The homelessness executive order was signed by Donald Trump in July 2025, and John Kiriakou discussed it the day it was reported.
The numbers
The order “actually understates the problem,” Kiriakou says. “It says that there’s 250,000 homeless people in the United States. They’re actually 770,000.” The figure had sat at 550,000 for years and “shot up” over the four years since COVID as prices rose and people were priced out of housing — and none of it “counting the millions who are couch surfing, hidden homeless.”[1][2]
On the stated motive he is unsparing but does not dispute the observation. Trump “said it’s a bad look in DC for foreign dignitaries to see tent cities as they drive in from Reagan airport” — and, Kiriakou allows, “he’s right” that nobody wants to see what he describes. What he draws from it is a different lesson: “that’s capitalism, and you can’t keep cutting the budget and starting with services.”[2][3]
Diagnosis and cure
Kiriakou separates Trump’s grasp of a problem from his answer to it, and gives him the first. Trump is “really good at diagnosing problems” — Midwestern factories closed, nobody retrained, people poor and depressed and addicted to opiates — and “honestly, that is not a small thing. Being able to diagnose the problem is very, very important.” He adds that he did not see Joe Biden or Kamala Harris doing it.[3][4]
The cure is where he parts company: “Trump’s very bad at coming up with the cure and the treatment.” The order’s thesis — that most publicly homeless people are mentally ill, emotionally disturbed, addicted, or some combination — he accepts as “probably true”, adding that those who are not so when they reach the street “rapidly deteriorate.”[4]
The missing facilities
The remedy the order reaches for is forcible commitment, and Kiriakou’s objection is practical rather than civil-libertarian. He explicitly refuses the position that a person has a moral and legal right to sleep outside in Manhattan at five below zero: he wants them “picked up, dragged off and taken somewhere” — “but I want them taken somewhere safe and nice and warm”, not abused, humiliated or attacked.[5][6]
The problem is that the somewhere does not exist. “There are no facilities, right? Where are you going to put them?” He calls it the same hole that swallows mass deportation — “there’s no facilities to handle the mass deportations. There’s no facilities to handle the mass removal of the homeless from American city streets” — and says it “goes double for drug addiction. There’s no treatment really available. There’s no services available.”[6][7]
He leaves the condition on which he would change his mind on the record: “If you want to create a massive infrastructure, a massive safety net to deal with these people, God bless you and I will help you and I will support you and I will scream it to the heavens. What a great president you are. But I don’t see that happening.”[7][8]
What he would accept instead
A further limit is jurisdictional. Homelessness is a state matter; a president may fiddle with what little federal funding exists, but there is nothing he can do to force tent cities to be cleared or people into institutions. On that reading the order is “mostly talk.”[9]
The one proposal Kiriakou says would be “something else” is a conversion rather than a compulsion: taking abandoned or mothballed military bases and turning them into housing for the homeless, “where maybe they can undergo some job training, get mental health care, whatever, and then be reintroduced into society.”[10]