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The 2020 election is still over 1,000 days away, but President Trump is already floating, and ruling out, possible challengers, Politico reports. "He's always asking people, 'Who do you think is going to run against me?'" said one aide who has personally heard such musings.

Two of the Democratic Party's most high-profile potential candidates, Vermont Sen. Bernie Sanders and Massachusetts Sen. Elizabeth Warren, don't cause Trump to break a sweat, Politico notes. Despite Sanders being rated as the most popular politician in the country by several polls last year, and Public Policy Polling predicting in July that he could beat Trump by 13 points in a head-to-head general election, Trump dismissed Sanders, 76, as being too old to run again. Warren would also be "easy to beat," Trump has reportedly said, and his team is similarly unconcerned about Sen. Kirsten Gillibrand (D-N.Y.).

"If the Democrats think a socialist or a liberal professor from Massachusetts are a path to victory, we're happy to help them highlight that, because we don't think that is in tune with the vast majority of Americans," a Republican National Committee spokeswoman said. Sen. Kamala Harris (D-Calif.), another potential 2020 candidate, was not on Trump's "radar yet," Politico notes.

Trump hasn't ruled out every potential challenger, though. His team is reportedly concerned about former Vice President Joe Biden, fellow billionaire Mark Cuban — and Oprah Winfrey. "Oprah would be a problem," a Republican strategist told Politico. "She'd be their best. She's ubiquitous, she's black, she has crossover appeal, and she probably clears a lot of the field out." Jeva Lange

December 20, 2017

If you are still nursing a figurative hangover from the never-ending 2016 presidential race, new polling from NBC News/Wall Street Journal may trigger some emotional discomfort, but early numbers for President Trump's presumed 2020 re-election campaign are in, and they aren't great. Only 18 percent of Americans say they would definitely support Trump next go-around, the poll found, while another 18 percent would probably back him, 38 percent would definitely vote against him, and 14 percent would probably vote for whatever Democrat is on the ballot.

If you're keeping score, that's 36 percent for Trump, 52 percent for Generic Democrat.

In comparison, only 14 percent of Americans told NBC/WSJ pollsters they would definitely vote for a generic Republican over President Bill Clinton in December 1993, after a tough first year for Clinton. There is a predictable partisan split in the Trump 2020 numbers, with 43 percent of Republicans saying they will definitely support Trump and 73 percent of Democrats saying they will definitely vote against him. Trump has lost ground among key demographics, with only 47 percent of white voters without a college degree saying they will definitely or probably vote for Trump and 43 percent of rural voters giving a definite thumbs-up.

The NBC/WSJ poll was conducted Dec. 13-15 among 900 adults and it has an overall margin of error of ±3.3 percentage points. Peter Weber

November 20, 2017
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Here is another name to add to your list of potential 2020 candidates: New York City Mayor Bill de Blasio.

De Blasio will travel to Iowa in December in a move many interpret as testing the waters on a national next step, Politico reports. Although de Blasio denies he is running for president, he has also signaled in interviews that his sights are set on much more than just his city: "I think the Democratic Party is ill-defined right now and I think it's ill-defined because it's lost touch with what should be its core ideology," he said Sunday. "Because it's ill-defined, they're not winning elections and the two go together."

While de Blasio ran Hillary Clinton's Senate campaign in 2000, Politico reports that he is now "fully embracing the Sen. Bernie Sanders wing of the party." De Blasio's trip to Iowa is paid for by Progress Iowa, which, as the name implies, champions progressive candidates. The mayor is scheduled to be the headliner of the organization's holiday party, "the group's largest event of the year and its most important outlet for fundraising," Politico notes.

Hizzoner waved off speculation about his trip as being "infantile," but he didn't deny he is looking at the big picture these days. "The big future of this country is when a handful more states start to move and they include Texas and Arizona and Florida too," he said. "Those will be decisive to the future of the country and the future of New York State and New York City. That change is available — I'm saying that as a Democrat and a progressive — that change is available to us and I'm obsessed with it." Read more about a possible de Blasio 2020 bid at Politico. Jeva Lange

August 25, 2017
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Ohio Gov. John Kasich (R) could challenge President Trump in 2020 on a bipartisan ticket with Colorado Gov. John Hickenlooper (D), people familiar with the plans told Axios.

