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Rate the new Preckwinkle video

Tuesday, Dec 16, 2025 - Posted by Rich Miller

* From Cook County Board President Toni Preckwinkle’s website, StopTrumpsGuy.com

Script

It’s politics at its worst. Rich guy needs something done, so he gets a guy on the inside to help.

And Donald Trump’s man in Chicago is Alderman Brendan Reilly.

Reilly took thousands in campaign cash from Trump and used his position to benefit the Trump Organization. Reilly even personally signed the paperwork to let Trump to face our skyline.

With Trump now trying to rule Chicago, it’s the wrong time for his guy, Reilly, to run Cook County.

Discuss.

       

65 Comments
  1. - Tom - Tuesday, Dec 16, 25 @ 9:15 am:

    That is going to leave a mark on Brendan. It’s an A plus. He needs to respond quickly.


  2. - Three Dimensional Checkers - Tuesday, Dec 16, 25 @ 9:16 am:

    Too ironic for me consider Preckwinkle probably lost the 2019 Mayor’s race because of her connection to Ed Burke.


  3. - Teve Demotte - Tuesday, Dec 16, 25 @ 9:17 am:

    Effective ad. The progressive base of the party is already mobilized and loaded for bear. There’s an old adage in politics: “When you are explaining, you are losing.” Riley will have a very tough time against Toni.


  4. - Jr. Neef - Tuesday, Dec 16, 25 @ 9:21 am:

    wow, That is a good solid hit. If your responding you’re losing but with this he needs to respond or he will be losing.


  5. - Billionaire Budster - Tuesday, Dec 16, 25 @ 9:23 am:

    A plus. Can anyone say bye bye Brandon?


  6. - Lakeview Larry - Tuesday, Dec 16, 25 @ 9:26 am:

    A+. 10/10.


  7. - Pundent - Tuesday, Dec 16, 25 @ 9:36 am:

    Devastatingly effective. It’s the equivalent of Mike Tyson destroying his opponent in 30 seconds.


  8. - Homebody - Tuesday, Dec 16, 25 @ 9:51 am:

    This just reminds me how much I hate the Chicago alderman fiefdoms and how much power they have. It is a system basically designed to maximize low level corruption as a necessary evil.


  9. - 47th Ward - Tuesday, Dec 16, 25 @ 9:58 am:

    They are “Vallasing” Reilly. I get it, and it’s a smart move. Except the last time they did it, we got stuck with Brandon Johnson. How many Chicago voters would like a do-over on that one?

    Toni Preckwinkle has had a good run. Sadly, she ran so far left that it makes me look like a Republican. And I assure you, I am no Republican. Neither is Reilly.


  10. - Rich Miller - Tuesday, Dec 16, 25 @ 10:00 am:

    ===They are “Vallasing” Reilly===

    This goes well beyond that.


  11. - low level - Tuesday, Dec 16, 25 @ 10:00 am:

    Daaaaaaamnn. Brutal. Right down to spelling his name wrong in a dissing kind of way. I am curious to see how Brendan’s people will respond. He has very good people around him so it should be good.


  12. - Peoples Republic of Oak Park - Tuesday, Dec 16, 25 @ 10:15 am:

    I mean, yes good hit. I think though Toni has a story to tell and should have led with that.


  13. - Rich Miller - Tuesday, Dec 16, 25 @ 10:16 am:

    ===should have led with that===

    Looks to me like the real object here is to dry up his money before this gets outta hand. Telling her story would not have done that.


  14. - Demoralized - Tuesday, Dec 16, 25 @ 10:20 am:

    The picture of him smiling and shaking hands with Trump is enough. Being linked to Trump is a death knell in Illinois and especially in Chicago.


  15. - TNR - Tuesday, Dec 16, 25 @ 10:20 am:

    == He needs to respond quickly. ==

    Noticed on WGN news this morning that instead of his Preckwinkle hit piece he’s running a new ad touting his support for abortion rights…so looks like he’s responded by looking to boost his progressive credentials.


  16. - Streator Curmudgeon - Tuesday, Dec 16, 25 @ 10:22 am:

    That’s a powerful ad. Trump is a villain in Chicago and tying Reilly closely to him puts the stink on Reilly too.

