Now, in this regard, don't get used to me talking about 2020, because I abhor discussing races this far out as a general rule. For starters, I think that the newly-elected candidates should be given a chance to actually govern. The media's focus on the next election rather than holding our current officeholders accountable has long been a pet peeve of mine, and even if I didn't vote for the incumbent president, that doesn't mean that I'm a complete hypocrite on this, even if it might soothe my wounds to start fantasizing about the day when he might leave office.
Secondly, predicting presidential races nearly four years out is an absurd task. Occasionally you can make sense of the nominees; people like Bob Dole, John McCain, Mitt Romney, and Hillary Clinton, if you'd told me six months after the previous election that they were the next cycle's nominees, I'd have nodded and said "makes sense." But just as frequently people like Jimmy Carter, Bill Clinton, Barack Obama, and Donald Trump come along and I'd have laughed you into the next room for predicting such a thing. Politics is sometimes an industry that rewards the most-likely-successor and occasionally she gives in to a completely new name.
Finally, even if we want to presume on the nominees, predicting the presidential race three years from now is impossible. Democrats may be salivating at Trump's dour approval numbers, but approval numbers this early in a presidency mean nothing (unless you're Jon Ossoff, in which case you're probably feeling appropriately cocky right now). Don't believe me? Just ask Bill Clinton and Ronald Reagan, who had abysmal moments in their first terms that surely would have meant them losing reelection...except of course they won in landslides. Conversely, Republicans shouldn't be particularly sure here either-George HW Bush and Jimmy Carter both seemed like very likely winners for second terms mostly because of a thin bench from the opposition, only to have to endure that most odious of presidential retributions: a reelection loss.
So the focus here is not on who will win or even who will run, but instead on 21 names in the Democratic Party that I think should run, shouldn't run, or where I'm undecided. Most of these names are politicians being floated for higher office, some are just ones I wanted to insert into the conversation preemptively. Feel free to chime in in the comments with names I missed or who you're hoping joins the conversation.
(Note: I'm listing each group of seven in alphabetical order-I might call out my favorite candidates, but I'm not ranking since, as I've said, it's way too early for such things)
(Second Note: You'll notice I lean a little heavier into electability than you normally would on a personal list like this. This is for two reasons: 1) as a rule I agree with most of these people on most issues, and I think that conversations that start with "not a true liberal" in this hyper-partisan age are unproductive and 2) successful presidential challengers usually win based on being deeply electable-Jimmy Carter and Bill Clinton, for example, were moderate Southerners who were very likable when they first ran. As a result, I'm going to be putting a little bit more emphasis on public persona than if I were to just, say, "pick" the president rather than assume that he or she has to win two very difficult elections to get to that position)
Candidates I Hope Will Run
Age in 2020: 54
Why I Hope She Runs: On the list of candidates that I'm hoping will run, you're going to see a lot of names of people who probably won't make a go of it. Much like 2004 where I ended up sitting for Wesley Clark in the primary, I anticipate 2020 being a year where I'm more voting "against someone" than voting "for someone" in the general as our bench isn't that exciting. The lone exception there is Gillibrand, who has proven to be a strong leader for women's issues, the environment, and has started to emerge as a foreign policy voice in the Senate. Arguably she's Hillary Clinton without all of the baggage or stigma, and has been positioning herself as the perfect foil against Trump.
What Holds Her Back: One of the bigger issues that Democrats need to address between now and 2020 is that they will need to either win back the Obama Midwestern/Great Lakes states (principally Michigan, Pennsylvania, and Wisconsin) or take a crack at FL/NC/AZ, which have become friendlier for Democrats but not reliably so. A New York liberal senator isn't exactly a recipe to solve either of those two problems.
Sen. Maggie Hassan (NH)
Age in 2020: 62
Why I Hope She Runs: Hassan barely won her Senate election in 2016, but she did win and as a result she's one of the only women in history to have held a Senate seat and been governor. That dual experience could come in handy if the Democrats are able to run on a revolving slate of staffers in the Trump White House (so far, there's no indication that that couldn't happen). Hassan also has been pretty impressive in Senate hearings so far-frequently finding her way into headlines, and finding quick ways to differentiate herself from the Trump administration while still maintaining an aura of moderation in a purple state. That sort of balancing act will be handy in a presidential primary.
What Holds Her Back: Does she want this? I honestly think that if I were running a theoretical Joe Biden 2016 presidential race that I would have gone with Hassan over an Elizabeth Warren as a running mate in part because she feels like one of the under-tapped talents in the Democratic Party. But in an already crowded field, can she differentiate herself quickly enough?
