Honorable Mention: There are a lot of people considering runs for president this year (a LOT), but most of them don't warrant mention. I'm going to get into this in an article coming out tomorrow, but while there will be at least one breakout star of this bunch (it's inevitable), history teaches us that Donald Trump is the rule, not the exception. Most candidates in recent memory who won the nomination did not "come out of nowhere" but instead were relatively established before the race as serious competitors. As a result, we have a few candidates who seem to be shooting a bit too high to start the race (Julian Castro, Stacey Abrams, Andrew Gillum, anyone in the House save a certain charismatic guitar player from Texas should all try running statewide successfully before making this leap). We also have a few statewide officeholders who are too bland (Jay Inslee, Jeff Merkley, Martin O'Malley) or too conservative (John Hickenlooper, Michael Bennet, Steve Bullock) to win an election like this. Terry McAuliffe is an intriguing choice that might have made this list if it were a dozen people long, but I feel like his Clinton years have too many skeletons to survive a nationwide campaign. Howard Schultz is a billionaire who can self-fund (and unlike Trump, probably would), but it's doubtful that the Democrats will want a "liberal Donald Trump" as he will be described by the media; it's worth noting that Schultz definitely is a good orator (I've heard him speak live-he's impressive), but his labor practices running Starbucks will preclude him from making it through the primary if he ever polls high enough to be taken seriously. Angelina Jolie is interesting, though I doubt she'd actually run (I do wonder how much appetite there will be for a celebrity candidate in 2020 in general, but I'd keep an eye on her after Trump), and Eric Holder is my #11 here and almost made #10 (I'm taking a risk on #10 as I think there's only nine serious candidates right now), but I do wonder if he'd be able to make it through the primaries knowing he'd be a risky bet for the general election (few national politicians are as loathed by Republicans as Holder, and keep in mind the Democrat will have to win over some Trump supporters in order to take the electoral college). And Mike Bloomberg running is a joke, and I suspect he'll realize that about twenty seconds into the campaign when no Democrat gives him the time of day.
A Couple of Caveats: There are three names that would assuredly be on this list were they to run, so I think it's worth mentioning that they are not on this list because I don't think they will run (since all but one of the below names are purely speculative at this point, I figured I'd throw in this caveat). The first name is Michelle Obama. Obama would top this list (though I do wonder if she'd struggle to counter attack ads considering how badly it'd hurt her brand) if she were interested, but she has repeatedly made sure that people know she is not, and I take her at her word. The same can be said for Oprah Winfrey, who would also be toward the top of this list if she ran, who has been slightly coyer about running but seems to be a candidate that has no interest in making this leap. And finally, there's Hillary Clinton. You can hear the groans from certain corners of the political world, but I think she'd be around #5 on this list if she were to actually make a go of the race. We're going to be learning a lot about the Russia investigation in the next year, before votes start being cast, and repeatedly you're going to hear people claim the Democrats were cheated out of a victory in 2016, a victory that would have gone to Clinton. I think if she thought she could win she'd run in a heartbeat, but she's aware that she'd struggle in the primary; that said, Clinton has a certain devoted group of supporters who are irate she never got to be president, and would adore seeing her being the one who takes down Trump. I felt it was a mistake in 2004 for Al Gore not to run for president (I also thought it was a mistake for Clinton to miss that race as well). I don't think she'd run, but she's a serious candidate if she does despite what the Limbaughs and Hannitys would say if she entered.
The Six States That Matter: We have become accustomed in recent years to hearing about a laundry list of a dozen swing states that matter, while the rest of the country is ignored, and since the 2000 election, these states have remained relatively static. Places like Ohio, Iowa, Virginia, & Nevada have been the stars of each cycle, sucking up a lot of the time and energy of the candidates, and watching their issues come to the forefront, but that isn't how 2020 will work. While practically speaking no one is going to give up on these states (it looks bad for states that are used to having their egos stroked), the only six states that will matter in 2020 will be Pennsylvania, Wisconsin, Michigan, Arizona, Florida, and North Carolina. The first three are the three states that Hillary Clinton lost in 2016 that elected Donald Trump-were she to have won these states, all of whom had gone for the Democrats since 1992, she'd be president right now. All three states went heavily back to the Democrats in 2018, making them plum for a Democrat to win in 2020. The next three states all showed some progress for the Democrats in 2018 (Florida had razor-thin contests for governor/senator and elected Nikki Fried as Ag Commissioner, North Carolina elected a Dem Supreme Court Justice, & Arizona elected four Democratic women statewide), and are what could clearly be classified as swing states in 2020. There are other states that will be close, but if Republicans are winning Minnesota & New Hampshire, they're probably taking the White House, while if Democrats are taking Iowa or Georgia, they likely have the win in the bag. As a result I'm going to point out what kind of advantage these candidates might have in these six states below.
