Newsletter 27: The Piece I Wrote on the Eve of the 2016 Presidential Election

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I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. Here is a newsletter from November 2016. It is the last newsletter I wrote before the election, trying to get down my thoughts about covering that election, about how stark the choice facing the nation was, about how I wanted my children to see where their father’s head was at on the eve of that election, when they went back to find out. Considering the events of the last week, and really the events of the last two years, I thought it might be relevant this week. This also remains the longest newsletter I ever wrote.

On Tuesday, the first Presidential campaign I’ve ever covered will come to an end. Now, I shouldn’t be so casual about using the word “covered.” Most political reporters, from the embeds who have been following each candidate from stop to stop for 18 months now to even the pundits who just travel from green room to green room all day, have far more right to the term than I do. I’ve simply written a few features and thinkpieces, co-hosted a political podcast, done a little bit of travel and yakked on television a few times. I mean not to insult all those reporters who have made this election their entire lives for the last 18 months. I have simply been dabbling.

But I have been paid to dabble: This is the first election in which following what’s happening has been a professional endeavor. It was sort of accidental how it came about. In the wake of the Sports On Earth bloodletting more than two years ago now, I was sniffing around, just in case that thing officially went fully sideways. (I’m proud to say now that Sports On Earth is healthier than ever, and I’m not sure I’ve ever had more fun at my job. But you may remember, back in August 2014, it got hairy there for a while.) I was talking to my old friend John Heilemann, with whom I’d worked at New York, and asked if they needed any help over there at Bloomberg, where he’d just been hired to start a political site and television show with his Game Change co-author Mark Halperin. (The whole thing was spearheaded by Josh Tyrangiel, the super genius who now runs the Vice news show on HBO but will always be best known to me for kicking my ass in fantasy baseball every year for the past decade.)

I’d always wanted to cover a political election, something John knew, and we sort of brainstormed up a beat. Basically, it seemed like the culture impact of a President election — what it did to art, and comedy, and the general mood of an American populace — could in fact be its own beat: How a candidate navigated the news media and popular media felt like something that would self-generate story after story. So we decided I’d come on as a consultant/contractor, working with my old New York editor John Homans, filing stories about that squishy space between politics and culture.

I couldn’t wait. I’d been covering sports and entertainment for more than a decade, but like a comedian who just wants to act!, I longed for more substantial work of deeper import. Sportswriting and film criticism? Blogging? Piffle! I would be doing the Legitimate work of political reporting. I would be taken seriously! Take that Bissinger! But it wasn’t just a careerist thing. Covering a Presidential campaign did seem important, and more so, I thought it would be ennobling. What could be more gratifying that writing professionally about the most important decision we make as Americans? After years writing about athletes and movie stars, I’d now be delving into things that matter. Goodbye, juvenilia and empty bunkum! The 2016 election would be something I’d be deeply proud to cover. Serious people talking about serious issues: The 2016 Presidential election would be my step up in class, discourse and gravity.

It did not turn out that the 2016 Presidential election was a step up in class, discourse and gravity.


I’ve written some stuff I’m proud of this election cycle, from this sad profile of Jeb Bush to the cop Woodstock that was the RNC in Cleveland to this ode to the political genius of Parks and Recreation to my trip to Mobile, Alabama to cover a Trump rally that felt like the first embers of what was coming. I’ve traveled to primaries and caucuses and debates and conventions and all sorts of places I never imagined I’d go. And this video segment I did during Letterman’s final week of shows is the most fun television thing I’ve ever worked on. I’ve been honored to have the opportunity to work with the Bloomberg Politics team, and John, and all sorts of geniuses over there, from Matt Negrin to Alex Trowbridge to Sarah Muller and many, many others.

Plus, I got my picture taken with The Bachelor.

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But I, like you, still can’t wait for this election to be over.

