Joe Trippi Should Wear the Jacket

By Pat Hickey

May 5th, 2023

“Losing would be painful, but not as painful as knowing there was something else you could’ve done.” – Joe Trippi

Ten days after Democrat consultant Joe Trippi handed Chicago over to the Chicago Teachers Union and Brandon Johnson, I attended The Monterey Jazz Festival at Chicago’s Symphony Center. Kurt Elling and the magnificent Veronica Swift fronted four wildly talented musicians for a two-hour taste of the California fest. 

We arrived twenty minutes before the doors opened to the evening’s patrons. Located at 220 South Michigan Avenue, Symphony Center (formerly Theodore Thomas Orchestra Hall) had been my home and place of employment from 1968 through 1974. In high school, I worked summers at the home of the greatest symphony orchestra on earth and when I attended Loyola University, I practically lived there working 3 PM to midnight and midnight. Whenever the symphony played, or featured acts from impresario Harry Seltzer there was a thick Chicago Police presence on Michigan Avenue. Two or three patrolmen between Jackson and Adams, as well as motorcycle police officers and more than a few white shirts, police brass. 

Not so, in 2023. I remarked to the lovely lady who joined me for the evening, ” Jesus there is only one cop out here and he is walking north.”  Former Mayor Lori Lightfoot’s war on law enforcement was in full fruition. 

The Loop looks ugly (dirty diapers dot Adams and Wabash) rubbish everywhere and knots of angry looking young men dominate the Divvy racks. This is a place to avoid. Chicago is done. We left Symphony Center after the wonderful show, locked the doors and made our way to The Ike and on to Forest Park. The next day I needed to return to Michigan City and deposit my tuxedo from Louie’s Tux. 

On Saturday, I heard of and later watched news coverage of the teen takeover of Millennium Park and Michigan Avenue. The young people were savages. Obviously, Chicago Public Schools have created a latter-day Red Guard to pummel the middle class. Riot where the money is. Right out of the Bill Ayers playbook! Give him his props. He did more to mesmerize our teachers than old Horace Mann. 

Lori Lightfoot is out, Brandon Johnson is in, and Chicago is finished. 

Thank Joe Trippi.  Paul Vallas will wear the jacket for this loss and the subsequent tumults du jour, but someone asked Joe Trippi to run the Vallas campaign. Who suggested Joe Trippi, the man who sent the screamer Howard Dean into oblivion? It was someone who wanted to please Cook County President Toni Preckwinkle. 

She has no fingerprints on this, but I must believe it to be so. Toni Preckwinkle wields great power and remains a humorless racist with a penchant for political torture. It was Toni Preckwinkle who might have uttered, “Will no one rid me of this troublesome geek (policy wonk)?”  One of Toni’s barons must have decided to do the old Thomas Becket on Paul Vallas. The broadsword used to hack Paul Vallas was California Techno-politico Joe Trippi.

Who brought this guy into the Vallas campaign?

When Paul Vallas announced Team Trippi, back in September of 2022, I thought that Lightfoot had so badly screwed up the city of Chicago, as well as the City of Chicago, that Paul Vallas would be unbeatable. More fool I. 

Let’s remember who calls the shots. None other than Toni Preckwinkle and there was no way in Hell that Paul Vallas would replace the foul-mouthed cartoon character on the 5th Floor of Toni’s City Hall.

Chicago is the city of the take, and nothing is on the Square. 

Joe Trippi, I believe, was brought in to scuttle any chance Paul Vallas might have had to save Chicago and scuttle it he did! The same guy who pushed Howard “the Scream” Dean into political obscurity would work his Progressive magic on Policy Wonk Paul. 

The evidence is clear. On February 17th, only days before the primary election Paul Vallas issued this statement condemning the FOP that had endorsed him and the Governor of Florida, Ron De Santis, who has taken the same anti-crime position as Vallas:  “I am disappointed in FOP leadership for inviting him to speak to officers. DeSantis’ record of trying to erase the LGBTQ community, banning books on Black History and much more is not in line with my values, the values of our community, or the values of the rank-and-file police officers who I believe have no interest in getting swept up in culture wars and national Republican Party politics,” 

Ain’t no way Paul Vallas wrote that. That is pure Joe Trippi. Vallas committed an unforced error by putting his name to this statement. He was not a guest of the event sponsored by the law enforcement officers who backed his run for mayor long before any other labor union, or civic group. Paul Vallas allowed the opposition to define him. 