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| Mayor Mitch Landrieu (D-LA) |
Age in 2020: 60
Who is He?: Mayor of New Orleans since 2010
Has Held Public Office Since: 1988,without exception
President Landrieu, The Pros: While it's not something I think can be readily duplicated, Donald Trump proved in 2016 that an atypical candidate can win under the right circumstances, and though I think another celebrity candidate might be a stretch in 2020, a mayor could be well-received, especially considering that the suburbs are going to be where a candidate wins or loses, and the suburbs are used to a big-city mayor being in the news & understands the scope of their job. Landrieu is arguably the best-prepared and most interesting mayor considering a race this year, and unlike most mayors, has experience in statewide office (he was Lieutenant Governor for many years). He also has done extremely well with African-American voters in his city, and his father was a major figure in the Civil Rights movement. Plus, his sister Mary was a US Senator for 18 years, and would have connections with donors that Landrieu could tap into with ease.
President Landrieu, The Cons: "Who is Mitch Landrieu?" is likely the first sentence you just said, and you'd be correct to assume this is Landrieu's biggest deficit. While lesser-known candidates have won national primaries before (think of someone like Jimmy Carter or Michael Dukakis), they're usually governors rather than mayors. Landrieu is uniquely handicapped from his position due to the early primary schedule; while most states have a major metropolitan area that a mayor could harvest votes from in a split-race primary, Iowa, New Hampshire, and South Carolina do not, and by the time he'd get to Florida or California, Landrieu will likely be out of time to gain a foothold in the race.
States That Matter: Landrieu's long tenure as a successful mayor in a predominantly black city could be a major bonus in trying to turn out voters in Milwaukee, Detroit, and Charlotte, areas that will need to be better for the Democrats than they were in 2016.
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| Sen. Amy Klobuchar (D-MN) |
Age in 2020: 60
Who is She?: US Senator from Minnesota since 2007
Has Held Public Office Since: 1999, without exception
President Klobuchar, The Pros: America's two most popular senators come from the tiny state of Vermont, where all you have to do is lean left (and be loud about it) to keep your numbers north of 60%. What's more challenging is holding near identical numbers in a state that Hillary Clinton won by only two points. In a hyper-partisan era, Klobuchar has figured out a way to be a weirdly apolitical figure in her state, regularly winning areas of Minnesota that no other Democrat could possibly win. That sort of smart, folksy "Minnesota Nice" figure would be a really strong counter to Trump, and while there are more liberal people on this list, no one could accuse her with a straight face of being "too moderate."
President Klobuchar, The Cons: Name recognition is a factor, but I don't know that it's as big of a factor as one would assume (like it'd be for Landrieu). Instead, I wonder where her foothold is into this race other than winning Iowa. Midwestern candidates frequently hang their head on winning Iowa, only to watch their dreams get crushed because their only strategy was to win Iowa. Is Amy Klobuchar this year's Tom Harkin/Dick Gephardt, or can she pull off a feat similar to Jimmy Carter in 1976 & turn a victory there into a real campaign?
States That Matter: If she makes it to the general, Klobuchar's stance in farm country should be a big plus in Wisconsin, Pennsylvania, and Michigan.
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| Sen. Sherrod Brown (D-OH) |
Age in 2020: 68
Who is He?: US Senator from Ohio since 2007
Has Held Public Office Since: 1975, with 2 years off from 1991-93
President Brown, The Pros: Few politicians are as good at spelling out complicated economic issues to their constituents as Sherrod Brown. The longtime Ohio Democrat, one of the only remaining Democrats who can successfully win that state, is a hero of blue-collar workers (despite the fact that with his Yale background & longtime political career he hasn't resembled them in decades), and would be a fascinating counter to Donald Trump as Brown is so genuine on the stump and would be going for the same voters that Trump convinced to abandon Democrats two years ago. As one of the rare Democrats with a liberal enough background to succeed in a primary (from a red state), no one should dismiss Brown out-of-hand.
