Dozens of Democrats are eyeing a run against President Trump, whom they see as particularly vulnerable. Trump has sounded off on some of them, occasionally with praise, and often with mockery.
I asked my colleagues at the Washington Examiner’s commentary page, “If you were Donald Trump, which candidate would you most like to face? Which would you least like to face?”
Here are their answers, with mine at the bottom:
Becket Adams, commentary writer
Would hope for: Elizabeth Warren. She’s the Wile E. Coyote of the Democratic field. Too clever by half and her own worst enemy. The DNA test is the worst self-own that any 2020 Democrat has committed in a long, long time. At this rate, Trump won’t even need to say anything. All he’ll have to do is point, and everyone will get the punchline.
Would fear: Joe Biden. He may be Uncle Joe now, but he’s still the mean son-of-a-bitch who demolished Robert Bork and tried to do the same to Clarence Thomas. Also, people like him.
Katie Anderson, commentary intern
If I were Trump, I would want to run against Rep. Tim Ryan, because he would depress the Democratic base, thanks to his record: He has voted to loosen restrictions on gun purchases, and once earned an A from the National Rifle Association. He voted to ban partial-birth abortion, except to save the mother. Additionally, Ryan fails to check all the important boxes for the Left: He’s straight, white, and male who also challenged Nancy Pelosi for speaker of the House.
The person I wouldn’t want to run against is Sen. Kamala Harris, who is both African-American and a woman. Because identity politics will be on the top of Democrats’ mind, she will be the top candidate who will also fight for abortion (she’s been buddy-buddy with Planned Parenthood for years), universal healthcare, and DACA.
Erin Dunne, commentary writer
Would hope for: Kirsten Gillibrand. Too bland, too much like Hillary, and has too little to make her the people’s hero that people want in politicians.
Would fear: Amy Klobuchar. She’s a Midwesterner and a woman who doesn’t do the attention-grabbing nonsense other Democrats seem unable to resist. She’s kept her head in recent flashpoints and won’t alienate voters on key issues. She’s the most likely of all the Democrats to win the Rust Belt states that were key to giving Trump the White House. She also is the anti-Trump.
David Freddoso, op-ed editor
I’d most want to run against Kamala Harris. You may think it hard for Trump to make someone else look unethical and callous toward the afflicted, but Harris absolutely fit that bill in her prosecutorial career. She left a trail of destruction, with grave consequences for innocent people. It’s all there waiting to be exploited. Her recent anti-Catholic jab at the Knights of Columbus will also guarantee that most of the people in my circles back home who voted for Trump with reservations last time will do it again this time without so much as a second thought.
People are also going to be asking about Willie Brown. Sorry, but it has to be said, and Democrats will be discussing it in Iowa before Trump gets a crack at her. Finally, her home state is important, but it’s also an isolated and non-representative state that Trump can afford to lose by 70 or 80 points.
I’d least want to run against former Vice President Joe Biden. If you wonder why, just watch him in that 2012 debate with Paul Ryan. He may be the only person who can out-Trump Trump when he has to.
More importantly, he is not so far left, anti-religious, and bloodthirsty on abortion as to scare the rest of the country away. He tried to get the Obama administration to back off on the Little Sisters of the Poor, according to at least one account that I read.
I would not vote for Biden personally, but I would not feel like the world was ending if he won, and if I feel that way, then many ethnic Midwesterners suspicious of Trump and less conservative than myself will probably feel the same way. This is why I think Biden can halt, for at least a cycle or two, Democrats’ bloodletting in the Midwest. The only other Democrat capable of this, in my opinion, is Amy Klobuchar, who is too unknown and less likely to advance past the primary.
Madeline Fry, culture writer
Would hope for: Tulsi Gabbard is too centrist to win the Democratic nomination, but if she did, she’d have to continue to answer for her controversial foreign policy decisions, like that meeting with Syrian President Bashar Assad, and her past stance on gay marriage. Other politicians have overcome worse, but Gabbard doesn’t seem to know how.
Would fear: Sen. Bernie Sanders is older than Joe Biden and pretty much every other white male gunning for the presidency. Yet, despite his age, the Vermont independent polls in the top three Democratic presidential contenders; he’s still beloved by the youth, more of whom are registering to vote; and while other Democrats tout their support for government-financed healthcare, Sanders can campaign on having led the charge for “Medicare for All.”
Siraj Hashmi, commentary writer
Would hope for: Terry McAuliffe. The former Virginia governor, who has flirted with a 2020 run, worked alongside Ralph Northam, the embattled governor who seemed to endorse infanticide before a racist medical school yearbook photo surfaced, and was an acolyte for Bill and Hillary Clinton, Trump’s archnemeses. In addition to being a corrupt governor who was under FBI investigation, McAuliffe will find it hard to wipe the stain of working alongside an alleged racist and even harder to erase his past devotion to the Clintons.
