Who’s the Jeb of the 2020 Race?

Hi. Welcome to On Politics, your guide to the day in national politics. I’m Matt Flegenheimer, your temporary host. Lisa Lerer is on vacation, beach-reading Mueller report footnotes.

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On paper, I’d hit the candidate jackpot.

It was 2015 — many months before President Trump had won a single vote — and my campaign assignment couldn’t be beat: I would be covering the front-runner. The juggernaut. The one whose name they’d chant at the convention hall.

Ladies and gentlemen, the 45th president of the United States …

So, plans change. But a funny thing has been happening lately in conversations with people close to the 2020 race: Jeb Bush is on the brain again.

Not because he’s running, a prospect with the approximate likelihood of a third term for Grover Cleveland.

But because those who are running may have more in common with Mr. Bush than they’d care to admit.

Across the Democratic primary field, candidates hoping to avoid his fate — high hopes, “low energy,” hard fall — are finding themselves in familiar political minefields, even if they’d rarely agree with Mr. Bush on policy.

The most conspicuous parallel is Joe Biden, who is expected to enter the race this week as a Jeb-style early favorite, carrying high name identification, uncertain base-voter enthusiasm and heaps of baggage into a political moment that may have passed him by.

But there are also less intuitive comparisons.

Like Mr. Bush in his race, Elizabeth Warren is the clear leader on policy in her primary, churning out proposals but struggling to gain traction in early polls. She is also spending heavily on staff, as Mr. Bush did, outpacing any other campaign despite her middling fund-raising numbers. (Mr. Bush ultimately needed to slash salaries and headquarters staff.)

When I noticed a T-shirt available on her website recently — “Warren Has a Plan For That,” it reads — I flashed immediately to one of Mr. Bush’s particularly ill-fated slogans: “Jeb Can Fix It.”

Then again, maybe Beto O’Rourke is the cleaner analogy — another son of a politician who has faced skepticism for his privileged rise and was coaxed into the presidential contest not by any signature ideological cause but because, in Mr. O’Rourke’s words, he was “born to be in it.” (Of course, the silver spoon critique applies more credibly to Mr. Bush, who shares a surname with two presidents, than to the child of a former El Paso County commissioner.)

For more moderate figures in the Democratic field, like John Hickenlooper or Amy Klobuchar, Mr. Bush’s inadvertently prescient warning about the political perils of centrism could also prove relevant. Before entering the 2016 race, Mr. Bush suggested that the eventual Republican nominee would need to avoid being pulled to the partisan extreme to remain palatable…

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