Sen. Amy Klobuchar (MN)
Age in 2020: 60
Why I Hope She Runs: Admittedly Klobuchar is on this list in part because of home state pride, but it has to be said that she's an attractive candidate on paper (another candidate who would have been better on a Biden ticket in 2016 than Warren). She's turned what could be a tossup seat into an easy victory for the Democrats, as she's wildly popular in the Gopher State. She's a former prosecutor, so she's sharp in a debate but comes across as very personable (it's easy to see her playing well in Iowa or South Carolina). And she's quirkier than you'd expect from a Midwestern senator, which may play well as Democrats are accused of being out-of-step with the average voter (arguably Trump's most successful line-of-attack in 2016).
What Holds Her Back: Klobuchar has had over a decade to distinguish herself on the national stage, but has never really taken that leap from Senate workhorse to Senate show horse, the latter of which she'll need to be in a primary that could be littered with big names like Bernie Sanders, Elizabeth Warren, and potentially even her fellow Minnesotan Al Franken. If she can't find a way to become part of the noise headed into at least the 2018 elections, it's hard to see where the room is at the table for her candidacy.
Age in 2020: 67
Why I Hope She Runs: If you didn't see McCaskill coming on this list, well, welcome to my blog (I'm an enormous fan). McCaskill may be one of the older names on this list, but she'll be younger than Trump or Hillary was this year when 2020 rolls around, and she's arguably one of the ballsiest and most tenacious members of the Democratc Party (again-I would have skipped Warren entirely if I ran a Biden 2016 campaign and just had Hassan, Klobuchar, and McCaskill on my list-I'll engage in the comments if you'd like to talk about which would have been the better running mate). McCaskill has won a tough battlefield a couple times now in Missouri, so she'd be able to translate those skills to places like Michigan and Pennsylvania, and I suspect that she's at least thinking about this with surprisingly liberal votes on the Gorsuch nomination.
What Holds Her Back: For starters, she's nowhere close to a sure thing to win in 2018, and she has to win reelection to be a contender in 2020 (just ask George Allen and Roy Barnes what putting the horse before the cart got them in presidential politics). Secondly, it's hard to picture the Democratic Party going with someone as moderate as McCaskill, even if it might be in their best interests. If Hillary Clinton was considered too moderate in 2016, I cannot fathom McCaskill emerging unscathed four years later. Still, Donald Trump broke a number of "you're not allowed to say that" rules in the GOP primary in 2016-McCaskill could do the same in 2020.
Sen. Jeff Merkley (OR)
Age in 2020: 64
Why I Hope He Runs: If I'm going to get a true, died-in-the-wool liberal, I want one that will be able to resonate with younger voters and actually get them to come out, and one who seems to have at least a grasp on bipartisanship because one-party rule until they lose is a terrible system. Merkley fits that bill arguably better than anyone else if I'm forced to pick a very liberal senator, and he has been making rather impressive waves in the media (that Supreme Court filibuster surely didn't hurt), as well as reaching out on a more national stage. He also has won a difficult election before (beating an incumbent in 2008), something few blue-state Democrats can boast.
What Holds Him Back: It's hard to see how Jeff Merkley enters the national stage in a way that Bernie Sanders or Elizabeth Warren don't already. Admittedly, if both pass on the White House, I could see this being his opening, but otherwise-is there room for a third hyper-liberal senator in this race? How does he distinguish himself even if he's ultimately the most talented politician of the trio?
Sen. Chris Murphy (CT)
Age in 2020: 47
Why I Hope He Runs: Murphy has fast-emerged as someone to watch in the Democratic Party. His views on gun control proved that he can make a national moment for himself, and his continual push on liberal issues makes me think that he wants to jump onto a national stage, though perhaps not as soon as 2020 given his relatively young age and safe seat. Still, he'd draw a stark contrast to a 74-year-old president (the same contrast many expected between Hillary Clinton and Marco Rubio in 2016), and even though he's from a blue state, he's not a stranger to winning tough elections (he had to take out a long time incumbent to get into Congress).
What Holds Him Back: I cannot stress this enough, but Democrats have had their hearts broken by New England liberals one too many times at this point, and even the ones who seem different end up failing us in the end. Murphy will have multiple other chances to run if he so chooses-would he really want to take an on incumbent?
