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Presidential elections have a context. Without the context, what I’m about to say will sound crazy. Elections happen in a particular time and place in history. They have actual people and personalities. And, as we all know, they have consequences and repercussions. a context. Without the context, what I’m about to say will sound crazy. Elections happen in a particular time and place in history. They have actual people and personalities. And, as we all know, they have consequences and repercussions. If Donald J. Trump runs for re-election — which every single incumbent has done in my lifetime — nothing about the 2020 presidential election is going to be normal. The old rules won’t apply. The traditional norms and standards of campaigns, primaries, and debates will all be thrown out the window. That has to be the starting point. Then, we have to keep in mind that Democrats underestimate successful Republicans at their own peril. Nobody thought George W. Bush could ever become governor of Texas. Then he beat Ann Richards — a cult figure in the state — by 8 points. When he won his re-election as governor, Bush got an astounding 69 percent of the vote. Al Gore was a virtual shoe-in to win the presidency in 2000. A two-term vice president who inherited a healthy economy, Gore then lost in a head-to-head race with Bush. For four straight years, Democrats mocked him as an inarticulate fool. With his approval rating tanking as the Iraq War became an obvious quagmire, Bush still won re-election against then-Sen. John Kerry. Say what you want, George W. Bush was a nearly unbeatable politician. Trump is a Godzilla of a political opponent. He wields his 46.5 million Twitter followers, 23 million Facebook followers, and 8.2 million Instagram followers to not just dominate and shape every single news cycle, but to mock and ridicule his opponents. He has a media machine — Fox News, Breitbart, and increasingly places like the Wall Street Journal — that are more than willing to amplify his message. And, at the receiving end, there are millions of people who will believe him and vote for him. He literally told over 2,000 lies in his first year in office yet consistently goes on about “fake news.” On Wednesday, he had the gall to say he wished the United States had tougher libel laws to hold people accountable for their dishonest attacks. Trump won 30 different states in the 2016 general election. Sixty-three million people voted for him. Even though he was the least popular presidential candidate in the history of modern politics, he won. He’s now the president of the United States. And he got there even after more than a dozen women came forward to say he sexually assaulted or harassed them. Trump was elected even after a recording was released of him admitting he sexually assaults women. He was elected even after mocking Sen. John McCain, R-Ariz., for being a prisoner of war. He was elected even after blaming the questioning he received from a debate moderator on her menstrual cycle. He was elected even after allegations circulated that he brutally raped and assaulted his first wife in a rage after a scalp reduction surgery. Even after the Ku Klux Klan endorsed him and Neo-Nazis openly attended his campaign events, Trump won. He is formidable. Ask Jeb Bush. Ask Hillary Clinton. Their political careers are over. When Trump beats you in a head-to-head match-up, it’s hard to recover. If Trump weren’t the opponent, a traditional Democratic primary, full of governors most of the nation has never heard of and senators they are likely tired of, might produce a candidate who could defeat the Republican incumbent. Even against Trump, it’s still possible that a traditional Democrat — an upstart in the party, or even an established member — could slog their way through a tough primary, capture the nation’s attention, rise up, and beat him. But going against the president’s massive online influence and the right-wing media machine that allows him to dictate so much coverage is far more difficult than it appears. As a result, there are only a few particular people who I believe can easily defeat Trump in a presidential election, who could enter the race with a good fighting chance.