    This does exactly what Preckwinkle wanted it to do.


  17. - Frida's Boss - Tuesday, Dec 16, 25 @ 10:25 am:

    It’s a big hit. In Cook County, Trump is Public Enemy #1.
    There is no response possible.
    Deflecting may be the only response possible.
    Toni’s record- increased taxes, job losses, property taxes, tie her to everything negative in Cook County.
    The question is, do people care more about her record than Trump?
    I wouldn’t bet on it


  18. - 47th Ward - Tuesday, Dec 16, 25 @ 10:25 am:

    ===…the real object here is to dry up his money…===

    Probably right about that, but how many visitors to Preckwinkle’s web site are thinking of donating to Reilly. If she puts this on the air, it’s going to make a big dent in his FR and support. If it’s only on the website, meh.

    We’ll see how it plays out.


  19. - Rich Miller - Tuesday, Dec 16, 25 @ 10:30 am:

    ===but how many visitors to Preckwinkle’s web site===

    She’s only targeting a relative handful of people.


  20. - Just Me 2 - Tuesday, Dec 16, 25 @ 10:30 am:

    The cool thing about being the downtown Alderman is that every bar, every restaurant, every hotel, and every building needs the Alderman’s signature for their sign, valet, and operating permit.

    The thing that sucks about being the downtown Alderman is that every bar, every restaurant, every hotel, and every building needs the Alderman’s signature for their sign, valet, and operating permit.


  21. - lake county democrat - Tuesday, Dec 16, 25 @ 10:31 am:

    Effective. I’d counter with her support/endorsement of Barrios and Madigan-word and tie it to property taxes. The whole donation-wink/nod-property tax appear scheme may have been legal, but people hate it.


  22. - Mason County - Tuesday, Dec 16, 25 @ 10:31 am:

    Has that usual little sing-song voice with its attempts to belittle the opposition. Both sides annoyingly use it.

    Effective. Yes. It strikes a core theme with the liberal base.


  23. - Rich Miller - Tuesday, Dec 16, 25 @ 10:31 am:

    ===her support/endorsement of Barrios and Madigan===

    Um, Brendan worked for MJM.


  24. - TNR - Tuesday, Dec 16, 25 @ 10:38 am:

    == If she puts this on the air ==

    I saw it yesterday on WGN. BTW, you gotta watch Channel 9 news in the morning during political season…home of the political ad.


  25. - Three Dimensional Checkers - Tuesday, Dec 16, 25 @ 10:38 am:

    ===Looks to me like the real object here is to dry up his money before this gets outta hand.===

    It might be too late for that.


  26. - low level - Tuesday, Dec 16, 25 @ 10:41 am:

    Just Me 2 knows what he is talking about. Brilliant comment. I’ve often thought about that dichotomy myself.


  27. - Amalia - Tuesday, Dec 16, 25 @ 10:41 am:

    A+ Now Reilly should answer with Kim Foxx. Foxx did not have an active law license when she declared for State’s Attorney. She was criminal justice adviser to Toni. Every bad crime makes people remember what a disaster Toni was. All politics is local. you can’t get more local than the attacks on women in Chicago.


  28. - lake county democrat - Tuesday, Dec 16, 25 @ 10:42 am:

    I realize that, but it won’t be the first time somebody successfully deployed hypocrisy in a campaign ad. Bill Clinton ran ads in the south in 1996 promoting him as an opponent of gay rights.


  29. - popcorn - Tuesday, Dec 16, 25 @ 10:44 am:

    Surely the Reily cmapign knew a hit like this was coming. Those video clips are around 15 years old? I just want to see how they respond.


  30. - Biden voter here - Tuesday, Dec 16, 25 @ 10:47 am:

    You’re right, the Joe Biden delegate is a Trump supporter…

    Come on people


  31. - Garfield Ridge Guy - Tuesday, Dec 16, 25 @ 10:51 am:

    If an effective ad is “just saying an untrue thing,” then A+ ad.


  32. - low level - Tuesday, Dec 16, 25 @ 10:57 am:

    == If an effective ad is “just saying an untrue thing,” then A+ ad.==

    Can you specify what part is untrue?