Rep. Adam Schiff (CA)
Age in 2020: 60
Why I Hope He Runs: I'm not wild about members of the House running for POTUS, but Schiff has impressed me enough in recent weeks that I would entertain this possibility. He's got a pretty interesting perch to challenge Trump by proxy for in the next two years on House Intelligence (and the Devin Nunes fiasco only helped Schiff in terms of making him appear bipartisan), and as a result he's one of the few Democrats who won't have to fight to be in the news or for partisans to rally to his side. Plus, he's very smart and can shore up a weak point Democrats frequently have in presidential elections-military/foreign affairs.
What Holds Him Back: Partially it's the House thing, but more so it's the fact that he won't be able to trumpet any of his views on liberal hot topics like student loans, climate change, and criminal justice-he'll just be the Trump watchdog, and Republicans may have a field day if the House Intelligence committee chair goes onto the top of the national ticket. Still, though, if I were to pick my true dream ticket for 2020, it'd probably be McCaskill/Schiff at this point.
Candidates I Hope Won't Run
Age in 2020: 82
Why He Might Run: Because Jerry Brown always runs for president. Seriously-is there any other living credible candidate (he's been governor of the most populous state in the country for almost sixteen years!) who has run for president as often as Brown who hasn't become the nominee? Brown has never given up on his dream, and while he surprisingly sat out 2016 (I was sure he'd make a play against his nemesis the Clintons), he's still chatting away about running in 2020.
Why I Don't Want Him: Jerry Brown is too old to be president. At 82, I might buy him if he was the incumbent, but making a first-round pass just doesn't fly here. Brown arguably has the voting record that could get him elected, but his age combined with his abysmal track record at making plays for federal office (three failed presidential races, two Senate losses) makes me think that this was never in the cards for the perpetual governor.
Sec. Julian Castro (TX)
Age in 2020: 46
Why He Might Run: Castro honestly has nothing else to do but run for POTUS at this point. As a former mayor who has no obvious paths to higher office (it'd take a miracle for a Democrat to win a Senate or gubernatorial campaign in Texas), he was really counting on Clinton winning to either be her running mate or get a promotion in her cabinet, thus helping to keep him on the national stage. Since he doesn't have those things, and since he represents a burgeoning voter bloc in the Democratic Party (no other major Latino candidate seems destined to run in 2020), he might see an opening.
Why I Don't Want Him: Secretary of HUD and Mayor of San Antonio are not good enough qualifiers to be able to take on Donald Trump in 2020-I want someone with statewide experience, preferably a senator, who knows how grueling the national spotlight can be. As someone who sees that Castro has a lot of potential it troubles me that he doesn't have an obvious way up (I feel the same way about Jason Kander in Missouri), but putting him on the national ticket is too big of a risk.
Gov. Andrew Cuomo (NY)
Age in 2020: 62
Why He Might Run: While his father was the perpetual Hamlet on the Hudson, his son has always felt more likely to make a play for national office. Andrew Cuomo is a very powerful figure in a high profile state, and as Donald Trump's governor, will be able to draw POTUS into public arguments more easily than your average politician. Additionally, he'll have an enormous donor base to tap into, and it's likely he'll still be the incumbent in 2020, so raising money in NYC may be tougher than it seems for anyone who isn't Cuomo.
Why I Don't Want Him: I know I said up-top that I would largely disregard policy. Well, that can't quite stop me in some cases, particularly with Cuomo, whose viewpoints on too many issues I find divergent from my own. More importantly, I think his sort of monied, Wall Street-style approach to politics is going to alienate the same left-leaning crowd who wouldn't go for Clinton in 2020. If you think Jill Stein can gain with HRC, imagine someone as entrenched on the subject as Cuomo.
Age in 2020: 69
Why He Might Run: I actually get this, and of the seven names listed here this is perhaps the only one I could see me changing my mind on in a primary. Franken has fast emerged as a national hero for some parts of the left, using his bully pulpit to take on the likes of Jeff Sessions and unabashedly go after Donald Trump. That's going to endear him to the primary crowd who is looking for some sort of hubris against the president. Franken also has the comedic and improv skills to go toe-to-toe with Trump in a debate, and as a two-term senator you can't really argue that he doesn't have the qualifications even if he also comes from the "celebrity" camp.
Why I Don't Want Him: I think one of the things that the Democratic Party will need to deal with in 2020, provided that the political environment still somewhat resembles the current atmosphere, is that they have a burning desire to see Trump humiliated. No politician will be able to make Trump look like a moron faster than Harvard-educated, SNL-trained Al Franken, but that's not what I want. I'm looking for a candidate that can beat Trump, not humiliate him. I'm not convinced that another candidate that appeals to the backrooms of the DNC but not necessarily the heartland is the way to go here.
