Who Challenges Trump In 2020?

May 1st, 2017 | T. Carter

The Democrats lost to a popular uprising of tired Americans in November, but they'll be looking to regain their relevancy in 2020—even if they don't beat Donald Trump. They will still be looking to beat Donald Trump, but they will need to hedge their bets in case they don't. They will need a candidate who speaks to the right number of Americans and can rebuild their party's decrepit base. That candidate could come in any number of forms. It could be a well established heavyweight or a Trump-style outsider who promises to do things differently.

The Heavyweights

Elizabeth Warren

The most obvious name floating around among Democrats is Elizabeth Warren, a woman with a shameless style similar to Donald Trump, but who swings so far to the fringes on some issues that she may appear unhinged to a majority of American voters. She wouldn't be able to immunize herself against the backlash that would be directed at her because of her own outspokenness, like Donald Trump has successfully managed to do. That could make her a liability for Democrats, but a vast portion of Democrats will be enthused and invigorated by her.

Following a wave of speculation last month, Warren told Rachel Maddow that she would not be running in 2020, but almost every major candidate before her has said the same. In due time and as Democrat donors and some establishmentarians create a movement on her behalf, she will change her mind.

Andrew Cuomo

New York's Democrat Governor will likely throw his name into the race for 2020. Cuomo's brother, Chris Cuomo, is a popular anchor at the fake news network, CNN, and the Governor has had a positive amount of coverage at most of American's mainstream news networks since winning in 2010. Cuomo and Democrats will be excited to challenge Trump on his home turf and play on the fact that Trump lost his own state in the 2016 election.

Cuomo even worked under the Clinton Administration in 1993 as an assistant secretary and then as Secretary Of HUD between 1997 and 2001. His connections go deep, but his Clinton connections could hurt him in the wake of growing resentment and anger toward the Clinton family. Possibly by 2020, Americans will have forgotten all of the Clinton corruption and the family's deep connections to Russia. Cuomo is also married to a Kennedy.

In 2014, Cuomo said “extreme conservatives” have “no place” in New York.

Al Franken

The former comedian turned Senator recently enjoyed show-boating during the confirmation hearings of Neil Gorsuch. He enjoys getting under the skin of conservatives, and Democrats enjoy watching him do it.

Franken wants universal healthcare, just as Bernie Sanders did. He has wanted to cut student loan rates, increase Social Security payments, cut subsidies to oil companies and make college more affordable. Franken would likely appeal to a large portion of the Sanders base with his policies, giving him a good chance to rise high and become a viable contender in the Democratic primaries and general election. If Trump should fear anyone, it should be Al Franken. Franken may be the very next version of Bernie Sanders.

Like others before him who ended up running for president, Franken has said he will not run in 2020. Don't count on that being true.

Caroline Kennedy

Just imagine another Kennedy running for president and that Kennedy being a woman. Caroline Kennedy is a member of the Kennedy family and their name alone could carry her to the top of the Democratic primaries. She could send Trump running for his money.

Caroline Kennedy isn't just a Kennedy, she is the daughter of John F. Kennedy. She was Barack Obama's ambassador to Japan and in 2008 she wrote that Obama inspired her like her father. In 2008, there was also speculation that Kennedy could be a contender for VP and might join the Obama ticket.

Beware of Caroline Kennedy in 2020. She will make waves.

Cory Booker

Most Americans know who Cory Booker is, which is rare for any Senator—especially one from New Jersey. He has made a name for himself over the years and has political connections across the country that could take him all the way to the White House. Booker could play the race card and he could use his massive trove of political capital to unseat his Democratic rivals and Donald Trump.

In 2013, Booker had 75% name recognition and a 66% favorability rating in his home state. He is well-known and well liked by enough Americans to make Donald Trump wince.

Michelle Obama

Don't count her out. Michelle Obama could easily pull off what Hillary Clinton could not. Whether we Americans want to admit it or not, Barack Obama is still a popular president and Democrats would be salivating at the chance to re-live his legacy after four years of Donald Trump.

If the Democrats could take vengeance on Trump and his supporters by returning an Obama to office, they would. Under a Michelle Obama presidency, Barack Obama would be where Bill Clinton wanted to be in 2017. He would not be president again, but he would definitely influence policy.

Putting Michelle Obama in the Oval Office wouldn't just be about putting Michelle Obama in the Oval Office, it would be about putting Barack Obama back into the White House. Democrats have already dreamed up fairy tales about another Obama presidency. This could be one of the surest ways to beat Donald Trump. We shouldn't put it past Democrats to try it.  

The Superstars

Oprah Winfrey

She may be past her prime, but Oprah is still regarded as one of America's most powerful icons. In the 1980s, she famously asked Donald Trump if he would ever run for president, so an Oprah run would have the smell of destiny to it.

Her star has faded over the years, but Oprah has all the right identity cards that Democrats have traditionally looked for. She is black. She is successful and she is a woman. To boot, she has almost the same star power as Donald Trump did. In a Democratic primary, Oprah would undoubtedly have the same advantages Trump had in the Republican primaries. The bigger the field of contenders, the more likely it would be for a celebrity to squeak out a victory.

George Clooney

He has said he probably won't do it, but the Democratic media establishment has already thrown his name into the draw box. He has been sold by some left-wing writers as “the candidate to beat Trump” and he seems to have taken interesting measures to align himself with some DC power-brokers. He also married a powerful human rights lawyer who has taken on several high profile battles.

Clooney has massive name recognition, popularity, wealth and connections. His history is also filled with humanitarian initiatives and actions that would turbo charge his curriculum vitae. After the earthquake in Haiti, Clooney was there. To remind the world about genocide in Darfur and in Armenia, Clooney never skipped a beat. In 2015, he also made comments similar to Donald Trump by stating that the Syrian conflict was “too complicated” and that the US should stay out of it. In 2016, Clooney thanked Angela Merkel for Germany's open-door policy on refugees.

Clooney may be too interested in keeping his Hollywood legacy untarnished from a presidential run and the dirty mudslinging that comes with it, but if he thinks he could win and build a new legacy as America's 46th president, he might take the shot.

Mark Cuban

Out of all the potential candidates listed here, Mark Cuban has the lowest chance of winning in a Democratic primary. He doesn't have any populist appeal, or a level of celebrity like Oprah or Clooney that would sail him to the top of a field of candidates.

On issues that matter most to Bernie Democrats and moderates, Cuban would be considered too right-wing. Aside from his hatred of Donald Trump, Cuban really doesn't have much in common with Democrats. It would take five minutes into an exploratory committee for him to realize this and not even bother. However, he could still run in a Democratic primary just to show off or boost his own profile.

Democrats will be doing what they can to beat Trump in 2020. Trump and Republicans should be prepared for one of these candidates to pose a threat to Trump's second term. If Trump can't elevate his approval rating above 50% by 2019, he should be worried.