Friday mailbag!

Your questions, answered.

As of today, I have been writing this newsletter for a month. It’s been a really gratifying experience for me — a chance to build a community from the ground up and experiment with format and style.

To date, everything in the newsletter has been free. I am going to start putting some content behind a paywall going forward — although I am committing to keep a good chunk of stuff free for people who can’t afford to pay.

I hope you’ll continue to support this endeavor as I keep trying new and different things to bring the best experience to you. If you like what you are getting, please spread the word to other people you think might be interested.

And, in case you didn’t know, we are almost two months to the day away from my book coming out! It’s called “Power Players: Sports, Politics and the American Presidency.” I am super proud of it. You can read an early review of it here and pre-order it here!

Ok, let’s get to your questions!

Q: As a Canadian I find American style politics interesting to say the least, and because I have followed your reporting for some time now I am wondering what you think the American Founding Fathers would think of how their original words are being interpreted today? In particular the right to bear arms and freedom of speech. Canada has its own warts and is constantly revisiting its history - sometimes to our own detriment - but I find it strange the SCOTUS for example often refers to the drafters’ original intent. Do they have a direct line to the afterlife?

A: I think one of the biggest challenges with the American Constitution is whether you take it all literally or whether you take it as a document of its time that was intended by the founders to be interpreted and reinterpreted to fit our modern moment.

For me, it is hard for to imagine that the Founding Fathers imagined that technology would produce something like an AR-15 — a gun that can commit mass murder in a matter of seconds. And that the 2nd Amendment would be used as a way to justify peoples’ right to own those guns.

At the same time, I DO think there is value in traditions that sustain over decades and even centuries. I think there’s real value that the House and the Senate — and the broad rules that govern them — are largely unchanged since the founding of the country.

I guess where I come down on it is an appeal to common sense. To me, using the 2nd Amendment as a way to justify there being more guns than people in the country is way over the top. At the same time, I wouldn’t want to throw out all traditions of American government just because some feel entirely anachronistic.

Q: Let's talk about ageism, the last acceptable prejudice. On CNN Don Lemon dismissed a clip of James Carville with, "Pass the salt, grandpa." Nikki Haley proposes that presidential candidates "over 75" be required to take a mental health test. Your sensitive post about Dianne Feinstein notwithstanding, how do you think bashing people because of their age plays with the electorate?

A: Man, another TOUGH question.

Look, scientific developments means we are living longer and longer — and are more and more able to function at a high level even as we age.

And so, I do think there needs to be some adjustment of what “old” means in society. My mom is 75 — and I don’t think of her as “old.” She still gets around well, is super engaged in the news (she reads the whole Washington Post every day) and is showing very few signs of slowing down.

When it comes to our politicians, I think we should have a slightly different — and higher — bar on age. In the case of Feinstein, she is one of two Senators representing a state that has almost 40 million residents. There are several stories documenting the fact — via fellow senators — that she has a lot of short term memory problems. Given that, I think it’s fair to ask whether she should serve out her term or whether she should resign so that someone else can represent the state for the next year and a half.

It’s SUCH a touchy subject. And I am not sure there is a single best way to handle the age question across society — or even in politics. I think it’s a case by case question.

Q: Are Florida, Missouri and Ohio "lost forever" to the Democrats? It sure seems that way to me, as an outsider.

A: The one BIG lesson I’ve learned in politics is to NEVER say never when it comes to what might happen in the future. (At some point in mid 2015, I proclaimed that Donald Trump would never be elected president. See how that one worked out…)

There’s no question that over the last 20 years all three of the states you mentioned have moved clearly toward Republicans — largely due to the white vote consolidating behind the GOP.

(I still remember the 2000 election when Ohio and Florida were seen as THE swingiest states in the country.)

To me, Florida remains a potentially competitive state over the next 10-20 years as the Hispanic population continues to grow and the white population continues to age. I think Ohio and Missouri are going to be tougher for Democrats.

Q: Hi Chris, I love your thought processes and your philosophy of the political world. That being said, politicians (namely Biden, Pence, Haley etc). keep saying something along the lines of “I am so optimistic about the (USA) future, the best is yet to come.”

Really ???? So do you think they believe that ???

(While others : Trump, Cruz, Jordan, etc all assure us that we’re going to Hell in a Handbasket.

Do they believe that ???

(Or are all pols just helpless liars?)

A: Ha! Yes, political rhetoric has gotten totally out of control. Or maybe it’s always been out of control!

I think most politicians running for national office — Donald Trump excepted — feel as though they need to paint an optimistic vision of the future. The idea being that people want to vote for someone who will make their lives better and who has a plan to make that happen.

Trump is a very weird exception to that general trend. His vision is decidedly dark — the country is going to hell and only he can save it. That sort of “savior” message worked for him in 2016 but was a harder sell when he was the sitting president in 2020. He appears unbowed though. Everything I see him say these days is premised on the idea that the United States under Joe Biden is an absolute hellhole.