Joe Trippi saw that. Joe Trippi and pollster Mark Mellman, a Pat Quinn operative, poisoned any chance of non-Progressive Democrats, much less Republicans of voting for Paul Vallas. The Progressives killed the Vallas Campaign.

Listen to Trippi on Primary night. 

Progressive this and Progressive that. Paul Vallas is a Progressive, I guess, and that will turn off voters like me. I think that it did. While Paul Vallas dominated the primary, a good chunk of Vallas voters stayed home for the run-off. 

Paul Vallas allowed Trippi to define him. Would it not make sense to embrace every available vote and ensure that it stays with you? No, Joe Trippi wants to “build trust between communities.” and kick away every vote that just might not want anything to do with progressive. Lori Lightfoot, Chuy Garcia and Brandon Johnson are Progressives. Progressive Pat Quinn endorsed Vallas late in the game. The most polarizing Illinois Governor in history gave Quinn the job and he was one one-half and done. 

Paul Vallas is not a MAGA anything, but he allows the progressive to paint him so. Ron DeSantis had nothing to do with the Chicago mayoral race, but Joe Trippi, I believe, forced Paul Vallas’s hand onto the statement that also condemned the FOP.

Paul Vallas helped knock Lori Lightfoot out of City Hall, but Joe Trippi ensured that Marxist Progressive Brandon Johnson will do the bidding of Cook County Boss Toni Preckwinkle. 

I am from Chicago. I loved Chicago. Could not live there anymore and do not. I live in the great State of Indiana. 

I am not political operative, but I remember how a city should be lead. Not by polls, or internet gizmos, but by thoughtful people who value our American way of life cherish liberty more than “getting on the popular side of an issue.”  People need character to lead, not political spin doctors.

I know about Joe Trippi. He is the internet wiz who skyrocketed Howard Dean in the popular imagination and then corkscrewed Dean into the political loam. Joe Trippi works with Lincoln Project,  dedicated to Democrats as Republicans who hate Trump. Like Catholics for Abortion. Now, that is certainly Progressive. Joe Trippi does not fail. His candidates do. 

“FOP is Maga. Trump is Maga. FOP endorsed Vallas. Ergo, Vallas is Maga and Trumpilicious!” What would the Old Rail-splitter think of that logic? Not much. It works for The New York Times, NPR and WTTW. 

Police officers are targets. They know that. The Progressives hate police officers and coddle criminals. 

I know Paul Vallas, as he was my friend and neighbor in Morgan Park of Chicago for 23 years. He is dead-on honest, generous and thoughtful. I found it odd that Paul did not identify Morgan Park as a place where he once lived – he mentioned Roseland and Bridgeport. Too many police officers in Morgan Park, for Joe Trippi and Mark Mellman?

I spoke with a friend who is very politically hep, and he told me, ” Trippi and Mellman did not want any national attention for Paul Vallas, as his character and program of fighting crime runs counter to Progressive norms. They wanted no national focus on Vallas, or the Chicago mayor’s race.” 

After the April 4th  run-off defeat, Joe Trippi said this,  “Obviously there’s a spirited debate, and a split, in this city at least, about what direction to go in.”

“I’m not sure you can take what happened here and extrapolate it to Los Angeles or other big cities,” Trippi said. “Chicago and Illinois are going to vote for Biden. Half of Chicago was [willing to embrace Johnson], but that doesn’t tell you anything about anywhere else.”  Until mid-April when mobs of CPS educated young savages destroy cars, beat people and kill most certainly does tell you something. 

Yep, Brandon Johnson’s voters will vote for Joe Biden and Chicago will flat-line. 

The night after I attended the Jazz Festival at Symphony Center Chicago defined itself as Progressive City. 

Paul Vallas might have made a great Chicago mayor. Joe Trippi saw to it that we will never know.

It is Toni Preckwinkle’s Chicago. That was the plan, it seems to me. That is the way it shall remain. 

-30-

Born November 8, 1952 in Englewood Hospital, Chicago Illinois, Pat Hickey attended Chicago Catholic grammar and high schools, received a Bachelor of Arts in English Literature from Loyola University in 1974, began teaching English and coaching sports at Bishop McNamara High School in Kankakee, IL in 1975, married Mary Cleary in 1983, received a Master of Arts in English Literature from Loyola in 1987, taught at La Lumiere School in Indiana from 1988-1994, took a position as Director of Development with Bishop Noll Institute in Hammond, IN and then Leo High School in Chicago in 1996.  His wife Mary died in 1998 and Hickey returned with his three children to Chicago’s south side. From 1998 until 2019, it became obvious that Illinois and Chicago turned like Stilton cheese on a humid countertop. In that time, he wrote a couple of books and many columns for Irish American News. When the kids became independent and vital adults, he moved to Michigan City, Indiana, where he job coaches Downs Syndrome and Autistic teens in LaPorte County.  He walks to the Michigan City Lighthouse every chance he gets.

