Friday Mailbag: Summit Edition!
All eyes on Alaska
📅 PROGRAMMING NOTE: I am doing a livestream over at my YouTube channel at 1 pm eastern today. Come! Hang out! Ask questions! Click here to join!
Alaska is the center of the political universe today with Donald Trump and Vladimir Putin sitting down there to talk about the possibility of ending the war between Russia and the Ukraine.
Does the self-professed greatest deal-maker in the world find a way to a lasting peace with a man who has vexed American presidents for more than two decades?
In the meantime, I answered a whole lot of your questions about the week that was in American politics.
Everyone can read my first few answers in the Friday Mailbag. But only PAID subscribers get access to the full Mailbag every week. What else do you get as a paid subscriber? Glad you asked!
Exclusive access to my weekly Monday podcast with Chuck Todd.
An exclusive Sunday email with a list of recommendations from yours truly — a podcast, an article, a YouTube video, a Substack, a song, a book, a TV show — that I think you will dig.
Exclusive access to my rankings of the 2026 Senate playing field and the 2028 presidential race
All that for $6 a month or $60 a year! Do it!
Let’s open the mail.
Q: Can anyone from the media rationalize why Trump is the sole negotiator w/ Putin on behalf of Ukraine? It’s hard to imagine Trump not caving or kowtowing to Putins insistence on taking over part or all of Ukraine?? So Trump’s got the authority to negotiate on behalf of Zelensky? And Why isn’t Zelensky there? Cause Putin doesn’t want him there? WTF? And why aren’t any European leaders there, since they’re more vested proximity wise than the Ole US of A? Crazy times!
A: A few thoughts.
I DO think — obviously — it would be better if Zelensky was in this meeting with Trump and Putin. My guess is that Putin made Zelensky not being there his sine qua non for having the meeting in the first place. Trump could have refused — and I am sure his critics would have wanted him to — but I get the logic that sitting down with Putin is better than not sitting down with him.
As for why it’s Trump and not European leaders, that one seems easy to me: The U.S. is the world power (along with China). Our ability to cripple Russia with economic sanctions is unlike any other nation in the world. And our military might commands respect from someone who thinks like Putin.
Again, I think you have to be very careful not to assume that all of this is bad for the U.S. or the world. I think the meeting is VERY high stakes. But I DO think it is a good thing that the U.S. president is sitting down with the Russian president to try to end a brutal and bloody war.
Could it go wrong? Sure. Trump could get suckered into a bad deal that he can’t sell to Ukraine or the rest of the world. He could walk out in a huff — and set back future negotiations. There’s a lot of ways it could go. But, again, Trump and Putin talking is a necessary precursor to the end of this war. And today they will talk.
Q: What is the chance that Trump just fawns over Putin, like in the past, and sells out Ukraine?
A: I think that’s unlikely. Trump is a highly aware that the narrative going into this summit is that Putin is a master manipulator — and has worked his, uh, magic on past presidents.
Trump hates looking like a fool or a rube — he fashions himself as the street-wise guy who sees all the angles. So I think he will be more on guard with Putin than he was back in 2018 in Helsinki.
That said, both of these guys are HUGELY unpredictable — and revel in that. So who knows!?
Q: I think this is a really important question I hope you’ll answer. You say you’re always asked if you think democracy is in trouble. And your response has always been that it’s not. Why? Because it’s not. Can you please elaborate on why you feel that way, beyond just saying you don’t think it’s at risk? What are you seeing that the rest of us are missing? Don’t just tell us that no one knows what the future will bring. Don’t just accuse people of claiming the sky is falling. Give us a deeper answer and perhaps even explain a scenario or action which would cause you to feel differently. I believe many of us are very concerned about what’s happening and it’s not because we have TDS or we’re extreme liberals. Give us an answer.
