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I thought the rise of Donald Trump would be great for Jeb Bush. Wow, was I wrong.

Charlie Leight/Getty, Kayana Szymczak/Getty

Last summer I wrote an article for Vox headlined, "Donald Trump’s rise is great news — for Jeb Bush."

Yeah … that didn’t hold up so well.

The piece recently resurfaced in the wake of Bush’s withdrawal from the race, and yesterday many of the political set I follow on Twitter shared a good laugh together about how hilariously, terribly wrong it turned out to be.

Now, I must admit I felt a bit resentful about being judged by one wrong article. After all, I jumped off the Trump skeptic train shortly afterward — last September I wrote, "Political scientists think "the party" will stop Trump. They shouldn't be so sure," a long essay in which I made the case that the "party decides" thesis was weaker than many believed. Where are the tweets about my smart call?

But that's not how the internet works — nor should it, really. The piece on Trump and Jeb was dreadfully wrong, as was another piece I wrote that same month underrating Trump’s chances. I was, of course, in good company — the majority of political reporters and commentators also failed to anticipate Trump’s rise, and once that rise was unmistakable, many kept expecting him to quickly collapse.

So what did I learn from all this? A few things!

I fought the last war

First, I overlearned what seemed to me to be the lessons of the 2012 cycle. At various points during that GOP nomination contest, Rick Perry, Herman Cain, Newt Gingrich, and Rick Santorum all led national polls, and Michele Bachmann briefly led in Iowa. Even Donald Trump, who didn’t end up running, led a couple of polls in the spring.

Of course, all those who did run collapsed eventually, and Mitt Romney — the guy everyone expected it to be all along — won the nomination. In retrospect, the media frenzy over many of these candidates felt silly. They were never serious contenders, while Romney had it in the bag all along.

That’s the freshest presidential primary memory I (and everyone else) had going into 2016. So I assumed Trump was cut from the same cloth as the non-Romneys. If anything, I thought he was more obviously doomed. His affect seemed even more clownish, and he had no experience running for office and no chance of winning any party support. Candidates like that tend to lose!

Obviously, that turned out to be a terrible assumption. The recency of the 2012 case initially made me blind to the possibility that 2016 could be a quite different situation.

I also had some hindsight bias. I let the fact that Romney won shape my evaluation of what had happened beforehand. Viewed in a different light — with, yes, more hindsight — it actually seems rather remarkable that Santorum, a little-known ex-senator who lost reelection by 20 points and raised hardly any money, managed to win 11 states over the clear party favorite.

It’s easy to fall into the trap of blithely citing experts rather than skeptically analyzing what they're saying

Experts are great to talk to. It’s wonderful that smart people who know a ton about a subject are happy to share their views with journalists, to help flesh out an article.

But sometimes those experts can be wrong. And sometimes we writers who cite them can oversimplify their findings, or can misapply their general findings to particular cases.

We don’t yet know how the 2016 election has turned out, so we can’t have a final verdict on the "party decides" thesis just yet. But I think the verdict on how the thesis affected a certain subset of political writers is already clear — and it’s not good.

The phrase became a certain savvy shorthand, a proven truth about "how things really work" that the old media was just too blind to see. But in that, it became its own sort of conventional wisdom. And it was often used as an excuse to cut off lines of inquiry rather than explore them — as I did in the Trump/Bush piece, when I simply cited party elites' influence over the nominations as the reason Trump obviously couldn't win.

This is no reflection on the Party Decides authors’ work — they wrote their book as a work of scholarship, not as ammunition for pundits. Their argument in fact has a host of caveats and uncertainties that I later found fascinating to explore in my longer essay. I also found that the authors themselves are quite open-minded and willing to explore how they might be wrong.

But delving into those complexities takes a lot of time and effort. It’s much easier to just quote what an expert says or endorse a popular expert idea. So I and other commentators who frequently cited The Party Decides should have done a better job at making our audiences aware of these various complications to the authors’ theory early on, rather than just quoting it as an authoritative resource. If we had done that, we wouldn't have been caught so flat-footed by what's unfolded in the Republican race.

Selective reporting can lead you astray

Though my piece on Bush and Trump wasn’t specifically reported out, one of the reasons I overrated Bush’s ability to benefit from Trump’s rise was my past reporting. No, it wasn’t that I was spun by Jeb’s campaign staff — they never gave me the time of day. Instead, I had spent a great deal of time interviewing people who knew Bush from Florida, and researching his life and career, for a June 2015 profile.

While that profile in fact concluded by suggesting that Marco Rubio might better appeal to GOP voters this cycle than Bush, I did come away impressed by what I learned about Bush’s political acumen. He seemed adaptable and resourceful, having remade his political persona after his 1994 loss to become a popular two-term governor. The Democrats I talked to feared him. And I learned that, yes, he most definitely did have a super-conservative record.

So when Trump soared in the polls, I fell back on my understanding of Bush from his Florida days, thinking the savvy pol could adeptly turn the rise of Trump to his advantage. His operation did have all that money, after all!

Yet at that point I had never similarly delved into Donald Trump’s background. He seemed like a carnival sideshow to me. Perhaps if I had tried to learn more about him early on rather than dismissing him, I would have learned not to underestimate his own ability to win a political knife fight. (But perhaps not.)

Check your assumptions, and explore counterarguments

Back in that now-infamous piece on Jeb and Trump, I proclaimed that the former governor would benefit from the billionaire's prominence. But, of course, I didn’t really know that. Instead, I was making an argument that I thought, at the time, was a very plausible and well-supported one. And I wasn't alone in this — some very smart commentators came to similar conclusions.

Yet in crafting that argument, I focused too much on justifying why it was probably true, and not enough on exploring reasons I could be wrong or checking my underlying assumptions.

Anyone writing about the election has a certain set of assumptions that shape their understanding of what is happening and what they think might happen. Sometimes those assumptions are implicit, sometimes explicit. And one assumption I started with, which was also widely shared in the press, was that Donald Trump couldn't win. It was an assumption that went unquestioned for too long, and it helped shape how I and many others covered the race.

Now, when it came to Trump versus Jeb, could I have ever expected that Trump would so memorably dub Bush "low-energy"? Of course not. But it was certainly possible to anticipate that Trump would go after Bush hard on immigration and that that could greatly damage Bush in the primary. An obvious counterargument like that should have tempered my seeming certainty about how the Trump-Bush rivalry would turn out.

So it's always good to check yourself, to explore uncertainty, and to carefully consider how you might be wrong. When it comes to predicting the future, my article — and, really, this whole election — has been a good reminder that some humility is in order.

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