Comments 37

  1. The very personable Harold Washington said, “Hocus, Pocus, Domino-cus”.

    The game continues. I used to refer to Chicago city hall’s cabal as “Local 13 – Thieves, Villains, & Scoundrels” (Rocky & Bullwinkle) but that joke isn’t funny anymore. The image of ward thugs in the dark basement of city hall sitting around a folding table covered with coffee cups, cigar smoke swirling in the light from the single bulb over the table is gone.

    The sinister levels of sabotage pervade the Chicago political scene and nuance is fatal within those systems. I can easily buy into the idea that Boss Toni used a shill to get Mr Trippi named as Vallas’ campaign manager. Bottom line – Joe Trippi ain’t from Chicago!

    Mr. Hickey nails it, mixing eloquence with “Sout’ Side” common sense. Someone had to say it. The city that grew under King Richard I has eroded behind the treachery of power and wealth hungry tribes. Current leader, “Queen Tony”, wears the cloak and ensured Vallas would not upset the “Good Old Pols” apple cart!

    1. Well said James Stedman. Took the words right out of my mouth if I had them. Any eloquence is leaving with age.
      What strikes me is that Vallas didn’t see Trippi for what he is. There are a lot more conservatives, MAGA supporters, Trump voters than people think (in Chicago). Apathy and political fatigue, low info voters, ignorance, have taken over.

  3. Vallas was certainly the best person to start rebuilding Chicago, but thinking he could win was just a cruel dream. He knows the details of how to run a city, but he can’t campaign with the political killers. He has too much heart, and can’t close in for the final fight. No, Chicago had no chance of turning in the right direction. The chumbalones have chosen their poison and now have no grounds to complain. Chicago will burn by its own match.

  4. My heart breaks to see what’s happened to this once safe beautiful city. After the Floyd riots I had to go into the city. I was horrified. It looked like a third world country all boarded up and damaged. That coupled with the rise in our tax bill, we sold our home and fled. And now it appears to be getting worse.

  5. I live in Chicago, travel on CTA and get angry when people write that Chicago is dead. We have big problems to address but many of us choose to stay.

    1. You have my sympathy and admiration. My brother and his wife said the same thing until front door carjackings and being literally run over in a high end department store by thieves stealing Louis Vuitton bags sent them packing.

    2. Fool. Why don’t you get on the CTA at 95th and Ryan at Midnite and ride around til dawn and let us know what you find. Assuming you survive.

    1. U r Like those who stayed in the Alamo.
      I lived in chgo when my mother could get on the cta rail in a mink coat, her large diamond wedding ring and dressed to the T and get off at Fields to shop, eat lunch take us to a movie and come home.
      Tell Geraldine, when is that coming back.

  7. Did Paul really think that his comments in the statement would not be ill received by a voting bloc that was strongly on his side. This causes me to question his political savvy. And I like the man!

  8. I was born, raised and educated in Chicago which I used to love. The Chicago I loved does not exist any more. In November I finally realized Illinois is beyond being saved and moved out of the state. In reality I did not leave Illinois as much as Illinois left me.

  9. Pat, thanks as always. Btw, I think you meant Howard Dean not John. And I’d also observe that half of Chicago did not support Mr. CTU for mayor in the runoff. 17% did. Vallas got 16%. The remaining 67% stayed home. I think you’re spot on that Vallas got defined by his runoff opponent…and those Vallas voters stayed home in droves. Such is voter apathy, resignation and cynicism in a one party system. Just shut up and take it.

  10. Like a prisoner who has tally marks on the wall, counting down the days left of his sentence, I find myself doing the same on how much longer I will stay to put up with this political nightmare of Cook County, and the State of Illinois. Thankfully, I don’t have kids in the school system anymore. Our goal was to be out in 8 more years, but not so sure my patience will last that long. I’ve lived here my entire life, I’m in the loop at least 3xs a week, the city is on life support, some of us want so desperately for the city to get up off the canvas, but the referee is getting real close to the 10 count.

  11. You’re probably right Pat. The statement was disingenuous and obviously calculated enough to scare off a few voters, and Vallas only lost by a whisker. A savvy operative wouldn’t have issued it, I’m guessing.