  33. - SwSider - Tuesday, Dec 16, 25 @ 11:01 am:

    ==they are Vallasing Reilly==

    It’s actually his past actions that are making him look like a Republican.

    Also, the number of people who don’t realize how close Chicago came to a disaster with Vallas in Chicago and Trump in Washington is worrisome.


  34. - benniefly2 - Tuesday, Dec 16, 25 @ 11:07 am:

    Saw it on tv yesterday and thought it was likely the only ad she needs to put out this year. Just absolutely brutal.


  35. - Steve - Tuesday, Dec 16, 25 @ 11:07 am:

    I really thought Trump’s guy on City Council was Alderman Ed Burke when he was there. Go figure.


  36. - levivoted4judy - Tuesday, Dec 16, 25 @ 11:10 am:

    OW, this is a great ad. She did something similar to Richard Boykin with some flyers calling him a closet Republican because he got an endorsement from the U.S. Chamber of Commerce. I thought it was ridiculous because he was Danny Davis’ former chief of staff, but a lot of people bellieved it. I know the root of the Reilly/Trump relationship (he went to school with one of his kids), but Trump is so hated in a lot oc Chicago, this is a devastating punch. BR needs to get out in front on this ASAP.


  37. - charles in charge - Tuesday, Dec 16, 25 @ 11:11 am:

    ==They are “Vallasing” Reilly.==

    Yes, because he’s of the same ilk as Vallas. The reason this is an effective line of attack is because it’s a legitimate critique of these guys based on their actual history and policy positions.


  38. - ZC - Tuesday, Dec 16, 25 @ 11:15 am:

    Reilly is absolutely a Democrat, full stop. It’s a problem for the Democratic party (especially in Chicago) if they push out all the Reillys from the coalition.

    It’s also perfectly true that, all the way back to his unseating Burton Natarus, he’s built a not-insubstantial chunk of his support on disaffected Chicago Republicans who are looking for the least worst Democrat in their eyes they can support. And I’m sure that was part of the calculus in 2026, to get every Republican and conservative independent in Cook (and there are plenty) to back him over Toni.

    So that was always gonna be a delicate dance, appealing to disaffected Republicans (for your whole career) while still proclaiming yourself a Democrat, while Donald Trump is setting the Republican brand on fire with a blowtorch in Cook County. Even in Chicago’s tony wards like the 42nd and 2nd there’s a lot of Yay-Vallas-Boo-Trump voters. So I’m unsure even a politician with Reilly’s smarts can thread this needle.


  39. - Rich Miller - Tuesday, Dec 16, 25 @ 11:20 am:

    ===to get every Republican and conservative independent in Cook (and there are plenty) to back him over Toni.===

    That’s not his plan. This is a Democratic primary. It’s not the mayor’s race.

    You’re right that he’s a smart guy and I’m sure he anticipated this, however.

    But this is a Democratic primary. Keep that in mind.


  40. - Peoples Republic of Oak Park - Tuesday, Dec 16, 25 @ 11:24 am:

    I get trying to dry up his money is a strategy, but I think that Brendan’s donors don’t care. Pretty much any moderate is going to be painted this way. See the whole city budget fight. Granted they don’t have videos of them shaking hands with him.


  41. - Iron Duke - Tuesday, Dec 16, 25 @ 11:30 am:

    Preckwinkle’s States Attorney lost

    Her hand picked Mayor is floundering

    Voters are hopping mad about property taxes

    She is in for a battle and one negative ad is not going to eliminate a challenger who is qualified in a tough year for any incumbent


  42. - Jocko - Tuesday, Dec 16, 25 @ 11:33 am:

    ==Reilly personally signed the paperwork to let Trump deface our skyline.==

    Oof (exclamation point). That (and Trump’s money) is gonna leave a mark.


  43. - Chicago Voter - Tuesday, Dec 16, 25 @ 11:42 am:

    =If she puts it on the air= I’ve seen this ad a number of times. The first time I saw it I said out loud to myself wow, that’s going to hurt.


