize any of that.
Going forward, we must do everything we can to hold Bovino and other
DHS leaders legally and criminally accountable for their actions and
betrayal of the nation’s trust. But we also can’t afford to make
these efforts seem unstoppable or ten-feet-tall. Chicago resisted
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with everything they could, and it worked:

Bovino’s night-riding cavalry turn out to be, in fact, quite
stoppable, which brings us to:

2. THE POLITICS AREN’T WORKING.

What makes Charlotte such an interesting new target is that North
Carolina is a purple state — home, in fact, to one of the most
important Senate races of 2026, as GOP senator Thom Tillis retires —
and the politics on the ground are almost certainly going to be
terrible for Republicans.

Why Charlotte in the first place? The administration doesn’t have a
good rationale. My own theory is that they’re targeting Charlotte
because it was the target of much right-wing media attention in August
when a mentally ill man, with a long criminal record, stabbed and
murdered a 23-year-old Ukrainian refugee, Iryna Zarutska
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on a public transit bus. (There’s also a sheriff in Charlotte who
famously refuses to cooperate with ICE
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Which is to say that in some twisted way, the Trump administration’s
crackdown on “illegal alien criminals” has merged with its attack
on “out-of-control crime in Blue cities” in a bastardized message
where it’s now targeting a city where an actual immigrant was killed
by an _American_. (It goes without saying that, like in many urban
areas, crime in Charlotte is actually down significantly
year-over-year — homicides alone are down 24 percent this year.)

While there’s a certain amount of firing-up-the-base and
feeding-the-right-wing-outrage-machine that Bovino’s raids
accomplish, overall the immigration raids are motivating Democrats,
empowering state leaders who criticize them, and — in North Carolina
— even turning faith communities against the GOP. Swing voters and
independents hate the raids
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which brings us to:

3. THE DATA SHOWS TRUMP’S LIES — THESE AREN’T THE WORST OF THE
WORST.

We’re getting a picture of how ineffectual these high-profile
operations are: Across Operation MIDWAY BLITZ in Chicago, it appears
that ICE and CBP arrested somewhere north of 3,300 people
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— a shockingly small number for a huge, expensive weeks-long
operation.

We may never fully know the cost of MIDWAY BLITZ, which lasted just
about two months, but it was surely tens of millions of dollars —
probably millions of dollars a day, in fact — and in the most
concentrated and violent set of raids over the better part of two
months, the Trump administration managed to arrest roughly the number
of people it hopes to arrest and deport every single day across the
nation. These are PR stunts — not a serious strategy. The terror is
real; the impact is a rounding error. That means that it’s going to
be really hard to scale or sustain this level of terror across the
country. To me, one of the interesting questions is that these
operations are so resource intensive and ultimately unsustainable,
even with the huge funding being thrown to ICE and CBP, that I wonder
whether they will actually undermine CBP’s effectiveness over time
— not to mention turn CBP and ICE into a politically toxic employer
for all but the least qualified and most racist
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Most of all, the data shows that all of the Trump administration’s
“we’re arresting the worst of the worst” isn’t reality at all.
Of 614 people included in a recent court order
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just 16 of them — roughly two percent — had a meaningful existing
criminal record. Those 16 — just _sixteen_! — included five with
domestic battery charges, two drunken driving records, one narcotics
convictions, and five who faced other battery charges, two of which
involved guns, and one person who is said to have a criminal history
in some country overseas. Just one was deemed a “national security
risk” and “no one had any convictions for murder or rape,” the
_Chicago Tribune_ reported. The local police in a city like Chicago or
D.C. surely arrest more serious criminals in run-of-the-mill
encounters across a single weekend than CBP and ICE managed to round
up in weeks.

The other 598 people had no existing criminal record, which brings us
to:

4. MOST OF THE ARRESTS ARE BEING ROUNDED UP IN “KAVANAUGH STOPS
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Earlier this year, Supreme Court Justice Brett Kavanaugh beclowned
himself enabling and allowing ICE and CBP to make stops based on
nothing more than racial profiling — explicitly endorsing and
allowing what Justice Sonia Sotomayor called a new “second-class
citizenship,” where brown people now face the presumption of guilt
on the streets rather than the presumption of innocence about their
citizenship status. He described said stops in even-then-laughable
terms:

_The Government sometimes makes brief investigative stops to check the
immigration status of those who gather in locations where people are
hired for day jobs; who work or appear to work in jobs such as
construction, landscaping, agriculture, or car washes that often do
not require paperwork and are therefore attractive to illegal
immigrants; and who do not speak much if any English. If the officers
learn that the individual they stopped is a U. S. citizen or otherwise
lawfully in the United States, they promptly let the individual go. If
the individual is illegally in the United States, the officers may
arrest the individual and initiate the process for removal._

In Charlotte, we got another window and reminder about how those
“Kavanaugh stops” play out in reality: A Honduran-born US citizen
who possessed a valid “REAL ID” had his truck window smashed by
the Border Patrol and he was hauled out and thrown to the ground
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And then, ultimately, he was released because he was, you know, an
actual US citizen. The insane thing is this was the second time he’d
been stopped by immigration agents
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— so clearly they’re relying just on him being a brown person out
in the world to stop and assault him.

They don’t know who they’re stopping, and they’re moving too
fast and unsophisticatedly to bother trying to figure out the real
“worst of the worst.” This is a clown show with tear gas — not a
serious law enforcement operation.

So far, Bovino’s cavalry raiders are bragging about detaining 81
people in and around Charlotte. As Mark Jerrell, the chair of the
Mecklenburg County Commission, said when I was on CNN this morning
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discussing this, “We don’t know who these 81 people are,” but
there’s every reason to believe that the vast majority of those 81
people are based on a high level of profiling, rather than any
targeted enforcement actions against serious criminals, which brings
us to a final important conclusion:

5. OPERATION CHARLOTTE’S WEB IS HORRID, AHISTORICAL, AND
ANTI-AMERICAN. 

E.B. White has been a hugely important influence in my life; he and my
grandfather, also a writer, kept up a charming correspondence about
the vagaries and absurdities of rural life, and I was raised on STUART
LITTLE, TRUMPET OF THE SWAN, and CHARLOTTE’S WEB as a child and came
more recently to deeply appreciate and rely upon his writing for the
_New Yorker_ and even on nuclear war
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which he so wisely challenged early on.

Please take a few minutes today to go read Chris Geidner’s essay on
why E.B. White would have so hated DHS naming its Charlotte operation
after his most famous and beloved children’s book
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Every so often I read an essay that every fiber of my being wishes I
wrote myself; Chris managed to do that last night. E.B. White was one
of the great, clear-eyed writers against fascism in the 20th century
and stood for, politically, everything that the current immigration
raids are not.

We need more E.B. Whites in this moment now.

All told, months into Bovino’s raid, it’s increasingly clear that
his efforts would be a farce — except for the very real trauma being
inflicted on lots of innocent Americans by their own
government. Nevertheless, it’s important to realize they’re
_losing_ — not winning. History and the American people are not on
their side.

_Reporting and thoughts from Garrett M. Graff, trying to answer if
things are as bad as they seem._

 

* ICE Raids
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* chicago
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* Government Failure
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