28 Ideas for a Week in Chicago

I am Isaac Saul, the conflicted executive editor, where I write an independent, nonpartisan, subscriber-supported political newsletter that summarizes the best arguments across the political spectrum in the day's news, followed by "my take." Transparency is key for such work,please subscribe to Tangle here !

I spent this week at the Democratic National Convention.

This is my first convention. I have been reporting on politics for a decade and have personally covered many major political events, but the party convention is truly unlike anything I have ever experienced before. Aside from walking through the halls of Congress, you won’t find these high-profile politicians anywhere else. In fact, the star power at the convention is larger than the scale of Congress: governors mingling with mayors, mayors, heads of famous organizations, celebrities, and influencers all in attendance. One moment I was listening to Bill Clinton speak, the next John Legend was performing, and Oprah Winfrey was addressing the audience.

I have been jotting down everything I noticed, big and small. Today, as the convention wraps up, I am clearing out my notebook.

Twenty-Eight Thoughts on the Convention

1. The experience of the entire convention is vastly different from what you see on social media or television. On one hand, I would see people saying the arena was empty when it was packed, or that there was significant disruption, which I didn’t even notice. Experiencing it this way is a reasonable way to get lost in translation. Similarly, pro-Palestinian protests were all oversocialmedia, but it was easy to miss them in person. The whole week I was in Chicago, I saw a group of protesters—about 20 people holding signs, calling for a ceasefire and reading the names of the dead. That was it. All the images of chaos and fighting with police didn’t actually interrupt the convention in any meaningful way. Moreover, the schedule of the convention was highly choreographed, with instructions for cheerleading fans at certain times and signs distributed wherever you looked. But on television, it looked much more spontaneous.
2. Democrats deliberately leaned into patriotism and revived the word "freedom." Eight years ago, if I told you about a rally where "USA!" chants erupted every few minutes, with "freedom" as a theme, you would think I was talking about a Trump rally. However, nearly every speaker leaned into themes of patriotism and freedom throughout the week. Since taking over the ticket, the Harris campaign has made a noticeable pivot. I am not the only one who noticed this.
3. The most striking speech of the week was Michelle Obama’s on Tuesday night. Frankly, it was one of the most effective political speeches I have ever heard. It was so effective that she was praised by conservative pundits all week, some of whom warned their colleagues not to underestimate its power. It’s hard to pinpoint exactly why it was so effective or how she managed to win praise from across the aisle, but she did. There was no policy—just the line she drew between what she believes Democrats represent and everything she believes Trump represents. Every other speech (including her husband’s immediate appearance) just felt like it had almost none of the same juice.
4. Speaking of the lack of policy: the programming consistently avoided policy and instead focused on defining Harris and Walz as people, rather than as executives. The DNC literally had a childhood friend of Harris speak, then a former neighbor of Walz from Minnesota. These people spoke after former presidents and current senators—sharing little anecdotes about how they helped each other or (rather dull) family stories.
5. Another thing I haven’t heard is that Harris might be the first woman president. I am fascinated by the decision to downplay this angle. In 2016, many speeches focused on Hillary Clinton breaking the glass ceiling. For Kamala, I can’t think of a speech that made her candidacy’s historic nature (ironically) more prominent. Compared to Harris becoming the first female president, there were more mentions of Trump’s infidelity to his wife.
6. Monday’s swan song for Biden felt sharp. Attendees were in tears, hands over their mouths, many shouting how much they loved him (I joked to Jon that dropping out was the most popular thing he ever did). Biden and his family looked at me like someone who just survived a disaster, trying to find their way.
7. A little drama played out here between content creators and traditional journalists. The DNC rolled out a blue carpet for content creators and influencers, who got private lounges, free food and drinks, and access to big-name politicians. Meanwhile, journalists were crammed into nosebleed seats, fighting for credentials, competing with politicians for poor internet and bad opportunities. Strategically, I think this is smart: the DNC knows it will get friendlier coverage by relying on content creators and attract younger voters. Morally, I hate it—traditional journalists having access to real interviews (rather than PR hit pieces) would promote greater transparency and balanced reporting. Personally, I straddle the line between being a journalist and an online content creator, so I try to enjoy the best of both worlds.