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An ideal opponent to face off against the president will need to come to the race with four things in hand. Without these four things going for them, any candidate will struggle. An enormous social media following across all platforms. An established, core base of support that already exists. They need to be able to pack a stadium without Beyoncé or Bruce Springsteen opening up. The ability to present a strong contrast in character and personality to Trump. A history of organizing people, because the Democratic Party is a mess. to face off against the president will need to come to the race with four things in hand. Without these four things going for them, any candidate will struggle. With that said, let me tell you who would absolutely mop the floor with Trump — it wouldn’t even be close: Barack Obama. Just to be clear, I’m not saying that as an endorsement of Obama’s politics or of a third presidential term. I’m just saying he has all four of those factors and is actually the only politician in America with more followers online than Trump — he actually has twice as many as Trump. But Obama can’t run (and probably wouldn’t if he could). So, who else is there? Love the idea or hate it, one name has been on everyone’s minds this week: Oprah Winfrey. After Oprah’s rousing speech at the Golden Globes on Sunday, the rumors about her running for president reached a fever pitch. For the first time, even Gayle King and Stedman Graham hinted at the real possibility that Winfrey was considering a run for the highest office in the land. Enter Rasmussen, the polling firm. They seem to tilt a bit conservative and often give Trump an approval rating higher than most others. That’s why Rasmussen is often called Trump’s favorite poll. That’s part of the reason a poll Rasmussen on Wednesday was such a big deal. Rasmussen decided to find out what people actually thought about a 2020 presidential match-up between Oprah Winfrey and Donald Trump. In Trump’s favorite poll, in a head-to-head match-up against him, Winfrey beats Trump by 10 points. My guess is that when we see other companies release their polling numbers on the potential match-up between Winfrey and Trump, she’ll beat him by an even wider margin. I’m elevating Winfrey in the discussion because she fits all four factors I think are required for someone to have a strong victory against Trump. Her social media reach rivals his. She has a deeply devoted core base of support to lean on — she can already pack stadiums from coast to coast. While she and Trump are both billionaires, they arrived at their positions in wildly different ways. Not only that, but Oprah’s brand is kindness and generosity; she’s the anti-Trump in that sense. While Oprah is not a traditional political organizer, she has organized people for events, subscriptions, clubs, and causes for decades. She knows how to move people.

President Barack Obama walks off stage with his wife Michelle and daughter Malia after delivering a farewell speech to the nation on Jan. 10, 2017, in Chicago. Photo: Scott Olson/Getty Images/Getty Images



Oprah Winfrey is not the only one who fits the bill. not the only one who fits the bill. Speaking of a beloved black woman, Michelle Obama could also defeat Trump. Again, this is not me endorsing her. She’s said repeatedly that she would not run, but if she did, she would win. She is one of the most popular figures in the country. Even when Barack Obama’s approval rating struggled, her approval rating stayed in the mid-60s. Like Winfrey, Michelle Obama has more social media followers than any active politician in the nation, other than Trump. She doesn’t have as many as Trump, but her reach is far and wide. She has the deeply committed core of supporters that a candidate will need to win. She’s an amazing speaker and can already draw a huge crowd wherever she goes. She is as unlike Trump as human being could possibly be, and she understands what it takes to win a presidential campaign. Then there are others, like Sen. Bernie Sanders. From the start of the 2016 presidential cycle until the very end, the Vermont independent beat Trump in head-to-head polling match-ups. Sanders continues to defeat Trump in hypothetical match-ups. No active politician in the country other than Trump has as many followers on social media as Sanders. His base is as devout as any political leader in the nation. Sanders proved throughout his campaign that he can pack stadiums. Sanders is as different from Trump as another old white man could possibly be. And lastly, and perhaps most importantly, Sanders proved himself to be an amazing fundraiser and political organizer. Those skills, with his preexisting network, will be invaluable if he opts to run again. Then there’s Joe Biden. Biden is an expert as losing presidential campaigns. He ran for the Democratic nomination and lost in 1988. He ran again 20 years later in 2008 and lost again. But his eight years in the Obama administration endeared him to the nation in a way that Biden never enjoyed until now. His approval rating has grown even more since he left office. In most polls, Biden also wins by a large margin in a head-to-head match-up against Trump. While Biden has the smallest social media reach among the four people I’ve named, he still has more than almost every active Democrat except for Sens. Cory Booker, D-N.J., and Elizabeth Warren, D-Mass., but might be less adept at using it — and that matters. Does Biden have a deeply devoted base? I’m not so sure — though maybe he’s absorbed some of Obama’s base. Could Biden pack stadiums? He draws good crowds, but stadiums? I’m not so sure about that either. Is he a good fundraiser or organizer without Obama? It’s hard to say. Biden’s origin story and life’s work are altogether different than that of Trump — and that contrast between the two men could be easily made, but Biden is also known for gaffes and being a little touchy-feely with women. Especially in today’s climate and especially against Trump, that’s a problem. There are others still who would be fascinating to watch run. The Democratic primary would be strengthened if Booker and Warren ran for the nomination. They have the largest following online of any active Democrats. They each present the strong political and personal contrast needed up against Trump. They are both great public speakers and are masters of the issues that they care most about. And I think in any traditional election, they’d be perfect nominees for the Democratic Party. But can they pack a stadium full of people without Beyoncé opening and Jay-Z closing? Not today, they couldn’t. What experience do they have organizing people on the national level? Trump won 30 different states. How will Booker and Warren play in those states that they need to flip over to the Democrats? It’s hard to say.

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