There are a lot of ways to approach this question, but I like the method Matt Ygleisas, Laura McGann, and Dylan Mathews took in Vox recently where they looked at this question by saying who'd they "buy" (they're underrated) and "sell" (they're overrated) on the PredictIt betting website.
As I see it the Voxers, who are smart people who work for a good website, are a bit off to begin with when they announce, "It’s obviously way too early for anyone to have a realistic sense of who is going to prevail in Democrats’ large field of 2020 presidential candidates..." Sure, in the Age of Trump who really knows what will happen, but we can already draw some conclusions.
I don't know what to tell you about the Republicans these days, but in the Democratic Party it appears that party actors are still important and the "invisible primary" has been underway for quite some time. Indeed the gigantic Democratic Field has already been winnowed twice by my count with Jason Kander deciding to run for mayor of Kansas City instead of president, and New York Governor Andrew Cuomo basically bowing out of 2020 who with his "only caveat" which I'd say is a pretty Shermanesque statement.
In other words the Voxers are right about it being hard to pick the winner, but there's already a lot of ground to cover. My position is to sell Bernie and Biden and buy Martin O'Malley and Montana Governor Steve Bullock (this sounds insane I know but it'll make sense).
To make things simpler let's just go through by candidate as the Voxers rate them and I'll say what they get right and wrong:
- New York Governor Andrew Cuomo: Matt says sell. Makes sense due to him basically bowing out already.
- Washington Governor Jay Inslee: Matt says buy, makes sense, and please see my crazy O'Malley/Bullock theory outlined below.
- Joe Biden: McGann says time to sell. I agree, sell sell sell! But her analysis is all wrong. Biden's problem, and it's been basically the same thing since he decided to run for president sometime around 9:45 pm eastern on November 6th, 1984 is that the party loves him, just not for the top spot. McGann focuses on various "scandals" and gaffes to explain Biden's defeat that strike me as fairly similar to "But emails!" claims about Hillary Clinton. Likewise Biden's often bashed by younger liberal journalists like, well Matt Ygleisas about his length and "problematic" record. Which makes sense! Again the Democratic Party and politics in general have changed a lot since his shocking upset win against J. Caleb Boggs back in 1972. But that doesn't mean he;s not without his charms (progressive Vox journalists might hate him, but I love him, and yeah I saw him speak in person in a small room, it was amazing, shut up, you weren't there!) and a certain type of voter loves the man, but that same piece points out that Biden is going to "make a decision" about running around Christmas. Which means the man who ran for 30 years could give up the ghost. Or he could charge ahead and that would be a world in which in the invisible primary where, "What's left of his New Hampshire network, for instance, is fragmented, aging and undecided heading into 2020." Anyway feel free to sell.
- Tim Kaine: McGann claims Kaine is "a good buy at 2 cents" my response is, really? Don't get me wrong he could have been a incredibly formidable candidate but he's done none of the things you do when running for president. This tells me he doesn't want it and like's being a senator, so 2 cents is probably a bit much at this point. You can't win if you don't play!
- Kamala Harris: Matthews says sell, and I agree that 22 cents is way to high, instead put her in the middle of the pack with Cory Booker and Kirsten Gillibrand around 10 cents or so. But note that Matthews' analysis is still bad. Matthews argues that Harris, "...will face a challenge winning over Black Lives Matter activists, #AbolishICE proponents, and other voters critical of mass incarceration and police brutality." and goes on to criticize her for a bunch of other things. I think this gets the Democratic Party wrong on a number of levels. To begin with the Black Lives Matter Movement isn't really part of Democratic party politics (and they have stated that!) and itself is an composed of a whole bunch of groups with all sorts of differences that would find backing, or not backing, a candidate for president difficult for a number of reasons. Likewise #AbolishICE is a vague slogan that in my conversations seems to mean everything from "America shouldn't have immigration laws" to "Make the INS great again" so that's a loophole Harris can drive her Chevy Impala through at top speed Moreover there's a Yuge problem with party actors not being able to dismiss someone without an alternative. If you're a progressive journalist or voter who dislikes Harris you can just shout "dealbreaker!" about this or that. But if you're a party actor you kind of have to pick an alternative or be like much of the GOP in 2015-16 and remain paralyzed while disaster strikes. In other words you can say "Kamala Harris' stance on transgender rights in prison is simply unacceptable, I can't support her." And if you can't come up with who you'll back then I can barge in on your fun party, rip the mic out of your hand and shout "Which is why we are caucusing for Steve Bullock for President baby! WHOOOOO!" Is that what you want? Well no, but that's kind of the way this works.