8. I said something about this in a tweet on Monday. Apparently, it did make some content creators angry, who started making videos and angrily posting about my tweet. Ironically, they all seemed to think I was a mainstream media journalist, frustrated that they were getting access, when in reality I was just reporting on some very obvious things to those attending the convention (and I was getting similar access; it’s telling that I told DNC organizers I have a YouTube channel). But now that I have their attention, let me say this: the DNC invites you backstage and ensures you can interview people with a reason that is not because you are the truth-teller who reports the news better than everyone else. They know you are a fan, and they will provide you with worshipful coverage and help advance their agenda.
9. Many conservatives attended! Charlie Kirk, Matt Walsh (who disguised himself), Kellyanne Conway, Rudy Giuliani, and Mike Lindell (who was a stand-in) all attended the convention. On cable news, Fox News has been the largest media setup and presence by far.
10. I was about 20 feet from Pennsylvania Governor Josh Shapiro’s speech, and it was incredible. I think over time, his shtick will wear thin. Aesthetically, Tim Walz exudes authenticity and kindness, while Shapiro feels scripted, a bit polished. The criticism of Shapiro’s “Obama-like” approach resonated with me, and after seeing how both played to a larger audience differently, I think I understand why Harris chose Walz over Shapiro. I think she is smart. Again: I am only talking about political performance here, not policy or legislative ability, but when you are not the incumbent, performance skills are a crucial component of winning elections.
11. Speaking of performance skills: I saw Shapiro, Senator Mark Kelly (AZ), and Governor Roy Cooper (NC) speak this week in prime time. I also saw Transportation Secretary Pete Buttigieg, Governor JB Pritzker (IL), and Governor Andy Beshear (KY). Based on their speeches, how they interacted with the audience, the reception they received, and how they conveyed their messages, I think Harris clearly made the right choice with Walz.
12. Whatever its worth: so far, the most effective part of Walz’s stump speech was when he discussed his issues with infertility and the miracle of children. When the current viral moment with his son happened, people in the audience cried, and this part of the speech—emphasizing the freedom to keep government out of personal family decisions and claiming Republicans could threaten treatments like IVF—landed in the room.
13. JD Vance made a joke about Walz going to Chicago so he could finally serve in a “war zone.” I have to say, despite the issues, Chicago is a lovely city. I have been here a few times before, but I forgot how much I love it. Delicious food. Kind people. Beautiful waterfront and parks. Given how much news I consume, these are not the things I think of when I think of Chicago, but this week, it was a good reminder of how distorted people can be about more sensational news coverage.
14. Walz and Democrats have been attacking JD Vance for going to Yale. Walz said, “Now, I grew up in Butte, Nebraska, a town of 400 people.” “My high school class had 24 kids, and none of them went to Yale.” I really don’t like this line of attack at all. Is Vance’s viewpoint less valid, or is his rural “credentials” less valid because he is a smart person who escaped poverty and went to an Ivy League school? This strikes me as a very stupid, ugly, and self-deceiving line of attack. I don’t know who came up with it. Vance’s story is a powerful and remarkable story worth celebrating.
15. The difference between the headliners and the big names in prime time is stark. This is another reminder of how much politics is about performance, and how important public speaking is for advancement. Most viewers will only see the prime-time speeches, but every night there are 3-4 hours of speeches from Democrats of various stripes and stations, many of which are snoozers.
16. Keep an eye on Maryland Governor Wes Moore. After seeing him at the convention center, watching his speech live, and listening carefully to how people talked about him, it seems this guy is eyeing the White House. I think he will run for president in the next four to twelve years.
17. I spoke with North Carolina Congressman Wiley Nickel, who focused on the idea that Democrats should go all out to win North Carolina, which would open up the electoral college map for them. It seems the party is listening. Harris has visited the state 16 times during her vice presidency, and her tar heel polling numbers look better. This is an interesting strategy: essentially, North Carolina is Harris’s insurance policy if she doesn’t take the entire blue wall of Pennsylvania, Michigan, and Wisconsin. If she flips North Carolina and holds Pennsylvania, she only needs to win one of Wisconsin, Michigan, Georgia, or Arizona to win the race. And if she secures North Carolina and Nevada, that gives Harris a path to victory without Pennsylvania.
18. President Obama had some very tangled messaging about crossing the aisle and giving grace to your political opponents. He suggested treating those we disagree with like family members we love who say things that make us cringe. I appreciated this message, as well as his commitment to how we can better cross the aisle in five to six minutes. Unfortunately, in the same speech, he made a very subtle joke about Trump’s insecurity regarding the size of his penis, which now overshadows all his other statements.