Q: What are your thoughts on Rep. Ralph Norman's endorsement of Nikki Haley? I was a bit surprised that's who he ended up endorsing.

A: I think they’ve known each other going all the way back to the South Carolina legislature so I wasn’t shocked. I also am VERY skeptical that the endorsement of Ralph Norman matters a whit to Haley’s chances in South Carolina or anywhere else.

My basic view is that, especially in a presidential primary, endorsements are WAY overrated. With very few exceptions — Jim Clyburn being one — I think a congressional endorsement makes for a nice press release or tweet and that’s about it. I just don’t think voters in this day and age are persuaded to vote for you because some other elected official says they should.

Q: How much should we fear Ron DeSantis? Do you think he'll be a radical candidate and continue his anti "woke" agenda on a foreign policy level? Some fringe voices on the right have suggested leaving the UN, could DeSantis embrace an idea like that in order to show his anti "woke" credentials to the base? Or otherwise adopt a fully isolationist stance?

A: Hmmm.

So, I think that if you are a Democrat, DeSantis is a far scarier general election candidate than Trump.

Here’s why: Joe Biden’s biggest weakness (and this isn’t going to change) is that he is 80 years old — and will be 82 shortly after the 2024 election.

The best way to take advantage of that weakness is to nominate someone who represents a generational change from Biden. Trump, at 76, doesn’t do that. DeSantis, at 44, very much does.

I also think while Trump struggles to stay on message and just sort of does whatever he thinks is best for him in the moment, DeSantis is far more strategic and plotting about what he says and does.

All that said, I think it very much remains to be seen how DeSantis stands up amid the deep vetting he will get as one of the favorites for the Republican nomination. If he winds up as the nominee — which would mean he survived the vetting gauntlet — I think he would be a formidable challenge for Biden.

Q: Chris, given how close recent elections have been, I find it almost unbelievable that Reagan got 525 (of 538) electoral votes as recently as 1984. I'm saying nothing one way or the other about Reagan , just the idea that we could all agree to that extent on anything is amazing given the hyper-polarization today. Do you ever see anything like that happening again?

A: It is pretty remarkable. No question.

As for whether it could ever happen again, I will refer back to my answer above about never saying never.

What I can also say though is that I would find it very hard in the near-ish future (next 20 years or so) to see an electoral map that looked anything like Reagan in 1984.

We are just so polarized that there is about 45% of people who will never vote for a Democrat for president and another 45% who will never vote for a Republican for president. Which virtually ensures that Democratic-leaning states go Democratic and Republican-leaning one go Republican.

I think the new bar for a “landslide” should be Barack Obama’s 365 electoral votes in 2008. Obama won virtually every swing state that year — and managed to win in places like Indiana and North Carolina. To me, that’s about the ceiling of where any candidate can get to in the foreseeable future.

Q: This question may require you to look into a very unclear crystal ball, but I'll give it ask anyway. Looking at were likely to have two men who are in their late 70's to early 80's as the candidates for President in 2024, which party do you think is setup for long term success both with their bench candidates as well as policy ideas?

A: I actually think Republicans have more young talent — some of which will be on display in the coming presidential election. DeSantis, as I mentioned above, is 44. Nikki Haley is in her early 50s. Democrats will likely have to wait another four years for the like of Pete Buttigieg (still only 41) to step fully onto the national stage.

Up until this year, Republicans were much younger on the House leadership front — but the swapping out of the entirety of Democratic leadership for people two generations (at least) younger changes that equation. Hakeem Jeffries (52 years old) is likely to be speaker one day.

On the policy idea front, I think it’s more of a mixed bag. I am still waiting for some figure in either party to emerge like Bill Clinton did in the the late 1980s/early 1990s with a Third-Way-like set of policy proposals that aims to break the partisan deadlock.

Obama did some of this, for sure, but, obviously, he can’t be president again so Democrats are out of luck there. Honestly, I don’t see a ton of new ideas from either party these days.

Q: Favorite band / musician?

A: For the last few years, I have been WAY into The Hold Steady and frontman Craig Finn’s solo stuff. He doesn’t even really sing, it’s more like spoken word but I really dig it.

Listen to this on The Hold Steady and this on Finn solo.

I still listen to a lot of Wilco. And REM. I really like a band called Wild Pink. For ambient music (which I have gotten really into) Brian Eno is the king but I also like Johann Johannsson, the American Dollar and Eluvium.

Q: Hi, Chris! I promise I ask this question with the best of intentions: You had a large platform at CNN and a lot of your columns often set off the usual people on Twitter who live to be outraged and your name would be trending. Is it nice having this new outlet where you won't be the center of attention or do you miss the spotlight?

Also, it's time for you to return to Meet the Press roundtable.

A: A little of both?

I really enjoyed the massive platform that CNN afforded — and never took it for granted.

But, writing this newsletter has also scratched a long-standing itch for me — I can write about whatever I want whenever I want to. And it’s really nice to be able to interact with people on a one to one basis again.

So, like everything: New challenges create new opportunities!