  44. - Excitable Boy - Tuesday, Dec 16, 25 @ 11:44 am:

    - How many Chicago voters would like a do-over on that one? -

    I’d still take Johnson over Vallas.

    That is a perfect ad. A+


  45. - Three Dimensional Checkers - Tuesday, Dec 16, 25 @ 11:47 am:

    If I was Reilly, I would respond with a good endorsement. Tying Preckwinkle to Brandon Johnson would be good too, but Kim Foxx and the parade of grievances are going to hurt his chances.


  46. - Mazol Tav - Tuesday, Dec 16, 25 @ 11:50 am:

    Reilly is done. Mazol Tov, Toni.


  47. - Rudy’s teeth - Tuesday, Dec 16, 25 @ 11:51 am:

    That ad has quite a bite. Surely, Brendan Reilly’s team will remind voters of godmother Toni Preckwinkle’s support of former Cook County State’s Attorney Kim Foxx and more recently Brandon Johnson Mayor of Chicago.
    From the tone of the ad, Miss Toni is not ready to retire from public office.


  48. - HappyGoLucky - Tuesday, Dec 16, 25 @ 12:09 pm:

    Lot of armchair commenters today.

    I can see very few if any have ever worked on a campaign.

    You go on the attack when the polling shows you losing.

    And to do it this early?

    Preckwinkle must be afraid.


  49. - Just Me 2 - Tuesday, Dec 16, 25 @ 12:13 pm:

    Didn’t Reilly hire a Trump person to be his COS at one point in time? Someone with more time on their hands can dig that up.


  50. - Thomas Paine - Tuesday, Dec 16, 25 @ 12:15 pm:

    What makes the ad effective is the video of Trump and Reilly together. Put Reilly’s ad attacking Preckwinkle on affordability next to this ad, and tell me who is gonna win. Preckwinkle might not need another ad.

    === Preckwinkle’s support of former Cook County State’s Attorney Kim Foxx and more recently Brandon Johnson Mayor ===

    It’s a Democratic primary, that will not work. Also, it comes across as “I just don’t like Black people.”

    Also, it just reinforces the “Guilt by Association” framework. Reilly is not going to win an argument over “Who has the worst friends.”

    === Reilly is absolutely a Democrat, full stop. ===

    So is Robert F Kennedy, Jr.

    You can be a Trump Democrat.

    === Yes, because he’s of the same ilk as Vallas. ===

    I’m not sure “ilk” is the right word. Reilly was spokesperson for Vallas when he first ran for office and remains a close political advisor and supporter. Reilly and Vallas are allies.

    I imagine the only reason Reilly is not running for Mayor is because he is supporting Vallas once again, or if Vallas drops out then Alexi.


  51. - Rich Miller - Tuesday, Dec 16, 25 @ 12:16 pm:

    ===Preckwinkle must be afraid. ===

    That’s just the sort of standard armchair observation that you derided.


  52. - Tom - Tuesday, Dec 16, 25 @ 12:18 pm:

    ~She is in for a battle and one negative ad is not going to eliminate a challenger who is qualified in a tough year for any incumbent~

    Trust me, if I were running Toni’s campaign, I would cut this ad four different ways, all with the basic message. You don’t buy a website and do all that if it’s a one-trick pony. The ad is good–real good and the hit is legit. Answering it with “I’m pro-choice” ad isn’t going to stem the bleeding. To be honest, I’m not sure he can.


  53. - ArchPundit - Tuesday, Dec 16, 25 @ 12:20 pm:

    ===You go on the attack when the polling shows you losing

    Or to define your opponent. If you have the resources as an incumbent, there aren’t many cases where you wouldn’t want to define your opponent before they can define themselves.


  54. - Walker - Tuesday, Dec 16, 25 @ 12:21 pm:

    Ad is a good early strike, for funding purposes.

    But I didn’t think Reilly, or any other Alder, had a decent chance against Toni anyway. This race is hers to lose


  55. - Thomas Paine - Tuesday, Dec 16, 25 @ 12:27 pm:

    === You go on the attack when the polling shows you losing.

    And to do it this early?

    Preckwinkle must be afraid. ===

    Is the 42nd Ward out in force today?