19. Democrats tend to lean into a law-and-order atmosphere from the Clinton era. They constantly tout Harris’s record as a prosecutor, and on the last night, ran out unified officials who gave 180 speeches on their party platform to increase funding for police. Harris’s introduction video even had a moment from years ago when they were among them.
20. Harris’s speech was a bit like a Rorschach test. I follow a set of thinkers on X, and it was fascinating to read their responses in real time. The liberals I follow were over the moon, thinking she hit a home run and delivered a powerful, grounded speech that defined herself as a happy warrior to the public. The moderates I follow said it was a solid speech that did exactly that—Harris’s victory. The conservatives I follow said she looked nervous, sounded disconnected, and the whole thing would remind voters how unlikely she is. As someone who watched almost every address this week, I think Harris was in the top eight in terms of effectiveness and delivery. I think she did well. In the words of conservative radio host Erick Erickson, “It’s easy to dig, but her speech was more disciplined than [Trump’s] training. She seized the opportunities he missed.”
21. These speeches are always hard to judge objectively, but one way to assess them more objectively is to look at focus groups and fundraising. In Allentown, Pennsylvania, a CNN focus group of eight undecided voters watched Harris’s speech and then rated it. Three gave her an A, three gave her an A-, one gave her a B, and one gave her an A. Of the eight voters, seven were decided: they said they would vote for Harris. Within hours after the speech, Democrats also raised millions of dollars. So if you don’t believe I’m a good speech, that’s some indicators.
22. Something notable happened in the DNC last night: Donald Trump posted about Republican Georgia Governor Brian Kemp, who has been attacking him (along with his wife) for the past few weeks: “Thank you @briankempga for all your help and support in Georgia, where the victory is crucial to the success of our party and, most importantly, our country. I look forward to working with you, your team, and all my friends in Georgia to make America great again!” It’s hard to overstate how rare this kind of reversal is from Trump, which makes me think his internal polling in Georgia must be shocking.
23. When you attend an event like this, it’s easy to drink the Kool-Aid. It’s like watching a game in a sports bar, with fans devoted to one team. Still, the energy is palpable, and being surrounded by all these Democratic activists, experts, and politicians makes me wonder what the ceiling is this year. I thought of a thought: what if this is the first strong, vibrant, powerful ticket of Democrats running since 2012? What if Hillary Clinton and Joe Biden actually had pretty bad campaigns or mediocre runs, but because of Trump’s unpopularity with moderates, it was a tight race? What if, aside from good polling, grassroots energy, and fundraising, there are hidden Harris voters? If so—if the Harris-Walz ticket can maintain Obama-like momentum—could they win in a landslide? Maybe this race won’t be so close after all?
24. Conversely, it’s very possible that with an untested, unproven candidate, we might see a friendly media cycle that is destined to return to earth in the coming weeks. In that case, we are looking at another election that will be decided by tens of thousands of swing states, many of which are states where Harris ultimately becomes a loser before election day.
25. I think Democrats should let Palestinian voices on stage this week. There are plenty of pro-Israel voices, and the moment with the parents of American hostages in Gaza was very powerful. But a pro-Democratic Palestinian voice would also be strong. No speaker at the convention clarified the remarks, so why wouldn’t Democrats also show they are a big tent party by giving those voices a few minutes? The RNC made space for union bosses and amber roses—that’s what activating a big tent looks like. The omission doesn’t make sense to me. Moreover, with the strong uncommitted movement growing, I think this is a political dereliction of duty.
26. No Palestinian or person from the uncommitted movement made the best argument that this is a coronation event for the nominee. By definition, you will undoubtedly disqualify yourself from taking the stage in the room. However, I still think this could be a moment of unity, and something to activate progressives and Muslim voters—yielding a small piece of ground.
27. Harris threaded the needle on the issue of Israel and Gaza. Her remarks clearly indicated she would continue to serve as a staunch ally of Israel, which aligns with most of the party. But she also talked about the terror inflicted on Palestinians, which many other candidates did not.
28. The end of the DNC may mark the end of the honeymoon phase for Harris and Walz. At some point next week, the media’s vice grip will end—new stories will be written, criticism will continue, and Harris will have to face interviews, and scrutiny will be dialed up to 10. As we sit here today, I think Harris and Walz successfully captured this momentum in this election, and now they are in the driver’s seat. You don’t have to take my word for it—just look at the polls, the betting markets, and fundraising struggles. But there is a long way to go, and Harris and Walz still have to navigate through.