President Brown, The Cons: You'd think my problem here would be that Brown, a straight white man in a primary field that will be clamoring for diversity, would struggle to gain a foothold, but I don't think that's the case. Brown, after all, will do well with Labor, which should help in Iowa and Nevada. My problem with Brown is that his Senate seat will go red if he wins the presidency, and I think that will be a problem that'll be easy for his primary opponents to communicate to voters. "Sherrod Brown's great, but we need him in the Senate" might not matter if he were the only candidate who could actually beat Trump, but Democrats don't think that right now and will probably be choosy, especially after Merrick Garland (I suspect pushing for a Democratic Senate to be a bigger deal than usual in 2020 due to RBG's near certain retirement/celebrity status). As a result, I think Brown might have sunk his chances by not getting Richard Cordray elected last November.
States That Matter: Pennsylvania & Michigan have very similar voting profiles to Ohio, except they're much bluer. Brown's ability to speak to said voters would surely be a plus for him. Plus, he theoretically could make Ohio more competitive, nothing to sneeze at if the national polls show it closer than I'm anticipating right now.
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| Sen. Bernie Sanders (I-VT) |
Age in 2020: 79
Who is He?: US Senator from Vermont since 2007
Has Held Public Office Since: 1981, with 2 years off from 1989-91
President Sanders, The Pros: Sanders goes into this election with an army of supporters ready for his announcement. The Vermont senator did surprisingly well in 2016, and history has been kind to runners-up when they run four years later for the nomination (Ronald Reagan, Hillary Clinton, Mitt Romney)-could Sanders turn a splintered field to his advantage, knowing that he'll start the race with a bigger piece of the pie than most other Democrats on this list?
President Sanders, The Cons: For every Bernie Bro, there's someone who is "anybody but Bernie." Sanders age makes him more vulnerable than most (nearly 80-years-old, he's more susceptible to health-related rumors), but I think his biggest problem is that there is a large part of the Democratic Party who blames him for not dropping out sooner in 2016, splintering the party and denying Hillary Clinton a unified front headed into November. This might not be entirely fair to Sanders, who did obviously campaign for Clinton, but it's there and what's keeping me from thinking of him as a frontrunner, when in most other situations he'd have to be considered one.
States That Matter: Sanders would need to appeal to working-class white voters, which seems like a Wisconsin and Pennsylvania situation. I will say that of all of the candidates on this list, he arguably has the least obvious stronghold in the six states I profiled, due mostly to his proven (poor) track record with winning Latino and African-American candidates in the 2016 primaries.
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| Sen. Kirsten Gillibrand (D-NY) |
Age in 2020: 54
Who is She?: US Senator from New York since 2009
Has Held Public Office Since: 2007, with no exceptions
President Gillibrand, The Pros: Gillibrand is smart, great-on-the-stump, and coming from New York, can raise boatloads of money in relatively short order in a way that few others on this list would be able to do. She's also got a unique ability to appeal to suburban voters-she's from New York, but represented upstate New York, so while she has had to rely in large part on New York City to win in the Senate for the past decade, she also does extremely well across the state and has an opportunity to make a play for suburban moms in a way that no other candidate is able to do. Considering the strong shift among, in particular, college-educated white women to the Democrats in the past couple of years, this could be a huge coup for her in the generals, and if these constituents are passionate about turning out, in the primaries as well.
President Gillibrand, The Cons: Gillibrand has two major debits against her, one completely unfair and one relatively valid. Proving that sexism is unfortunately a bipartisan issue, Gillibrand is frequently blamed in some circles for the resignation of Al Franken because she was one of the more vocal senators in calling for his resignation (despite the fact that evidence and multiple women point to clear inappropriateness on Franken's part). This could hurt her with primary voters who are loyal to Franken despite it making them massive hypocrites. The second, more valid reason that she could be vulnerable is Wall Street. Representing New York, Gillibrand is cozier to business and financial interests than your average Democrat would be, and this would be a very easy weapon for the likes of O'Rourke, Sanders, & Warren to levy against her in the primary as these institutions are not popular with rank-and-file voters in an era where Democrats are increasingly left-leaning on fiscal issues. Gillibrand's ability to manage these attacks will define her ability to win the primary.