- Bernie Sanders: I know people who read this will get annoyed, but yes sell. There's the obvious points that Sanders isn't a Democrat (problem!) and would be 81 years old in January of 2021 (also problem!). But let's just go through Matthews' points line by line:
- "He tied in Iowa last time, and there’s no regional candidate who would obviously be stronger than him there." See my Bullock post below, also the idea that "because I did good in Iowa before I'll do it again!" Isn't backed up by historical data. Once upon a time Dick Gephardt won Iowa in a shocker. Doesn't tell you what the future is.
- "He won New Hampshire in a blowout, and even against fellow New Englander Elizabeth Warren, he’s in a strong position to do the same again." This is just silly writing. New Hampshire voters are notoriously fickle and love to ask "What have you done for me lately?" of their candidates. This afterall was the state where Bill Clinton becomes "the come back kid." Where Hillary seems on the ropes and then "found her voice", where they apparently they love John McCain, and Donald Trump, and George Herbert Walker Bush, but not this son. That is to say New Hampshire voters winnow, but they all the over the map when it comes time to pick, and Dylan's theory about them being ruled by ideology or "local appeal" strikes me as nonsense.
- "It’s common for parties to choose runners-up as their nominees the next time around (as Sanders learned when he lost to Clinton)." Barack Obama, John Kerry, Al Gore, Michael Dukakis and Walter Mondale all stare at you and say "That's not how this works, that's not how any of this works."
- "He’s the genuine article in a field of imitators. If you’re a nurse in Iowa, would you rather go with someone who’s supported single-payer health care his whole life, like Sanders, or someone who signed on last year, like Booker, Gillibrand, Harris, or Warren?" This strikes me as being profoundly off base. Matthews sees a world filled with voters, caucus goers, and party actors deeply committed to ideological stances. I get that, it's a way for a "politics journalist" to think about the world, but it strikes me as missing a lot of how American party politics works. Maybe the nurse in Iowa has changed her mind, or thinks that since Bernie and Deval Patrick both support Medicare for All she'll go with Patrick because Bernie is old and Patrick is fun. Likewise maybe you've just had enough of Trump's misogyny and despite your ideological commitments you throw caution to then wind and back this woman Gillibrand because, well, what she said about Trump and women at the first debate, you can't top that.
- I'll add in that there are often claims about Bernie's powerful "organization" that he'll be able to activate for 2020. I really don't see it. Like Gary Hart, a lot of his support wasn't from people committed to his ideology or values, but rather people who disliked a party status quo. After all nobody is more Mr. Status Quo than Walter Mondale, or Ms. Status Quo that Hillary Rodham Clinton. Likewise Bernie Sanders' support in the 2016 cycle was largely about identity, that is age and race, more than anything else. Thus while there might be some core of supporters committed to Bernie personally or his ideology, it's likely much of his impressive "network" is falling apart as we speak. Especially since people who want a passionate liberal New Englander who wants to fight big business can always jump on board the USS Elizabeth Warren, who also happens to be a Democrat.
Don't get me wrong, there will be many groups and actors pushing for things like a more liberal candidate, or nominating a woman or a racial minority. The thing to remember though is that so many candidates are running you could see how coordinating around one single candidate could be a big problem for many political actors and groups. Honestly if you want to nominate a liberal woman woman you have four strong contenders so far by my count. And indeed that's a big part of how Trump was able to win the GOP endorsement! That is so many candidates were running, few dropped out, and few wanted to take him on under the theory that he would implode allowing them to gather up his supporters. So that's were you get Jeb! spending 20 million dollars to tear down Rubio in negative ads instead of Trump. And the GOP party leaders refusing to rally around Ted Cruz (probably the most viable alternative to Trump) after Iowa because they don't like him, or would rather dither. And Kasich refusing to drop out long after it's become possible to win enough delegates for him to win thus divided the anti-Trump vote for reasons.
Could something similar happen to the Dems in 2020? Probably not, but it could, and you could see O'Malley or Bullock being able to win a "bandwagon" campaign by wining Iowa and getting tons of people to jump on board, which as Seth Masket has pointed out is basically how the not very liberal Jimmy Carter was able to win four years after George McGovern.
Will this happen? Probably not. Is there a greater that 1% chance it could? Sure.