The reason, of course, is Trump. Call me part of the elitist whatever if you want, but I’ll confess, one of the reasons I was so looking forward to covering an election is that I thought it would be ennobling. I figured this would be a race between Hillary Clinton and either Jeb Bush or Ted Cruz or Marco Rubio, and it would be a (mostly) honest contest between two differing viewpoints on how best to handle the issues of the day. I am not a particularly dogmatic ideologue: I have my personal political views, but I’m don’t believe that they’re all that relevant or unique. Just because I have them doesn’t mean you have to hear them in my reporting: What I think about the issues of the day seems the least important thing I could include in a story. I mean, what the hell do I know? Thus, I looked forward to writing about these politicians as human beings, putting themselves through this insane ritual we ask of them every four years. I wrote a long feature about Rick Santorum that I think sums up my approach: Politics as a reflection of the soul. Who are these people? Why would anyone do this to themselves? The combination of egotism and idealism that makes up most politicians is fascinating to me. There are so many better ways to make money and gain power than this. Deep down, even the most craven politician can’t hide the fact that they started doing this because they cared. I couldn’t wait to write about the tension that happens personal belief comes into contact with the gnarled, ugly real world.

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I didn’t think it would be a problem to keep myself out of it at all. I liked Hillary Clinton, and I liked Jeb Bush, and I even sort of admired Ted Cruz: To be that influential and powerful despite everyone who meets you actively disliking you is a skill that you kinda can’t help but respect.

But then Trump happened. We all thought it was funny at first, and I’ll confess, the piece I wrote the day Trump announced — before we even knew what his announcement would be — is in fact complimentary of him (while dismissing him as a serious candidate). Here’s a section that holds up, I think:

Few people have been better at making people look at him, even when he has nothing to say, especially when he has nothing to say, than Donald Trump. The idea that he is somehow not a serious presidential candidate, that he doesn’t bring anything to a potential debate — a point of some importance this presidential cycle, considering that Trump’s name recognition is liable to qualify him for the debates — is completely immaterial. Trump flirts with running for president every cycle because he knows that it’s America’s greatest opportunity for personal branding, and if you think that’s somehow beneath the process, well, talk to the more than a dozen other people running for president this year who, like Trump, also have no chance to become president. They’re doing it for the same reason Trump does everything: They’re trying to increase their Q rating, whether it’s to angle for a veep slot or to push a pet cause or just to get a sweet lobbying gig in a few years. Why is Donald Trump’s fake-running for president to pump up The Apprentice ratings or to help him get a better table at Le Cirque any different, or worse, than Bobby Jindal doing it to get a Fox gig, or Martin O’Malley doing it to get Hillary Clinton to look at him as a potential V.P., or George Pataki doing it for whatever weird reason George Pataki is doing it for?

All right, so maybe he had a better chance of becoming President than I thought, but otherwise: That whole piece — in which I spent the first three paragraphs talking about my late grandmother — still feels strong and true. But I take no pride in this. Because I’m not sure there has ever been a candidate for any office ever that I have reviled more than Donald Trump.

This is not something you are supposed to say as a journalist. (This is not something I’m comfortable with even as a human. I don’t revile anything! To each their own! More power to you! You do you!) One of the reasons Trump made it this far was that so many other journalists fell into this trap, this professional obligation to treat Trump like he was a normal candidate when he was anything but. The problem with Trump, my problem with Trump, is not that he has different stances on the issues than I do, or you do. The problem isn’t even, necessarily, just that he is a bigot and a misogynist and a brute. (Those qualities, repugnant as they are, don’t make him unique among politicians, or humans.) The problem is that he has no idea what he’s talking about. We have all watched this guy every day for 18 months and even the people who are going to vote for him — and there are millions and millions of people who are going to vote for him — would not argue that he has even the most cursory understanding of what the job of President entails. Each of the three debates — each one! He never got better! — was an exercise in watching a man scramble for answers to a test he had not studied for. (Here is the best of dozens of examples.) This is a person without a clue of what he’s talking about.

Now, in a vacuum, for just a regular person walking around, this is no big deal. I couldn’t answer most of the questions in a debate either. But I am not pretending that I could be President. This is a person who not only does not understand basic public policy, he has shown not the slightest bit of curiosity about learning.

Actually, now that I’ve typed that paragraph, I feel obliged to clarify: That’s not the thing I dislike most about Trump. Here are the things that are the worst about this man running to be the most powerful person in the world:

He has lowered the level of discourse. Remember earlier when I was talking about politics being “ennobling” compared to sports and entertainment? Well, not once, before this election, have I ever had to write about an event in which one of the participants bragged about his penis size. Very ennobling! I can’t think of a worse message we could send to kids that to give them a Presidential election that is, in fact, inappropriate for them to talk about in class.

