The Trump Show came to Chicago today. The Orange One took part in a Q & A session as part of the National Association of Black Journalists annual convention. His inquisitors were three respected Black women journalists. What could possibly go wrong? From the moment the 32-minute session began, the fireworks exploded.

The Q & A. Speaking of Vice-President Kamala Harris, Trump said, “She was Indian all the way, and then all of a sudden she made a turn and she became a Black person.” As November comes into sharper focus following the change at the top of the ticket that saw President Biden step aside, Harris, if she can tack toward the center, should prevail. Trump seems to be self-immolating. As his talk gets crazier—’weird’ is now the new catchphrase—I suspect many ‘double haters’ and others who are not diehard MAGAs will wretch at the prospect of four more years of Trump.

The Streets: 56 Years Ago. As usual, I was on the streets both before and during Trump’s session with the Black journalists. Looking up at the cavernous brick building that is the Hilton, I was immediately taken back to the summer between 7th and 8th grades. Yes, I vividly remember watching the 1968 Democratic National Convention—Mayor Daley mouthing “Fuck You, you Jew son a bitch” after Senator Abraham Ribicoff, speaking from the podium, said “And with George McGovern as president of the United States, we wouldn’t have to have Gestapo tactics in the streets of Chicago . . . With George McGovern we wouldn’t have the National Guard.” I vividly recall the images of Chicago Police officers and National Guard troops beating demonstrators senseless in Grant Park as large clouds of tear gas rose from the pavement, partially obscuring what was happening; the bloody people—we still had a black and white television—being attended to by medics; and the chaos methodically unfolding below the windows of the same building I was looking up at today. After living in Chicago for 31 years, I still recall that imagery everytime I pass the Hilton.

The Streets: Will There Be A Repeat Performance? The question that has hovered over the city for months is whether 2024 will see a repeat of 1968. After spending time on the street in Milwaukee during the Republican National Convention earlier this month, I doubt it for several reasons. First, the Department of Homeland was particularly adept in securing the convention hall, relying on the deployment of checkpoints, concrete barriers, metal fencing, and police departments who came from around the country. Chicago will benefit from similar measures.

Second, the police are much better trained in dealing with crowds and mobs. I have no doubt that there will be police in riot gear, military vehicles, and horses, but I suspect they will be kept out of sight. As a former Chicago Police Department superintendent recently said, paraphrasing, “If you don’t want a riot, don’t dress for a riot.”

Third, despite all the talk of a large counter-demonstration in Milwaukee, the turnout was pathetic. The organizers boasted that at least 5,000 people would demonstrate. Not the case; maybe 1,000. Whether the size of the demonstrations in Chicago will fall short of the projected tens of thousands is unclear. The pro-Palestinian forces have turned out 8,000 to 9,000 for several demonstrations. Behind Enemy Lines and other Left groups have been planning for over a year, but I just haven’t seen large numbers materialize over the last several months at Left-leaning demonstrations.

This past weekend, I saw a video from a street demonstration organized by one of the Leftist groups as part of their neighborhood outreach program. There were maybe ten people pictured. I would not be posting that sort of evidence on Instagram if I were this group.

I spoke briefly with two CPD officials today. As usual both were tight-lipped, but both had been in Milwaukee during the RNC. I sensed both were somewhat relieved given the poor turnout. Maybe “hopeful” is the better word. Contrary to what many demonstrators believe, CPD simply wants a week where everyone is safe, and those who want to express their opinion can do so peacefully. Despite a few people bent on trouble, most of the demonstrators that I have encountered share that view.

The Streets: Grant Park Today. Today’s anti-Trump rally across from the Hilton serves as a perfect example. In fairness, today is a workday and the organizers had no more than two days advance notice. Yet, I can make the case that there were more members of the media present than demonstrators. At most, there were 100 to 150 demonstrators, and that is being generous. If Trump doesn’t bring the Left out in droves, I have trouble viewing the Democrats as a more enticing target, particularly now that “Genocide Joe” is out of the race. Candidate Harris should be far more appealing given her more favorable predisposition toward the Palestinians, which makes me wonder why the pro-Palestinian forces still hope to embarrass the Democrats in Chicago. Do they believe that Trump will be better for the Palestinians than Harris? Some of the hardline Palestines in the Detroit area are already softening their opposition to the Democratic presidential candidate.