A Few Other Odds and Ends

• I saw New York Times columnist Ezra Klein riding a fancy scooter, which felt very on-brand.
• Senators have a glow. I can’t quite explain it. When you see them, even if you don’t know them, you just know. They shine in a special way.
• The biggest barrier to getting interviews is that people don’t know who we are and whether they can trust us.
• Some pro-Palestinian protesters read the names of the dead in Gaza through a megaphone, and several DNC attendees created some very bad optics by plugging their ears. I walked past the protests too. As bad as those videos look, the sound was incredible.
• Many people at the convention seemed to hate traditional media as much as conservatives do.
• Jon ran into Jon Favreau while going through a Secret Service checkpoint and agreed to a pen swap, kicking off a more advanced security check.
• Logistical issues were bad on day one, bad on day two, but resolved before day three.
• Every few speakers, the organizers would sprint through the convention center, distributing thousands of new signs like “America” signs or “Walz for Coach” signs or other signs. These signs were dependent on the speakers, and they were an interesting way to understand the optics the event organizers wanted to present.
• There were 15,000 media members in attendance. Fifteen thousand.
• On the first day of the convention, as we approached the center, an older Black man at the corner of the United Center was screaming at attendees that he was voting for Donald Trump, while the whole community was broadly represented by Harris and the Democrats. It was a very interesting moment.
• The extremely expensive suites throughout the convention center were filled with big donors and power players who couldn’t get in. CNN’s Chris Cuomo called out this dynamic in a viral clip from the convention floor.
• I have to give a shout-out to Saager Enjeti, who runs the podcast Breaking Points, which is one of my favorites. He is a classic example of a very kind, friendly person, and also a discerning analyst.
• When Harris appeared on night one, it was the second loudest roar I’ve heard the arena get. #1 was when I broke the NBA scoring record at Madison Square Garden while sitting in the stands.
• I most likely see the 2028 presidential list as: Wes Moore, Josh Shapiro, Pete Buttigieg, and Gretchen Whitmer (in that order).
• I’m a bit surprised Bill Clinton is still invited to these things. He’s not only reliably accused of sexual assault, but he’s also a wildcard—he was the only speaker I saw who stepped away from the podium for a few minutes during his speech.
• I interviewed a congressman who accidentally walked away while I was giving him my lav mic. When I dragged him back to retrieve it, he told me a great story about Al Gore once accidentally wearing a microphone in the bathroom, and everyone heard his business. Since then, he’s been worried about walking away with a mic on, and this was his first time really doing it.
• When Tim Walz said, “Never underestimate public school teachers,” he got one of the biggest roars from the crowd I heard all week.
• I don’t know who started the rumor that Beyoncé was attending, but I had so many people tell me at the DNC that it was true, even TMZ reported it (though their reputation is hit or miss, they rarely get these things wrong). I’m not sure what soured, but it seemed like she would be there.
• Ro Khanna (D-CA) is much taller than I can find any reliable sources on (some list him at 6'2”, but we walked past him, and he was much taller than I imagined. Very tall.

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