    The Latino vote stayed home. Where was the old Hispanic Daley Organization? They couldn’t cut some kind of deal for wrought iron fencing, landscaping services, and airport contracts? That’s why he lost.

    You’re also missing an other obvious thing Pat. Paul Vallas has the charisma of a ham sandwich. Say what you wants about him, but Harold Washington has loads of charm.so many people have given up on the rigged election process that a small group of union members and stupid young people were able to go for this inexperienced, pandering fool.

    Pail didn’t make his case to the people. He used scare tactic commercials. The media was not help either, but he could have done rally’s around the city, Trump style, and they would have had to cover him. He could have brought his vision directly to the people in the neighborhoods and give specific things he would fix, upgrade, enhance and let them know in no u certain terms that he had their back.

    He blew it, simple as thst/

  12. With each passing year, I find myself more leery of driving back to my old home city to hear the world’s greatest orchestra. How will the Chicago Symphony Orchestra deal with its location problem? As Pat Hickey notes, the audiences for great music are perfect targets for the criminal sociopaths who are now repeatedly returned to the streets by compassionate Soros Democrats.

    How about the Arlington Heights site that the Bears will be moving to? Could some Suburban Symphony Center be included in the project?

    But even that would probably be only a temporary fix. As Democrats flee the city dystopias they create, they bring their politics with them, and leftist rot spreads to the suburbs. Maybe the CSO should relocate to some farmland in Edgar County.

    1. The CSO already does concerts in the western burbs. I believe in Wheaton, ill. That could be their new home. They could spend time during season at U of Illinois, Champaign/Urbana in Kranert Hall, a nice venue. They could find a venue in the Tony North Shore also.
      As I mentioned before, the Cleveland Orchestra does or did a large number of concerts in FLORIDA during its winter season, following their wealthy snowbird retirees.
      I attend most of the CSO afternoon concerts and avoid totally the evening events. The concerts are still well attended. But I fear if the crime scares away concert goers the CSO will bolt, as they should.

  13. Here I thought Lightfoot was the winner in the city’s race to the bottom, but our socialist CTU puppet and Chicago’s very own “Let’s Go Brandon” says, “Hold my beer”.

  14. Pat, right on the money. When Paul Vallas trashed DeSantis for appearing in Elmhurst I smelled a rat, and was able to get in to see DeSantis at that rally, thanks to our mutual friend Jeanne Ives. I asked Jeanne about Vallas vilifying DeSantis, who I admire, she told me “That’s not the Paul Vallas I know”, Also right on the money. Something nefarious was taking place in Paul’s campaign, alienating the folks/cops etc. who got him there. What kind of town are we in when Republicans are likened to Nazis? That’s not America or the Chicago I grew up in. I think Paul’s embrace of Trippi and those like him was Paul trying to please everybody, an admirable trait for most human beings but not for leaders. Florida just looking better and better now.

  15. Love this column, but it raises so many questions. I wonder why Trippi was was embraced by the Vallas team to begin with. Paul does not seem to be an ignorant man. He has been around politics enough to know who Trippi is, so why include him? Choosing the wrong person within your campaign is a sign of weakness. There was zero push back on Johnson’s erroneous claims that Vallas was a MAGA wannabe. There was zero use of social media. There was zero grassroots efforts to bring young voters to his side. Didn’t Vallas have a gut feeling that these directions were wrong? Regardless of Trippi, it was still Vallas’ campaign to win or lose. That is what is so infuriating.

    1. It’s almost like he tried to lose, isn’t it. Trump has proven that you can bypass party infrastructure and media by going directly to the people, drawing a crowd and being bold.

      He should have had rally’s in every ward and pointed to infrastructure he would replace. He should have called out the corruption and proposed solutions. He should have appealed to the young

  16. Radicals…NOT…progressives. Progressive, progress means moving forward. We are definitely in a time of regressive, moving back.

    I said it before, during and after the primary/runoff. Vallas didn’t have a chance. Why ? He was the most obvious choice. Nuff said.

    As “progressives” don’t deserve their romanced title, saying the people who voted Johnson in are chumbalones is a disservice to chumbalones because they are beyond stupid and foolish. There are those out there, including some here (it should be obvious) that need to wake up and get into reality.