States That Matter: I suspect that Gillibrand would be one of the better general election candidates if she made it there, and might be able to sweep all six of these seats because of her ability to appeal to swing voters in the suburbs. Florida, Pennsylvania, and Michigan seem toward the top of the list, but if I were Donald Trump, she'd be the candidate I'd most worry about facing in 2020.
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| Sen. Cory Booker (D-NJ) |
Age in 2020: 51
Who is He?: US Senator from New Jersey since 2013
Has Held Public Office Since: 1998, with 4 years off from 2002-06
President Booker, The Pros: Frequently it is commented upon that a president is succeeded by his polar opposite. Four years after Richard Nixon, the consummate DC insider, was elected, he was succeeded by a humble peanut farmer from Plains, who was then succeeded by a folksy movie star then by a blue-blood White House lifer to a young, slick-talking philanderer to a bumbling family man to a black Harvard law professor who started from nothing to a trust fund racist who can't handle even the mildest of slights. This isn't just a fun parlor game-it shows that America tries to correct the thing they hated the most about their last president. As a result of continuing this trend, you would struggle to find a candidate on this list better suited to counter the cruelty, nastiness, and racism of the Trump administration than Booker, who comes across almost comically nice (he's literally tweeted me before to say "All the best" and wish me a nice day) and is meticulously woke. Booker is going to play extremely well in living rooms across America (he'll nail the talk show circuit), and don't underestimate his ability to inspire people by basically being the anti-Trump (contrary to popular opinion, a challenger for the White House really only needs to be the "anti-incumbent" to actually win-they don't really need to have much else going for their campaign).
President Booker, The Cons: One of the things you can expect from the Democratic Primary is that it will be a lot kinder (at least on the surface) than a Republican contest would be. There's an old adage that "Democrats fall in love, Republicans fall in line," that feels particularly apt here, so you don't want to tear down each other on the campaign trail, and most attacks will be relatively substantive. This is going to be a problem for Booker, because he's one of the few candidates on this list who strikes out in a major way on a key Democratic issue: school choice. While Booker (smartly) voted against confirmation of Betsy DeVos, he did work with her in the past and has been supportive of school choice in a way that most other candidates on this list haven't. Considering it'll be difficult to go against Booker on style or character, most of his opponents will likely define him as aligned with DeVos and Republicans on school choice, which would be a critical hit in a field where Democratic voters are relatively undecided & looking for justifications to winnow their field.
States That Matter: It's hard to tell if historically high black voter turnout in 2008 and 2012 can be duplicated in the same way for the second black president, but if so Booker would be able to have an advantage in places like Charlotte or Detroit. His successful tenure as Mayor of Newark (and as a senator from a very urban state) also should help him with larger cities.
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| Sen. Elizabeth Warren (D-MA) |
Age in 2020: 71
Who is She?: US Senator from Massachusetts since 2013
Has Held Public Office Since: 2013, with no exceptions
President Warren, The Pros: I don't quite subscribe to those people who think that Warren would have beaten Hillary Clinton in 2016 had she run. I think the only person who genuinely would have bested Clinton in the primaries was Biden, and he would have been an underdog; lest we forget, Bernie Sanders outperformed expectations-he didn't actually get close to winning. That said, Warren has amassed a huge following and feels like she can get pretty much every one of the Bernie Sanders voters who would actually vote for a woman (and aren't just men who say they would vote for a woman, but when a literal one comes up they go running), and no other Democrat has more defined the policy priorities of the left during the Trump years than Warren (Alexandria Ocasio-Cortez may be the future of the party, but her message feels remarkably similar to the present of the party, Elizabeth Warren). Give her a stump speech, and she'll get liberals in Iowa and New Hampshire very excited.
