Friday mailbag!

Let's do this.

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Happy Friday!

We made it!

I want to get to what’s on your mind but before I do, a few favors (if I might):

1. I started an all-sports Substack called “The Replay” a week ago. If you like sports — and especially if you like sports nostalgia — I think you will dig it. In honor of Opening Day on Thursday, I ranked the 10 best baseball movies of all time. All of the content is free right now. Try it out!

2. I am posting daily political videos on my YouTube channel. You can check them out here. And subscribe!

Ok, self promotion over! Let’s get to your questions.

Q: Hi, Chris. As a native Nutmegger, I wanted to ask you what Joe Lieberman's legacy and impact.

A: I wrote about one aspect of Lieberman’s career — the time he was almost John McCain’s vice president — here.

More broadly: Lieberman was a political legend in Connecticut when I was growing up. That reputation only grew when Al Gore picked him on the national ticket in 2000. Connecticut boy makes good — and all that.

If Lieberman’s story ended after that 2000 loss, his legacy would be unquestioned: A historic (first Jewish VP candidate) politician. Period.

But, well, his career didn’t end there. He ran an embarrassingly bad bid for the Democratic nomination in 2004 — his claim of a three-way tie for third in the New Hampshire primary (he finished 6th) is still epically terrible — that proved that his brand of moderate politics was not where the party was headed.

Two years after that, he lost the Democratic Senate nomination to Ned Lamont (now the state’s governor) but ran as an independent in the general election — and won.

By 2008, Lieberman’s political evolution was nearly complete. He spoke at the Republican National Convention, endorsed John McCain and went after Democratic nominee Barack Obama. Which was quite a turn — even knowing that McCain and Lieberman were personally very close.

Lieberman was, by that point, a loathed figure among liberal Democrats. He only made that worse when he aligned, late in his life, with No Labels, the group looking to field a third party alternative to Donald Trump and Joe Biden.

So, I tend to think of Lieberman’s political life in two distinct eras: The Democratic one (1988-2004) and the, uh, not-so-Democratic one (2006-2024). How you feel about those eras very much depends on your partisan affiliation.

Like him or not, I would say Lieberman was, personally, a lovely man. He was kind and generous. Read this from Mark McKinnon on Lieberman the person.