  17. YET ANOTHER piece about the ‘decline’ of Chicago, written by an older man who no longer lives here, written for an audience of older men who no longer live here, about an election that is over. What’s the point? I disagree with your drive by assessment of downtown. Tuesday through Thursday feels as crowded and vibrant as ever, especially now that we’ve had some nice weather. Mondays and Fridays its a relative ghost town. That is the result of hybrid work, not lawlessness. I am absolutely NOT ignoring post covid crime, but there is and will never be a political solution to a socio-economic problem. I’ll ask the same question, the real question we should be asking: “Post covid-how do we redefine large urban downtowns, knowing that the daily work crowds will likely never be what they were?” Convert office space to housing? Focus on hospitality? Convert empty office space to hybrid work centers? Don’t know. But the ‘oh boo hoo we left years ago and aren’t EVER coming back!’ story is boring. Good riddance. Stay in Florida under Emperor DeSantis rule. The rest of us will figure this out.

  18. So, it appears that the cumbolones, that either didn’t vote, or voted for Johnson, will get the government they deserve with the new Marxist Mayor. I’ll watch, at a distance, as the social workers converge on a 911 crime scene, instead of the cops! Anyone have any idea how that’ll work out? Inasmuch as nothing’s going to change, we are going to be forced to witness Chicago’s funeral. The death of a city, just like LA, Portland, SanFran, NYC, Seattle, Minneapolis…the list goes on. All dem run cities with their “progressive” agendas – along with the demise of America and her values by Joe and his family, and those “behind the scenes” that are really calling the shots! Let us pray….

  20. Yo Riga Tee! Most of us with any sense and financial means have already left Chicago. You are more than welcome to stay there with the criminals, car jackers, and
    graft. Using your vast imaginary wealth you are probably buying up prime lakefront property and numerous vacant fine dining establishments on the mag mile. Me? I escaped Dystopia and moved to Utopia a few years ago. My new home has doubled in value already. I live in a true melting pot with great neighbors of all races. We all help each other. Crime? People have left car doors unlocked and noticed sunglasses missing or a change jar emptied. Happens once in a while, but not too often. Fine dining is available nearby, not too far. We left Chicago because we were outnumbered by the stupid. The results of this election have proved my theory correct. The movie “Idiocracy” was truly prophetic. If you actually lived in Chicago (which you don’t) you are also one of these stupids. Furthur proving my theory correct. Enjoy, tip your imaginary bartender well at your imaginary rooftop bar in Beloit. Rents are going up out dere I hear….

  21. I can still recall having to stoop down to pick my jaw up off the floor when I read about Vallas dissing FOP and DiSantis. That was a huge “What the hell is going on?” moment.

  22. Great article Pat. Thanks for sharing. Chicago is truly lost. Very sad as I spent most of my adult life living there. I never liked Joe Trippi and you’ve confirmed my thoughts on him. I just hopes he runs a campaign for somebody I wish to lose. Perhaps Joe Biden.

  23. Thanks, Pat, for the insights into “what happened?!”. All makes sense. I blame Vallas for selecting this agent for his and the city’s doom. He really should have known better. It will take Chicago more time than I have left on this earth for the city once again to rise from the depths of urban hell.

  24. I disagree. Paul Vallas should wear the jacket. To paraphrase former president Truman, the buck stops with Vallas … at least it should have if he were what he was selling: the potential leader of the City of Chicago. To be sure Mr. Vallas is great at policy and wonk type stuff; so good that he would be an asset in any mayoral administration. But he is NOT the guy … he is NOT the leader. That is why he is not the Mayor. Joe Trippi is an irrelevant distraction and poor excuse for failure. Mr Vallas’ failed all by himself. His campaign proved beyond a shadow of a doubt he, and he alone is not the guy. And that is the inconvenient truth. Sad.

  25. Very sad – second time Paul was let down by fellow democrats. First in Gov. Race by Madigan and friends giving us Rod. Now this- CTU Brandon. A good man who would have started to bring City forward.

  26. Throughout his campaign I wondered when is he going to hammer Johnson as a key member of the CTU leadership that kept your kids out of school and falling behind, while the parochial and private schools flourished. Now I know.

  27. Just for clarification (in response to some Twitter critter), I worked for Orchestra Hall and was paid by the Orchestral Association, which also paid the members of CSO. When CSO went to Ravina (since 1936), Orchestra Hall featured concerts (Gordon Lightfoot, Cleo Laine, Danny Kaye& Jack Benny, the Clancy Brothers & Tommy Makem and the great Red Army Choir) put on by impresario Harry Seltzer, a lovely old gent.

    Also, Michael Butler put on a Summer of Love featuring the Guru Maharashi, the art of Peter Max and sounds of the Young Rascals! They were great guys.
    Gotta pay the bills.

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