President Warren, The Cons: Warren is not a natural politician. That won't hold her back completely (neither was George HW Bush or Mitt Romney, and they both won their nominations), but she's a bit stiff and comes across as a Harvard law professor, which feels accurate because she is one. She also royally bungled the ancestry question by saying "I'm a little bit Native American" (in so many words), and feels a lot like Hillary Clinton or Al Gore in the sense that she would make a fine president...but she could just never win the office. Combined with Democrats being leery about betting on another Massachusetts liberal after Mike Dukakis and John Kerry, and you see why Warren just misses out on the Top 3 even if her crowd sizes are huge and her fanbase has some depth.
States That Matter: Warren's message will be one of economic populism. That should play better in the Midwest, states like Michigan and Wisconsin, than it would someplace like Arizona. Warren has also been bold in her conversations about criminal justice reform, which may make her stronger amongst black voters than Bernie Sanders was (giving her openings in places like North Carolina or Florida).
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| Rep. Beto O'Rourke (D-TX) |
Age in 2020: 48
Who is He?: US Congressman from Texas since 2013
Has Held Public Since: 2005, with two exceptions (2011-13, 2019-Present)
President O'Rourke, The Pros: While it's occasionally eye-rolly that the Pod Saves America guys are salivating over O'Rourke (I don't listen to them because they seem to fall in love with every straight guy they can find), there's no denying that Beto O'Rourke has a gift that few politicians are able to achieve. Arguably the most engaging speaker on this list, he'll stand out from the rest of the Democrats on the podium in a similar way to Barack Obama and Donald Trump before him. It's not entirely clear if he'll actually run, but the fact that he got extraordinarily close to Ted Cruz in Texas of all places shows some serious skills, and there's an excitement around his candidacy that I don't remember seeing since a young Illinois senator a decade ago.
President O'Rourke, The Cons: For starters, he's a congressman who just lost a Senate race, and people don't lose elections and then win the White House without getting a victory in between. History, yes, has a couple of examples (Abraham Lincoln lost a Senate race in 1858 but then won in 1860, while Richard Nixon lost a governor's race in 1962 & then won the White House in 1968), but Nixon had been a national figure for decades when he won in 1968, having served eight years as VP, and Lincoln was 160 years ago (and politicians have long gotten in trouble comparing themselves to Lincoln). O'Rourke is not an old man, and may well want to try for the Senate seat in Texas this year instead, as he'd have a clear path to the nomination, and considering what he did in 2018, may be able to use presidential year turnout into a win there (and then have a much stronger position to run for POTUS in 2024 or 2028). But I have to admit-I was a lot more skeptical of this in October when it looked like he'd lose by ten points than I was when he did better than people like Claire McCaskill or Joe Donnelly did-O'Rourke is the real deal, and he may never have the kind of momentum he has right now again. If he has designs on the White House, he may be looking at his best shot.
States That Matter: O'Rourke's strong support among Latino voters (exit polls show him clobbering Cruz with Latino voters) puts him in a unique position to make a serious play for Arizona and Florida, two key swing states you're not seeing a lot of on this list. Honestly, like Gillibrand, I think he might be one of the better options on this list if he were the nominee, provided he could get past the experience card with voters.
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| Vice President Joe Biden (D-DE) |
Age in 2020: 78
Who is He?: Vice President of the United States from 2009-17
Has Held Public Office Since: 1970, though not since 2017
President Biden, The Pros: Everyone likes Joe. Biden has some of the best approval ratings in the country (you have to go to apolitical figures like Michelle Obama to get similar numbers), and shows up at the top of almost every poll you see of the D race. He's the most experienced candidate, he does well with pretty much every Democratic base demographic, and honestly he clearly, really, wants this and knows he'll never have another shot at being the president (he ran twice, and likely would have run two years ago had his son not died). In a wide open field, he's the only person who could generally be considered the frontrunner, and that helps more then you'd think (it's hard to argue he's in a worse position that Bob Dole in 1996 or George W. Bush in 2000 right now). If 5-6 people on this list start splintering the vote, he's probably the nominee.
