Tom Steyer. (Jahi Chikwendiu/The Washington Post)
Opinion writer

The 2020 presidential campaign could see not only the largest field of Democratic candidates in history, but also one of the most fascinating and revealing primary campaigns in a long time. The politics of presidential nominations have changed dramatically, driven by the success of the last two presidents: Barack Obama proved that if you’re compelling and charismatic enough you don’t need to have a long tenure in office, and Donald Trump proved that pretty much anybody can get a party nomination given the right set of circumstances.

That has led dozens of Democrats to ask themselves, “Why not me?” The latest potential candidate is Tom Steyer, who has made himself into the most important Democratic donor despite the fact that few Americans who aren’t political junkies have ever heard of him:

Tom Steyer, the California billionaire best known for his campaign to impeach President Trump, is making a move toward a potential 2020 White House bid, launching town halls in key primary states on the platform of “five rights.”

Steyer announced the move Tuesday on his website and with a full-page ad in newspapers across the country. His “five rights” focus on education, the environment, voting rights, the economy, and health care. …

Tuesday’s launch also includes a six-figure Web ad buy on Facebook, YouTube, Twitter and Instagram, Cavalier said.

The fundamental question the Democratic Party is going to be asking itself in 2020 is, “Who are we?” Or more specifically, “Which candidate best expresses who we are?” This question lies underneath every presidential nominating campaign, but in some campaigns it’s more important than in others. It was a key question in 2008, and Obama won because he was the answer to that question, or at least an aspirational version of that question. Democrats saw in Obama not only who they were but also who they wanted to be: sophisticated, urbane, intellectual, cosmopolitan, thoughtful, multiracial and charismatic. For once, they stopped asking themselves who was “electable” — i.e., which candidate would be attractive to other people — and asked which candidate they were most drawn to. It worked out pretty well.

Could Steyer be that person in 2020? I’ll admit that I start with a bias against billionaires who think they should be president. The super-rich tend to live in a bubble in which everyone is constantly telling them how brilliant they are, which helps to convince them that because they succeeded in one area they can succeed in any area. In case it wasn’t clear before, Trump has shown that being president is extremely complicated and requires a range of skills and experience that you generally don’t have if you haven’t spent time in elected office.

Having said that, Steyer has shown a seriousness about his political project that most donors lack. He spent more than any other donor in the 2014, 2016 and 2018 election cycles — more than $226 million. But instead of just throwing money at a bunch of political consultants who waste it on pricey TV ads, he spent those years building a political machine. His two organizations, Need to Impeach and Next Gen America, are vehicles for engaging liberals, and just as important, assembling lists.

Whatever you think about the impeachment question, they claim that 6.3 million people have signed on, which is a pretty healthy group of supporters to start with. Put together, the organizations have hundreds of staffers, have worked on the ground in states all over the country doing voter registration and advocacy, and have built partnerships with a host of other liberal groups.

In other words, Steyer isn’t messing around. But we have no idea how he would perform as a candidate if he chose to give it a shot.

A presidential candidacy is many things. It’s a management challenge, building an organization that has to go from zero to light speed faster than any corporation ever has to. One day you can have a dozen staffers in a couple of ratty offices in Iowa, and a month later the enterprise has grown to hundreds of employees spread across a dozen states trying to coordinate their activities in an environment that changes every day. It’s a strategic challenge, requiring one to devise a path through a complex electoral process and a message that will persuade voters. It’s a personal challenge, testing the candidate’s stamina, his ability to persuade and his capacity to weather the inevitable crises.

And particularly when your party’s voters are enraged by the current president and eager for a true champion — as Democrats were in 2008, as Republicans were in 2016 and as Democrats will be again in 2020 — it’s an emotional challenge. The winner will have to connect with voters on a level that reaches down where their identities lie, to tap into their hopes, their fears, their desires and to embody everything they want their party to be.

None of us have any idea whether Tom Steyer can do that, any more than we know whether Elizabeth Warren can, or Kamala Harris can, or Cory Booker can, or Kirsten Gillibrand can, or any of the other 50 or 60 Democrats considering a run can. I do think that any white man is going to have an extra hurdle to overcome in saying “I will be the embodiment of this party” when the party is not only more diverse than ever but also sees that as its greatest strength in the future. But it’s going to be a fascinating contest.

Read more:

Katrina vanden Heuvel: How Democrats can turn up the heat on Trump — and win the battle of ideas

John Emshwiller: I thought Democrats would appreciate my first-ever donation. I was wrong.

Megan McArdle: Can out-of-state money swing elections? Don’t Beto on it.

Ruy Teixeira: The midterms gave Democrats clear marching orders for 2020