Would fear: Beto O’Rourke. “But why?” you ask. The answer is simple: He’s young with a relatively clean past, apart from the fact that he’s a crony capitalist. A socialist? So what? According to a CNN poll, 54 percent of Iowa Democrats want a candidate who can beat President Trump; meanwhile, 40 percent said they want a candidate who shares their positions on major issues. That could be a boon for any Democrat, but especially O’Rourke, a baby-faced newcomer who isn’t known for holding a strong stance on any of the major issues. He has the Obama vibe, at least with many in the media, and that might be enough to bring back independents who voted for Obama in 2008 and Trump in 2016.
Quin Hillyer, senior commentary writer
If I were Trump, thank goodness I’m not, I would most want to run against Elizabeth Warren, who has become a laughingstock and would have no appeal to middle America.
I would least want to run against Mitch Landrieu, who can pretend to be a moderate and a coalition builder and who is one of the most effective political speakers I have heard in the past two decades.
Tiana Lowe, commentary writer
Would hope for: Robert Francis O’Rourke. Despite the fact that he hasn’t even announced that he’s running for president, he’s continually come in third in national primary polling. But given that he just came out of an election against one of the most unlikable Republicans in the country (sorry, Ted Cruz) the buzz for O’Rourke is stronger now than it’ll ever be. To date, O’Rourke has served as a mediocre-looking canvas for liberals missing the natural charisma and charm of Barack Obama. But the more details emerge about O’Rourke’s life — fleeing from a drunk car wreck at 26, his billionaire wife, his lackluster congressional record — the less impressive he seems. Plus, can’t you imagine Trump having a field day with such a mockable young man?
Would fear: Amy Klobuchar. The 57 percent of Americans who say they’ve ruled out voting for Trump may reconsider if the Democrats nominate a candidate who wants to abolish private healthcare, enact the “Green New Deal,” legalize third-trimester abortion, and abandon Israel. Thus far, Klobuchar seems to be the only presumptive candidate to stand her ground and refuse to fall in the new, increasingly socialist party line. Klobuchar is the dark horse of the race, a calm prosecutor with Rust Belt appeal who doesn’t resort to desperate social media antics or low blows in the Senate Judiciary Committee, and when paired against Trump, her preternatural calmness may just be her strength.
Tom Rogan, commentary writer
Would hope for: Bill de Blasio. I would have put Elizabeth Warren in a close second, but considering Trump’s alienation of female suburban voters in the midterm elections, he is more vulnerable against her than de Blasio. Why de Blasio? Because he is so far to the left of the political center as to scare even those independents who strongly dislike Trump. You can see the Trump campaign catch lines now: “Billing you, de Blasio,” “Big bills de Blasio,” “Mugger de Blasio,” etc.
Would fear most: Joe Biden. Speaks to an era of relative stability, a charismatic moderate who could get under Trump’s skin and appeal to independents. Would present himself as the dealmaker candidate ready to bridge partisan divides.
Jason Russell, contributors editor
Trump should be hoping for an Elizabeth Warren nomination; with her sketchy, overtly self-interested past and progressive ideals, the general election would be a re-run of 2016. She might peel off some populists by promising government-funded healthcare but not enough to overcome Trump’s loud populism on everything from immigration to foreign policy.
Trump should be most afraid of a one-on-one battle against independent candidate Howard Schultz. Since that won’t happen, he should be most afraid of former Vice President Joe Biden, who fights, entertains the Democratic base, and already polls well against Trump.
Eddie Scarry, commentary writer
Would hope for: Cory Booker. Like any political figure the news media adore, the New Jersey senator believes he really is special, and there is no surer sign of an oncoming campaign implosion than a candidate who decides to run because he believes the media hype about himself. Has anyone seen Booker endure a moment of serious scrutiny yet? When that time comes, he’ll probably choke.
Would fear: Joe Biden. He has the same knack for persuading large audiences that Trump does. For all of Trump’s successes on the economy in his first term, the disruption his presidency has caused, even if it was for the best, has taken a toll on the nation’s psyche. Biden could convincingly argue that it’s time for us to exit the ride before it collapses and we all die.
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My answer: While Bernie Sanders would’ve won had he run in 2016, he would certainly lose in 2020. To win, Democrats need to about 85,000 net votes in Pennsylvania and Michigan, which, if the 2018 results tell us anything, mostly involves not scaring off suburban moderates. Bernie’s wacky-professor mien and socialist agenda is the perfect formula for putting off these swing voters.
Trump should most fear Kirsten Gillibrand because she has no beliefs. Trump’s negatives are high enough that the Democratic base will be motivated no matter what. By not believing in anything, the New York senator will avoid riling up the working-class, conservative, or establishment center-right electorates.