President Biden, The Cons: There's a few things. The most obvious is Biden's age and gender. In a party that is increasingly looking for younger, more diverse candidates, Biden is a nearly 80-year-old straight white man who has been in politics since Alexandria Ocasio-Cortez's mother was only seven. It's hard to fathom that Biden would be able to win over vast swaths of primary voters who were hungry for a change in 2018, particularly considering how weak Trump's approval ratings are (if they were stronger, he might be able to sneak in as the "only person who can beat him," but that argument doesn't hold water even if he might be the "strongest" person who can beat him at this juncture). His age also matters for practical purposes (the media will be watching his health and public statements with more scrutiny than they will Beto O'Rourke's), and he's considerably more moderate than many of these candidates-don't expect someone like Elizabeth Warren to avoid punches even against the venerable Biden. Plus, he's going to have to find a way to get around Anita Hill without coming across as too defensive, or he could lose female voters fast.
States That Matter: Perhaps you've heard this before, but Joe Biden is from Scranton. Honestly, between his PA roots and what Obama did for the automotive industry, no candidate on this list is better suited to picking up the three states that matter most (MI, WI, and PA) than Biden. While I think Gillibrand or O'Rourke might be better at sweeping all six, if you are just focusing on getting to 270, a healthy Joe Biden is your best bet. Also, because I love trivia-the Silent Generation is the only generation that has been able to legally become president and not done it yet-Joe Biden is almost certainly their last shot at ending that statistic (unless somehow Nancy Pelosi does it during an impeachment hearing).
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Age in 2020: 56
Who is She?: US Senator from California since 2017
Has Held Public Office Since: 2004, with no exceptions
President Harris, The Pros: There's a lot of reasons I'm putting Kamala Harris at #1 on this list, but one of the biggest is black women. You can't become president without winning your primary, and increasingly you cannot win the Democratic nomination without strong support from black women. Barack Obama proved this by winning over black women (against Hillary Clinton), and then black women proved to be the kryptonite to Bernie Sanders hopes in 2016. Harris seems best-poised to win over black women not only because she's a woman of color herself, but because she is really good at pointing out the new unique struggles that women of color experience in their day-to-day lives. She's well-liked among female voters in general, and has the right level of experience on a national level (she's in her first-term, but is a sitting senator so it's hard to paint her as either inexperienced or a career politician), & is better than most candidates at this list at going after Trump. Harris's likely support from women of color is enough for me to think she's the prohibitive frontrunner before we see any actual candidates on the trail.
President Harris, The Cons: There are three things that Harris should be apprehensive of at this point. The first, and this cannot be underscored enough: she is not the female Obama, which is something she was frequently billed as by a lazy press prior to her winning the Senate. In 2012, she appeared at the DNC, and unlike Obama in 2004...no one really cared. It was an okay speech that made some raise their eyebrows over whether she was the future president she was being billed as. There are things that Harris appears better at than Obama (she seems more attuned to DC than he ever was, which could make actual legislating that much easier if elected), but she's not as noteworthy of a speaker and feels more like a really good DA than a really good politician. Secondly, relying on black women is a good, but not fool-proof strategy for a Democratic primary. John Edwards did marvelously well with black women in 2004, but ended up losing because John Kerry was stronger among black men. Watch Harris's numbers with black men as she continues her campaign, as that would be an opening for a Biden or O'Rourke if she cannot get similar levels of support. And finally, it is always risky to bet on only one of the early states delivering you a pass to the rest of the contest, and Kamala Harris will need a victory in South Carolina if she has any hope of winning the White House. If she cannot take the victory at that point, someone like Warren, Biden, or O'Rourke could take out their strongest opponent early as she'll have gone too long without a win and will be just a candidate for the veepstakes. Still, I think Harris has to be considered the nominal frontrunner at this point in the race.
States That Matter: As I mentioned, if we could see similar numbers to those enjoyed by Barack Obama in 2008 and 2012 amongst the African-American communities, places like Florida, Michigan, and North Carolina would be strong bets for Harris. I also think she speaks to Arizona voters in a way that other candidates don't on this list save O'Rourke.
There you have it. In 2016 I did this and one of those candidates appeared prophetic (Clinton obviously won her nomination), the other foolhardy (Trump wasn't even on the list, and my initial choice of Jeb Bush looks laughable in hindsight considering his performance). We shall find out a year from now what camp these predictions will fall under, but stick around as the race for the White House will be followed closely on this blog.
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