Sen. Bernie Sanders (VT)
Age in 2020: 79
Why He Might Run: It's often said the best way to predict if someone will run for president is if they've already run. Sanders, at this point, has already run and tasted what second place is like. It's hard to imagine him passing on millions of fans across the country, particularly when he would arguably start the 2020 election in a leading position. While his age is a deterrent, in terms of actually running I'd bet solid money that Sanders would make a play for the White House once again in 2020.
Why I Don't Want Him: Sanders is too old and too liberal to win the White House, and it's doubtful that Donald Trump is the best Republican candidate to go against him (Sanders was always going to be a better Democratic foil to someone like Ted Cruz than a Republican who can lean into populism like Trump). Sanders also proved to be a bitterly bad team player in 2020, and I don't need that in the primary in 2020. Having Sanders in the race will mean that there's the risk of the "Bernie Bros" staying home again, something the Democrats (clearly) cannot afford.
Sen. Elizabeth Warren (MA)
Age in 2020: 71
Why She Might Run: In hindsight (always a 20/20 proposition), Warren was the candidate the Democratic Party wanted in 2016, but she wasn't ready or brave enough to run. A more palatable politician than Sanders, her stances on the issues make her hard to topple in terms of straight liberal politics, and she's more than willing to put herself out there to attack Donald Trump. Warren may have wanted to wait, assuming Clinton was invincible, but in 2020 she starts as arguably the frontrunner for the nomination (if I were a gambler, I'd bet on her for the nomination), and it's very, very, very hard for a politician of her level to turn down a chance at the ultimate promotion.
Why I Don't Want Her: For all of her attributes (she's a smart woman), she is not a great retail politician. She was helped in 2012 by a national wave and Scott Brown not being the finest politician either, but it says something to me that her approval ratings aren't great even in ocean-blue Massachusetts. Plus, she's not great on the stump and she's not a great team player (I want a presidential nominee in 2020 who's willing to take the baton up-and-down-the-ballot). It's hard to imagine her beating Trump, quite frankly, a task I can envision multiple other people on this list pulling off.
Age in 2020: 66
Why She Might Run: Because if Trump can do it, why can't other billionaires? Winfrey sits here in part as a proxy for other names like Bob Iger, Howard Schultz, Mark Cuban, and Mark Zuckerberg, all of whom have made rumblings about running for POTUS in 2020. It's not the craziest idea-if Trump's election issued the dawn of the "are you not entertained?" portion of American politics, it may make political sense to fight fire with fire, bringing out another billionaire to test his endurance. And it's hard to argue that Winfrey doesn't come with a legion of devoted fans.
Why I Don't Want Her: Because I don't want the presidency to become a reality show. I don't like the lack of experience Donald Trump brings to the White House-it is arguably the thing that troubles me the most about his position. I'm not a hypocrite on this front-I don't want someone who can simply buy their way to the Oval Office to be able to do so. I have a lot of respect for Winfrey as a person and entertainer, but I don't trust her with the nuclear codes or handling international affairs.
Candidates I'm Undecided Upon
Vice President Joe Biden (DE)
Age in 2020: 77
Why I Hope He Runs: Because I love Joe Biden. Biden has been arguably my favorite politician since I was a teenager, and that will never change. His "Uncle Joe" persona may have been a major miss for the Democrats in 2016 (it's hard to know if he would have beaten Trump, but it's likely that he would have been our best candidate), and he clearly wants this. I said up-top that Jerry Brown is the man who has pursued the White House more than any other living non-nominee, but I might need to amend that statement to include Joe Biden. His age won't be a huge factor if he's healthy considering he's not that much older than Trump.
Why I Don't Want Him: Biden's skills on the stump are legendary, but occasionally infamous, and while you might think that gaffes aren't as significant in a post-Trump era, they still matter and will still be used against him (just look at the "basket of deplorables" line on Clinton). Plus, combining his age and the Democratic Party's desperate need to go into a younger direction, I just don't think Biden should be the nominee unless it's clear he's the only one who will help us to win.
Age in 2020: 51
Why I Hope He Runs: It's hard not to like the handsome, social media-adapt, life-saving junior senator from the Garden State, and don't think that Democrats haven't noticed. Booker has graduated to a very prominent role in the party, getting a primetime spot in 2016 without having run for president (or being related to someone who did), something only Elizabeth Warren can also boast. Booker is affable and deflects criticism extremely well. Personality-wise, it's hard to see two such different public figures as Trump and Booker.