As I circulated through today’s crowd, one word came to mind, “ragtag.” In the mix were a couple of people preaching the Gospel. One was disturbed by the level of anger and hostility in the crowd. He told me that if the demonstrators just believe in God and his infinite knowledge, they would be much happier and secure people.

A group brought tubas and other brass instruments, providing a soundtrack meant to ward off “Hate” and “Aggression.” Operating under the moniker SAHBRA—Sousaphones Against Hate And Baritones Resisting Aggression—their performance was hit and miss, but I will keep an eye out for them during the DNC marches.

People from the U.S. Palestinian Network showed up, making sure that the plight of the Palestinians received sufficient voice. Kobi Guillory, from the Chicago Alliance Against Racist and Political Repression, led many of the chants throughout the day. While Guillory focus on a number of issues, he and his group have become Palestinian allies.

Several Harris supporters were visible, hoping to taunt Trump. Some circulated among the anti-Trump demonstrators standing in Grant Park across from the Hilton.

The only time I saw any potential for violence was shortly after I arrived. A man in a red shirt was upset that the demonstrators were making noise. According to his sensibilities, they were showing disrespect for the former president. Another man kept challenging him. At times, I thought they would come to blows, particularly when the guy in the red shirt wanted the other guy to follow him down the street (presumably to settle matters). Fortunately, both kept their emotions in check, but the heat turned up each time they got within arms-length of each other.

Those on the Left chanted, and several speakers used a portable sound system, but when all was said and done, their effort was lame. They showed the flag, but not much else. The heat and humidity probably accounts in part for the overall flaccid effort. People were wilting.

One demonstrator was particularly notable because he kept bellowing out the word “Loser.” He sounded more like a sick moose than a demonstrator. I had to ask someone whether he was casting aspersions on Trump or the Leftists. I am still not certain, but he proved to be very annoying, and not just to me.

At one point, he complained that the photojournalists would use images of him out of context, making him look like an idiot. Even in context, he looked and sounded like an obnoxious idiot. Tip for Demonstrators: if you don’t want to be portrayed as an idiot, don’t act like one.

The Street: Security. As for Trump, I never saw his motorcade. I assume it arrived on the Wabash side of the Hilton, entering a protected loading area encased in the Hilton’s massive structure.

I was surprised by the level of security on Michigan Avenue, which struck me as light, particularly given the much higher police presence during three Biden fundraisers earlier this year and late last year. There were about 20 bicycle cops ‘minding’ the demonstrators, with 30 or 40 uniform officers spread out on traffic islands and in front of the hotel. On Balbo, adjacent to the Hilton on its northside, and East 8th Street, adjacent to the Hilton on its southside, the police had positioned their SUVs and other assets. I saw no Secret Service or Homeland Security officers—they were undoubtedly present.

I suspect the security people must have been pleased with the location. The Secret Service most likely moved Trump through the Hilton outside of public sight-lines. Most likely, he rode a service elevator to the ballroom, and retraced his steps when he left. Given the Hilton’s close proximity to Soldier Field, Trump probably rode a helicopter from O’Hare to a landing space adjacent to stadium; followed by quick limo ride to the Hilton. I didn’t notice any road closures, but some CTA buses were rerouted.

The Street: Afterwards. I did not stay until the bitter end—it was too hot and there was nothing happening. How many photographs can you make of 100 or so people milling about. Looking for something to drink, I headed north. This being Chicago, I encountered two happenings outside the Art Institute. One was a fashion shoot with two attractive women surrounded by four men in nothing but their Calvin Klein undies.

The second was a Catholic group demonstrating against the grooming of children, with a focus on members of the LGBTQ Community. I asked one of the demonstrators whether any members of the group had been molested by a Catholic priest—a potentially antagonistic question, but it was not my intent to antagonize. He said, “No,” and then pointed out that pedophilic priests go to Hell. Good to know.

I eventually found a cold drink and an air conditioned cafe, permitting me to read about Trump’s disastrous Q & A session.

[Click on an Image to Enlarge It. The Images Are Not Necessarily in Exact Chronological Order]

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