The Wall Street Journal reports: “Former Texas Rep. Beto O’Rourke is asking aides to create an itinerary for him to take a solo road trip outside of Texas where he would ‘pop into places’ such as community college campuses, as he considers whether to enter the 2020 Democratic presidential primary, according to a person familiar with the plans.” Hillary Clinton called this a “listening tour,” but unlike Clinton, who was often sheltered from the press, “O’Rourke doesn’t plan to be accompanied by staff or press, though he may document the trip on social media and allow people he meets to do so as well.” Apparently he’s in no rush to decide whether to jump in.

O’Rourke’s assets are manifest. He’s an inspirational speaker and policy wonk, a fresh face, and a proven, phenomenal fundraiser. He’s got the “it” factor to thrill young audiences, but also the ability to talk to the full spectrum of Democratic voters.

O’Rourke’s biggest challenge is not the whisper campaign by acolytes of Sen. Bernie Sanders (I-Vt.) that he is a closet moderate (what’s wrong with that?!). O’Rourke is going to be in favor of roughly the same things (expanded health care, reenter the Paris climate accord, redo President Trump’s tax plan, reasonable gun safety laws) most 2020 aspirants in the field will favor; he’ll be against the same things (big money, PACs, the wall, special interests) that the others are against. Sure, he’s been savvy enough not to commit to single-payer health care and to point out that abolishing ICE is akin to rearranging the chairs on the Titanic (since the job has to be done by some entity). However, those who try to paint him as out of step with the party should look back at the 2018 midterms, when moderates won all around the country. (The Democratic base turned out in droves for candidates who weren’t the most progressive contenders in the primary.)

The real challenge for O’Rourke, I’d suggest, is twofold: 1) the toughness question; and 2) the Roger Mudd problem.

As to the first, the gangly, fast-talking former congressman will have to show he’s no pushover and not afraid to counterpunch. What’s he going to say when former vice president Joe Biden says, "Now son . . . " on the debate stage? How does he convince voters he’ll be able to stand up to Russian President Vladimir Putin — or Majority Leader Sen. Mitch McConnell (R-Ky.), for that matter?

In some sense, it’s the same challenge President Barack Obama faced in 2008. To an even greater degree, however, voters in 2020 are going to want inspiration but also tenacity — poetry but also grit. If they think Trump in all likelihood will be the GOP nominee, they don’t want their guy to be someone Trump can belittle and bully.

Obama overcame the toughness hurdle in part by sharing his compelling biography, the quintessential American success story of the child of a single mother who made his way to the Ivy League, the U.S. Senate and then to the presidential race.

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O’Rourke must find some means to show he won’t be cast as “Little Marco" by Trump (or, in less obnoxious terms, by his fellow Democrats). During his Senate race, O’Rourke was disinclined to go negative on Sen. Ted Cruz (R-Tex.), but by the debates he was able to deliver cool rebuffs and cutting retorts without seeming desperate. “He’s dishonest, that’s why the president called him ‘lying Ted,’ and that’s why the nickname stuck, it’s true,” he said about Cruz at one point. “True to form,” he said wryly when Cruz responded to a question about what he liked about his opponent with an anti-progressive screed.

One surefire way for O’Rourke to quiet skeptics would be, just as Obama did in 2008 against Clinton, to topple the big kahuna, Biden, should he decide to run. (Ultimately, it was toppling the Clinton dynasty that convinced voters Obama was ready to take on the Republicans and assume the presidency.)

The second challenge for O’Rourke is reminiscent of the infamous interview in which CBS anchor Roger Mudd asked Sen. Edward M. Kennedy (D-Mass.), “Why do you want to be president?” Kennedy hesitated, stumbled, rambled and never really answered the question. I have no doubt O’Rourke would be prepared for a similar question with a smooth answer, but the underlying question remains: What’s he got that no one else does, and why does the country need him rather than one of the two dozen or so other candidates?

Perhaps it will be some variation of Obama’s “there’s not a liberal America and a conservative America; there’s the United States of America” (the unifier), or of Bill Clinton’s “bridge to the 21st century” (a new generation of leadership). Whatever it is, he’ll need to keep intact over a two-year presidential campaign grind the same freshness, spontaneity and optimism he displayed in his Senate race. That will mean enduring a marathon race and pairing his sunny outlook with, when needed, a sharp elbow or two. It’s a tall order, but he may be the best natural politician in the field — and the best Democrats have seen since Obama took the country by storm.

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