    To recap:

    1. Reilly launched the first ad.
    2. Reilly’s first ad was negative.
    3. This is not the ad of someone who is “afraid.” This is an ad from someone who is confident they know exactly how to take Reilly down.

    I have seen ads from people who are losing, and “afraid.” They are Kitchen Sink ads that throw every negative out there because they have not polled any of them, they are not sure what will be effective or stick.

    This ad looks to me like a message that was poll-tested, it uses very simple language that could easily be in a poll question:

    “Reilly took thousands in campaign cash from Trump and used his position to benefit the Trump Organization. Reilly even personally signed the paperwork to let Trump deface our skyline.”

    Simple, provable, testable. I bet 80% of Democratic voters said it would make them less likely to vote for Reilly.


  56. - Three Dimensional Checkers - Tuesday, Dec 16, 25 @ 12:28 pm:

    ===I imagine the only reason Reilly is not running for Mayor is because he is supporting Vallas once again, or if Vallas drops out then Alexi.===

    If Paul Vallas wanted to run for Mayor, why would he take a job with IPI? Does anyone really think he lost because he was not conservative enough? Sorry if this is off topic, but there are not good facts for this theory, and it literally feeds the Mayor’s dysfunction.


  57. - Sue - Tuesday, Dec 16, 25 @ 12:38 pm:

    One day Trump will be gone and Illinois Democrats will lose their excuses and have to explain their own governance failures- Trump has as much to do with our fiscal messes as the man on the moon but why let facts get in the way of fiction


  58. - Pundent - Tuesday, Dec 16, 25 @ 12:58 pm:

    =You go on the attack when the polling shows you losing.=

    Perhaps. It’s way to early to put odds on winners and losers. But as Paul Vallas knows, once you’ve been defined as a Republican running as a Democrat you just can’t recover. Reilly’s will now spend the rest of the campaign dealing with that label.


  59. - Thomas Paine - Tuesday, Dec 16, 25 @ 1:22 pm:

    === If Paul Vallas wanted to run for Mayor, why would he take a job with IPI? ===

    For the legitimate income and the continued exposure to GOP money it brings.

    Vallas is the top polling candidate.

    He has not raised money lately, but he also has not closed his campaign account.

    He has $23K in campaign debt, and unless I missed it he has not said he is not running.


  60. - Three Dimensional Checkers - Tuesday, Dec 16, 25 @ 1:35 pm:

    ===the continued exposure to GOP money it brings.===

    Which he was not exactly the best steward of last time. I know Illinois Republicans are quixotic by nature, but come on.


  61. - Sue - Tuesday, Dec 16, 25 @ 1:52 pm:

    My guess is there 10’s of thousands of Chicago voters who today wish Paul Vallas was the Mayor of Chicago instead of Brandon Gates Johnson


  62. - Rich Miller - Tuesday, Dec 16, 25 @ 2:08 pm:

    ===My guess is===

    And your point?

    Do you know why this is such an effective spot? Hit dogs gonna holler, and some of y’all are howling at the moon right now.

    Again, I’m figuring Brendan anticipated this. But this is a big hit.


  63. - low level - Tuesday, Dec 16, 25 @ 2:10 pm:

    ==I can see very few if any have ever worked on a campaign==

    That is a really dumb comment to make on this page especially. There are true experts with years of experience here. I learn all the time.

    ==One day Trump will be gone and Illinois Democrats will lose their excuses ==

    lol. Whatever.


  64. - Amalia - Tuesday, Dec 16, 25 @ 2:53 pm:

    and now Toni’s Mayor is straight up criticizing that the alternative budget includes more debt collection. hilarious that he thinks people should not pay what they owe. Toni gave Chicago a fiscally clueless Mayor.


  65. - Kayo Punch - Tuesday, Dec 16, 25 @ 4:59 pm:

    It is a damaging hit piece attacking Reilly and linking him to Trump. It rates a solid “A.” But by the same token it does not say a single word about Preckwinkle’s accomplishments.

    Reilly’s best response would be to highlight the massive property taxes in Cook County and to link Preckwinkle to Brandon Johnson and Kim Foxx.


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