Is Chicago “A Hellhole”? The President Thinks So
- andreasachs1
- Oct 17
- 4 min read
Updated: Oct 18
By Larry Bogrow / Chicago
Following Trump's aggressive anti-immigration moves, Chicago has erupted in protests
A few days ago, my cell phone rang with a call from an old friend in Phoenix. At least it wasn’t another spam call like the ones that I receive on a daily basis.
“Hi, Larry. How the heck are you doing lately?”
“Fine, thanks Ken. How about you and Mary?” More pleasantries followed, until the main reason for his call became clear. Here’s how our conversation went . . .
Ken: It seems like things are crazy in Chicago. How goes it? Is it safe?
Me: Well, you can’t believe everything you hear these days.
That’s when I had to read Ken a recent quote from our president: “There’s no place, there’s no place in the world, including you can go to Afghanistan. You can go to places that you would think of, they don’t even come close to this. Chicago is a hellhole right now.”
Ken: Unbelievable! I hadn’t heard that. How bad is it?
Me: I know there are some problems with ICE that are in isolated parts of Chicago, yet the areas seem to be expanding. Coincidentally, just a few days ago I saw an article in the Chicago Tribune that read: “Chicago Did It–Again! Chicago has been voted best big city in the U.S. by Conde’ Nast Traveler readers for a record-breaking nine years in a row. This city is truly never done, never outdone!” How’s that for irony?
Ken: Don’t most Chicagoans feel safe and have confidence that the federal government is handling the situation properly?
Me: Some might feel that way and most want to feel that way, but what we’re seeing and experiencing is anything but faith and confidence that the Trump administration is doing the right things. Pretty sad commentary, isn’t it?
Ken: What can you tell me about ICE and the deployment of federal troops?
Me: I can tell you that ICE has set up a holding facility in west suburban Broadview, which has been the site since of multiple anti-immigration enforcement demonstrations. It’s where masked federal agents, with no badges who wear homemade uniforms, have been hurling tear gas and baton rounds at protesters. So far, federal agents have made more than 800 arrests in the Chicago area. While the Trump administration claims to be targeting “the worst of the worst,” many of the detainees have no criminal record. That’s criminal in itself!
Ken: But why was the National Guard called in? Are they visible on the streets of Chicago?
Me: Because there has been a surge of violence and unrest due to the ramped-up federal immigration enforcement in recent weeks. There are currently over 200 National Guard troops from Texas and 300 members from Illinois who have all been federalized and are currently at a U.S. Army reserve training center in southwest suburban Elwood. The troops are supposedly needed to protect the ICE and border patrol agents. This is Trump’s response to the “increasingly heated immigration crackdown protests.” As of today (10/17)), National Guard troops are not on the streets of Chicago due to decisions by the federal courts that block troops from duty assisting with immigration enforcement activities. But this could only be a temporary win.
Ken: Hasn't your governor, JB Ptitzker, been a critic of Donald Trump?
Me: Yes, Gov. Pritzker has been a very vocal critic of the president and his administration. Only three days ago, the governor said, “This is a man who’s suffering from dementia. This is a man who has something stuck in his head. He can’t get it out of his head. He doesn’t read. He doesn’t know anything that’s up to date. It’s just something in the recesses of his brain that is effectuating to have him call out these cities. And then, unfortunately, he has the power of the military, the power of the federal government to do his bidding and that’s what he’s doing.”
Ken: Didn’t President Trump reply to those harsh words?
Me: What do you think? Of course, he did by saying that Mayor Brandon Johnson and Gov. Pritzker should both be jailed for failing to protect ICE officers. The war of words continued when the governor called the president “unhinged and a wannabe dictator.” Mayor Johnson later stated on CNN that Trump is “unstable and a double-minded individual who is a threat to democracy.”
Ken: You sure don’t seem to like our president and what’s happening in Chicago.
Me: No, not at all. That’s because our country has never been more divided. Even a Civil War seems possible. Every day brings other news and announcements from our president that worry and scare me. What about our kids, our grandkids and the future of our country and democracy?
Ken: Hey Larry, I thought I was the one asking the questions! How about closing on a lighter note?
Me: OK, Ken. Sorry for getting carried away. Did you hear Trump’s speech to the UN recently when he said he helped end seven wars? One he saved was between Azerbaijan and Albania, which happen to be over 1,800 miles apart. He meant to say, Armenia, but we can excuse his lack of geographic knowledge, can’t we? We here in Chicago look forward to President Trump’s next visit to the Windy City . . . because our escalators and teleprompters are all in excellent working order!
Ken: Funny! I gotta go, Lar.
Me: Thanks for calling, Ken. Let’s hope for peace, nonviolence and a return to democracy!

Former Detroiter Larry Bogrow is a retired marketing and advertising executive. He and his wife Sue, who is orginally from Windsor, Ontario, have been married for 51 years and reside in Chicago‘s northwest suburbs (Mundelein, to be exact) in a Del Webb active adult community. Larry has been an avid pickleball enthusiast for over 15 years and does much volunteering in his community, including writing articles in its quarterly newsletters. He’s also a self-proclaimed Seinfeld trivia buff.









Great article Larry. It is so sad that we have to monitor our thoughts when catching up with old friends, but that is what has happened in our country thanks to the two Trump administrations. As a relatively new Illinois resident, I do think that Chicago is a very troubled city, however the current occupation by ICE has done nothing but exacerbate the situation. In fact these agents seem to cause far more issues than they address. Trump's behavior has unleashed a sense of entitlement by the already crass population and has given new meaning to the term 'Ugly American". Whenall is said and done I fear that it will take decades to reverse the mess that Trump has brought…
Thanks for sharing the enjoyable article. Loved it!
As for me, I have stopped watching the general news. The only news I am following is business news. Even there, I thought that “Market Based Economy “ and “Democracy “ won the Cold War in 1991. Trump is essentially saying that isn’t so! We have to follow the “Chinese Communist Economy “ and the government should be investing in the market and private companies! How far are we from a”Banana Republic “ I don’t know. Pray for our Grandchildren!
Larry, Thanks for sharing your article and exchange with your friend, Ken. It’s very disturbing to see and hear what’s happening in beautiful cities like Chicago. I have relatives there, as well. Only Democrat cities where ice and the guard are being dispatched, and totally different from reality. It’s very upsetting to see this taking place in America… and sadder to see how many elected officials lack the spine and courage to speak up and out . Thanks for sharing your thoughts, and be well…. Plus, greetings from Oak Park- Jerry N.