Why I Don't Want Him: Booker's politics are a little murky on issues that Democrats need to hold their ground on (specifically education), and his personality could come across as phony or cloying much more easily than most of the other people on this list. He clearly wants this (I'd guarantee he's running in 2020), but I'm worried he might be the Democratic Marco Rubio-he doesn't seem to have as grounded of principles as the likes of Warren or Biden.
Sen. Sherrod Brown (OH)
Age in 2020: 67
Why I Hope He Runs: Occasionally the solution to your problem is to go to the most obvious source-if you're having trouble winning in Great Lakes states, pick someone who already has done that and run him. Though there are other Democrats that come to mind, the only one who seems destined to run for POTUS is Brown, who has managed to be both a hyper-liberal and represent a light red state. That's a difficult balancing act, and Brown has proven several times to be a fighter so tough elections are not new territory for him. He's already getting buzz from the grassroots-could he be a more electable Bernie?
Why I Don't Want Him: I'm not entirely convinced that geography is what will help us win Wisconsin and Pennsylvania back-I think it's an attitude toward the voter. As a result, I believe that Brown is perhaps too liberal to win a general election (I think, quite frankly, that the best candidate for the Democrats is a social liberal/economic technocrat, but that person doesn't really exist), and may just be a good-on-paper candidate. Plus, like McCaskill, he has to clear 2018 first.
Sec. Hillary Clinton (NY)
Age in 2020: 73
Why I Hope She Runs: Because she won the popular vote in 2016, and because I've wanted Hillary Clinton be president since I was old enough to read. And because half of you reading had your heads explode with joy when you saw her name.
Why I Don't Want Her: Because in 2016 she managed to lose to the most controversial candidate for POTUS in at least a century-she's had her shot. And because half of you reading wanted to vomit when I suggested her as a candidate.
Age in 2020: 63
Why I Hope He Runs: Cooper is an interesting candidate as he's one of the few age-appropriate Southerners left in the Democratic Party, and as a result might be able to translate well to places like Florida, Georgia, or North Carolina as the Democrats lose some of their strength in typical swing states like Iowa and Ohio. Cooper will have plenty of chances to run in with the unpopular state legislature in the state, and is one of the few governors nationally who give off indications that they could run nationally AND be good candidates.
Why I Don't Want Him: It's very early in his tenure, and if his focus is more on state issues his profile may end up too moderate to ever survive a primary (or even be approved for the second spot on a ticket). I think Cooper is a name that should probably be bandied about more, though, even if he ultimately decides against running as Democrats will need to use his mold to start winning back purple states.
Sen. Kamala Harris (CA)
Age in 2020: 56
Why I Hope She Runs: There aren't a lot of superstars in the party if you've been able to parcel that out from this list. Harris is one of the few emerging ones, after taking a pretty quick trip to the Senate in 2016. It's still early, but it's clear that she's starting to cut a progressive mold more in the line of Kirsten Gillibrand than Elizabeth Warren, and is working her celebrity well to get traction on issues but not losing sight of her being a freshman senator. That shows political moxie, and as a result she may be the most impressive member of the recent freshman class.
Why I Don't Want Her: It's arguably too soon for her to run, and it's not clear that a California lawyer is going to be who the general electorate wants to rally behind. More importantly, though, is that Harris is not a good retail politicker-her speeches are frequently stiff and she's been somewhat lucky in getting opponents who can't compete on her level in a blue state. I want to see her actually best a major player like Mitch McConnell or Donald Trump before I back her for this office.
Gov. John Hickenlooper (CO)
Age in 2020: 68
Why I Hope He Runs: Governors from swing states are in short supply for Democrats, but Hickenlooper, twice elected in Colorado, is the exception. A businessman who seems to be more beloved inside the Beltway than well-known outside of it, I continually see him talked up as a candidate with potential by political insiders. Though I haven't seen that skill, part of me wonders if he just hasn't had the opportunity to show it. There's room for a left-of-middle pragmatist governor in this race (I don't see one running).
Why I Don't Want Him: Hickenlooper has gone to the right on some issues that could haunt him, particularly when it didn't feel like he had to go there. Additionally, his electoral margins were underwhelming (even if he did indeed win), and my gut says that he'd make a better running mate for an up-and-comer like Harris or Booker than someone who makes sense on the top of the ticket.
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