He’s not only a bigot, he encourages bigotry. I believe people are inherently good, but that they all have evil inside of them, me, you, all of us. What Trump has done is cravenly appeal to that evil for his own personal benefit. When someone runs for President, the microphone that comes with that position has incredible power. Trump has encouraged our darkest thoughts and, worse, made them seem acceptable in the public arena. Trump has done everything he can to break down our civil society, all in the name of his own advancement.

He doesn’t pay his contractors. It’s one thing to haggle on price to get a better deal. It is another thing to stiff people simply because you can. The central organizing principle of my life is work, that work is what makes the world go around: It is what I respect in a person, deep down, perhaps more than anything else. That Trump would refuse to pay people who have done work for them for no other reason because he thinks he can get away with it shows a blatant disregard for what we once considered our fundamental American value, and advantage.

He has no respect for women, which he means he has no respect for the human race. I don’t claim to be, or want to be, any sort of white knight: Women don’t need me to launch into some sort of rhetorical battle to protect them. But honestly: I don’t see how anyone who has any sort of respect for any person on this planet can hear how Trump talks about women and believe this person should be in charge of anything larger than an empty cardboard box. Trump is the sort of guy I was raised to think needed knocked on his ass.

He might just ruin the world for my kids. I’m 41 years old now, which means my life is almost certainly half over. I’ve had plenty of opportunities in my life: I’ve gotten my shot. You can make any decision you want that I disagree with, and I won’t raise too much of a stink about it: I’ll be fine either way. But my kids, I, you know, sort of need the world to still be around for them. People talk about your perspective changing when you have kids, but I didn’t quite understand that it would make me care about everything more than I used to: There is nothing charming or amusing or appealing about Blowing All The Shit Up, or Draining The Swamp, anymore. Parenting makes one a lot less of a nihilist. I need someone who won’t f — k up the world for my kids.

In all honesty, if you were to genetically construct a person who represents the exact opposite of what I believe about the world in every possible way — and I’m not even talking about political issues here; I’m not sure anyone, including Trump, even knows enough about his true beliefs to find something to agree or disagree with — it would be Donald Trump. I truly believe that we would be better off sticking our finger in a phonebook and electing whatever name we landed on.

I don’t like doing stuff like this. I dislike dogma, and Hot Takes, and I know better than you do so listen to me rants like this, as I hope anyone who knows my work well enough to subscribe to a newsletter already understands. But in 30 years, my kids are going to read about the time that Donald Trump ran for President, and they’re not going to believe it could have possibly been real. Who could have fathomably been for him? Wait … was Dad for him?

It is important for them to know that Dad was not. It is important for them to know that just because Dad was covering politics that year and therefore felt his personal beliefs should be absent from his stories, it does not mean that Dad didn’t feel as powerfully about this as he does much of anything in this world. Dad needed this on the record, in case he gets hit by a truck: He rejects everything Donald Trump stands for in the strongest possible fashion. He’s in fact deeply embarrassed that this is happening at all. He’s honestly glad you kids are too young to understand what’s going on.

I’m voting for Hillary Clinton. I like Hillary Clinton. I do not believe she is the simply the least worst of two bad options. I saw her at a South Carolina event in February with Gabby Giffords and the mothers of Trayvon Martin, Sandra Bland, Eric Garner, Jordan Davis and Dontre Hamilton. What I found noteworthy about her was how little she spoke. Those mothers, still blinded with pain, didn’t talk about Hillary’s views on the issues. They talked about how Hillary was there for them in an emotional way, how she understood their pain in a way that seemed to have nothing to do with politics at all. I don’t know if that’s true or not. I am skeptical enough of politics not to entirely believe it. But who gives a shit what I think? Those women weren’t lying. They were walking open wounds, and they all, one by one, spoke how she had privately consoled and counseled them. They spoke, and Hillary just listened. It was quite moving. I hadn’t needed a push to vote Hillary. But that turned my vote from a begrudging one to an enthusiastic one.

But this election, from the beginning, has been about Trump. We cannot let this damaged person be our leader. I have never cast an easier, or more vital, vote, and I suspect I never will.

I am sure that this little essay won’t change a single mind either direction, and I do not expect it to. I just wanted to make sure that, before this election ended, I got my stance on this on the public record. It might not matter to anyone but me and my family, and all told, it might not even matter to them. But I needed to say it before it was too late. So here it is.

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Written by

Writer, New York, NYT, MLB, WaPo, others. Founder, Deadspin. Author of four books, with fifth, “How Lucky,” coming May 2021.

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