Because Tinyletter is mostly for mail, it’s nearly impossible to find old newsletters. So I’m posting all my old newsletters here so they can be searched, indexed, all that. You’re still better off just subscribing.

Leona Helmsley died at the age of 87 on August 20, 2007.

August 20, 2016

ne year ago this Monday, I traveled to Mobile, Alabama, to cover a Donald Trump rally. This is the piece I wrote about it. I’m pretty pleased with how that piece turned out; I was given a lot of freedom to do it right, and not to have to turn it into the sort of You’ll Never Believe What Donald Trump Said Today piece that has dominated all media coverage of Trump in the year since. Frankly, it’s not the sort of piece that even Bloomberg Politics would run today. It can be tough to tell how to cover an election like this one. This election cycle has turned a lot of people into something they wouldn’t have recognized 12 months ago. It gets in your head.

It was sort of happenstance that I got to cover the rally anyway. My editor called me at, like, 7 p.m. and said that, for reasons no one in the office could figure out, Trump was randomly flying to a college football stadium — South Alabama’s, actually — the next day, and I was the only reporter they had “in the area.” Now, Mobile is in fact a six-hour drive from Athens, a rather far jump from “in the area,” but I understood: In offices like Bloomberg’s all across New York City, “the South” is basically one big neighborhood. I was ecstatic to get the assignment. This was still in the early days of Trump, just a couple of months after he announced, when he was doing all sorts of eccentric things that seemed charmingly befuddled rather than increasingly terrifying.

(I’m in that photo above. Can you find me?)

One of the odder notions of Trump’s appearance was that he was going to be in Alabama at all: How in the world would this billionaire (maybe) germophobe from Queens with the gold-encrusted throne in which he would behead wives once they reached a certain age appeal to poor voters in the rural South? The answer to this is obvious now but was quite the puzzle back then. And while Trump’s rallies would get intense and dangerous later on, particularly for journalists, I had no such issue at the rally. Everyone was extremely friendly — one section of my piece involves several people finding a wallet on the ground on going through progressively more ridiculous measures to find the woman it belonged to — and not just welcome to answer all my questions, but in fact quite eager. I could barely finish one interview without people lining up to be next.


People at the rally loved Trump, but most of them admitted they didn’t think he’d actually become President, or that he even wanted to be. This was all just for fun. And it was fun. It wasn’t ugly, not yet. There was a festival vibe to the place that was more festive and curious than committed and fervid. People dressed up like Trump, and a band played “Trump” to the tune of Van Halen’s “Jump.” (Not particularly well, I hasten to add.) A woman I went to high school with recognized me and flagged me down; she’d been on vacation nearby with her family, saw that Trump was speaking and figured why not? “It’s something to do,” she told me. “It’s different than just going to the casino again.” There were a couple crazies, but not many, and they were mostly ignored by the rest of the crowd. They were just there to have a good time. There were there to be entertained, and Trump was entertaining! It was a hot night in Alabama in August. What else is going on? Beats just going to the casino again.


I had a great time at the rally. I got tons of good stuff to write about, I met some nice people and I felt that Trump had captured something real and powerful, not something quite powerful enough to take him to the Oval Office but powerful enough that people should start paying more notice. It did not make me feel worse about the country. Heck, some crazy rich guy from television decides to run for President and some people who feel they never get a chance to be heard start to get behind the candidacy. That’s democracy! It’s good for us: That’s how it’s supposed to work! I liked the surreal nature of it all: A little shot of lunacy might be exactly what we need sometimes. The piece ends with this line: “There are currently five, maybe six people on this planet who have a chance to become the next leader of the free world, and you are kidding yourself if you do not believe he is one of them.”

I got mocked quite a bit for that one. I am not mocked for it anymore. Not that it necessarily makes any of this any easier.

When I see the corrosiveness of Trump’s campaign, the way that it forces us, to be entirely honest, to face so many of the ingrained personality traits of this country that I often try to pretend to myself don’t exist, I try to remember that night in Mobile. Nice people. Good people. Cheerful people. There wasn’t any hate or anger then, at least not in those stands, not any of the people I talked to. I’ve been to two more Trump rallies since then. They were not the same. They were tenser, more fraught with palpable danger. From what I understand, it has gotten worse since then. Trump may lose this election. He probably will. But already it feels sort of different. Already we feel sort of different.

But I swear: The people there were good. They really were. Have they changed in the last year? Or it is everything around them?


People have been asking me how much I’ve enjoyed covering politics in the last year. Lots of it has been a blast. I’ve worked with smart, talented people, and I’ve challenged myself, and I’ve gotten to write some stories I never imagined I’d have the opportunity to write. (Particularly in Iowa, the highlight of the cycle for me.) But I imagined, going in, after years of writing about sports and entertainment, politics would be ennobling. It would be a higher calling. It would be a way to write about something that matters, about Serious Things.

This has not been what has happened. I have written about candidate’s spouses being mocked for being ugly, I have written about bullying, I have written about two candidates vying for the highest office on the planet mocking each other for having small penises. I’m eager and anxious to see what happens these last few months. I’m lucky to have this opportunity. But it has not been what I thought it would be. I’ve talked to many political reporters who can’t believe how thrilling and unpredictable and exciting this election cycle has been, how it’s so much more fun than it usually is. I think I might have preferred those earlier, less exciting election cycles. I think maybe election cycles aren’t supposed to be this exciting.

Here is a numerical breakdown of all the things I wrote this week, in order of what I believe to be their quality. (This is an attempt to have an objective look at the value of my work in a way that I suspect will be difficult to sustain.)

1. Giancarlo Stanton and the Curse of Potential, Sports On Earth. This was one of those weeks where I wrote a ton of stuff, but most of it, you won’t read until later. So it looks like it wasn’t that busy of a week. Trust me, it was.

2. A Fantasy Football Guide For Old People, Sports On Earth. I know I turned 40 last year, but as Daulerio has always reminded me, I’ve basically been obsessed with feeling old for 15 years. I’m going to enjoy being a cranky old writer, I think, when I actually do get there. (Wait: Am I already there?)

3. Royals Fans Are Still Enjoying Their Long-Awaited Championship, Sports On Earth. I also took a 19-hour trip to Kansas City this week and saw my old friend Matt Pitzer. Matt thinks I’m writing too many words in the intro to these newsletters, and he’s probably right. But hey: Can’t stop, won’t stop!

4. Thirty Stunning Factoids From MLB’s Second Half, Sports On Earth. 30! That many!

5. The AFC South Carries a Bunch of What-Ifs, Sports On Earth. Yes, I picked the Jaguars. I regret nothingggggggg!

6. Our Jersey Bracket: The Elite Eight, Sports On Earth. Darn elites.

As I say every week: If you are the sort to subscribe to a weekly newsletter, I would have to think it wouldn’t be too much of a hassle to subscribe to one of the four (!) podcasts I do. Here they are:

The Will Leitch Experience, my annual massive fantasy football preview with Yahoo’s Andy Behrens.

Grierson & Leitch, discussing six new releases, from “Pete’s Dragon” to “Sausage Party,” and then digging into Alfred Hitchcock’s “Rear Window.” (Turns out, Alfred Hitchcock was really good at making movies.)

Waitin’ Since Last Saturday, second show of the season, previewing every team in the SEC. Next week, we break down the UGA roster. I drink way too much bourbon at these tapings.

Culture Caucus, no show this week.

I’m flying out to New York beginning of this week to do two MLB Plus games. If you have, you can see me call both Monday night’s and Tuesday night’s Orioles-Nationals games. See? I’m a Beltway insider.