Ten Years a Trumpwatcher

From cruise ships to cruise missiles, a decade of chaos, compromise, and column-writing in the Age of Donald.

Greetings from the Caribbean, where my wife and I are allegedly on a “working vacation.” This phrase, of course, is code for “trying to send one email while applying sunscreen to a screaming child’s face.” Hence, the drop-off in content.

Did I mention we brought our two sons? Because nothing says “relaxation” like refereeing slap fights in the backseat of a rented Jeep while trying to remember if the steering wheel’s on the left.

Here’s one of my sons (he’s on the right) with a new buddy we met during a three-hour tour that looked, at first glance, like a cross between JFK’s yacht days, a Vanity Fair summer issue, and a Vineyard Vines catalog.

Don’t be fooled. The only accurate detail is the shirt being on backwards — a small but telling nod to the overall vibe of disarray.

For those of us who aren’t #boatpeople, these excursions tend to evoke David Foster Wallace’s classic essay A Supposedly Fun Thing I’ll Never Do Again. Let’s just say this joins ziplining on my personal “once is plenty” list.

But I digress.

The larger point of this diversion — other than proving I’m alive — is to explain why I barely noticed a milestone that, under different circumstances, might have prompted a wistful blog post or bourbon-soaked podcast: Ten years of Donald J. Trump being a persistent, hulking presence in my professional life.

I’ve been a writer for twenty years. The first ten were about ideas, books, culture, politics. The last ten have been… Trump. Always Trump. Columns about Trump. Tweets about Trump. TV hits about Trump. Conversations about Trump. Trying, failing, and sometimes succeeding at understanding the Trump phenomenon — even as it dragged the media industry through a bizarre funhouse mirror.

But I recently dug up something I wrote exactly a decade ago — June 15, 2017 — back when “President Trump” still sounded like the setup to a late-night joke:

We teach our kids that being braggadocios is a vice, but for a people who feel beaten down, someone with a healthy superiority complex can be just what the doctor ordered…

People who have been deprived of a commanding leader — who have seen nothing but incompetence and impotence for most of their lives — may be susceptible to the charms of a man who flagrantly displays the trappings of power.

If confidence and competence are sometimes conflated, then Trump is in pretty good shape.

Not bad, in hindsight. Columnists have to take the W’s where we can. Most predictions age like milk. This one? Closer to a decent bourbon.

Fast-forward to today. Trump is somehow president again. (Yes, really.)

And while I warned that the cons of a second term would likely outweigh the pros, I did flag one hypothetical upside for certain hawkish conservatives.

This is from last November:

Trump might partner with Israel to cripple Iran’s nuclear ambitions… a bold move that could profoundly reshape Middle Eastern dynamics.

Prescient, eh? We’ll see.

Of course, that kind of realpolitik fantasy always looks better on paper than in practice. And military interventions tend to go sideways faster than a Carnival cruise in hurricane season. But still, there’s something oddly poetic about it: after a decade of chaos, scandal, and tweeting while governing, Trump might end up doing something... consequential.

Maybe even useful.

And if that sounds like a cop-out, it is. But after ten years of trying to make sense of the senseless, you stop chasing perfection — and start settling for upsides that at least sounds vaguely believable.

So here I am, a decade older, marginally tanner, and still writing about Trump — only now from the deck of a boat I didn’t want to be on, while pretending this is all still fun.

Some anniversaries call for cake. Others call for rum. This one?

Just pass the Advil.