Kasich, who ran unsuccessfully in the 2016 Republican primary, would likely be at the top of the ticket, and the two Johns would focus their campaign on immigration and job creation in the face of automation. While one strategist told Axios that "no Dem wants Kasich anywhere near our ticket," another operative said "our political system is completely broken. Something big and historic needs to happen to break the logjam. I'm a big Dem but I'm for anything that ... does away with this hyper-partisanship on both sides that is paralyzing our government."

Read the full scoop at Axios. Jeva Lange

May 19, 2017
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Former Vice President Joe Biden is still talking about what it would've been like if he'd run for president in 2016. At a SALT hedge conference Thursday night in Las Vegas, Biden reportedly took a dig at one of the Democrats who did run, Hillary Clinton. "I never thought she was a great candidate," Biden said. "I thought I was a great candidate." Biden later added that Clinton still "would have been a really good president."

Biden ultimately decided not to run in 2016 because he and his family were still grappling with 2015 death of Biden's son Beau from brain cancer. When asked Thursday about the possibility of running for president in 2020, Biden didn't totally rule it out. "Could I? Yes. Would I? Probably not," Biden said, later suggesting he "may very well do it."

Biden will be nearly 78 years old by the next presidential election. Becca Stanek

May 9, 2017
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As Facebook CEO Mark Zuckerberg criss-crosses the country with the goal of meeting people from all 50 states, he has naturally left behind a wake of rumors that he will run for president in 2020. But if that's the case, why is he intentionally shirking the media during his seemingly made-for-media appearances?

Facebook told Axios that Zuckerberg wants to be able to meet with people who can be "candid" without the glare of the press. And "while the Zuckerberg-for-president story has been overhyped, his friends think he may run for something one day, so these appearances help him connect to all types of potential voters and give him chance to get better at these sorts of appearances without the blinding glare of constant press attention," Axios adds in its own analysis of the situation.

Even though "Zuckerberg had dinner with a family in Ohio, and these days, that's enough to have some people talking about a presidential run," as Veuer reports, Axios suggests the tour is more like a practice run to get Zuckerberg comfortable and familiar with the versions of America that exist outside Silicon Valley.

"Zuckerberg has devoted significant time over the last several years to improving as a public speaker," Axios writes, noting there is still room for improvement. Read more about why Zuckerberg is shaking off the press at Axios. Jeva Lange

March 15, 2017
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Former Maryland Gov. Martin O'Malley might not have made it terribly far in the Democratic primary against Hillary Clinton and Sen. Bernie Sanders, but he's already testing the waters for 2020, Politico reports.

O'Malley's leadership PAC commissioned a Public Policy Polling survey to feel out where caucus-goers in Iowa stand when considering a field of nine potential Democratic candidates. O'Malley led with 18 percent, followed by New Jersey Sen. Cory Booker, who had 17 percent, and Minnesota Sen. Amy Klobuchar, who had 11 percent.

Former Housing Secretary Julian Castro, New York Gov. Andrew Cuomo, New York Sen. Kirsten Gillibrand, California Sen. Kamala Harris, Facebook COO Sheryl Sandberg, and Starbucks CEO Howard Schultz were also included in the poll, but each received less than 10 percent. Curiously, some major potential 2020 competitors were left out of the poll, including Massachusetts Sen. Elizabeth Warren, Ohio Sen. Sherrod Brown, and Sanders, Politico points out.

The overwhelming opinion, though, is one of indecision: "Not sure" got 32 percent of the vote.

O'Malley said in January that he "just might" run in 2020. He dropped out of the 2016 race after earning less than one percent in Iowa last February. Jeva Lange

March 14, 2017

Former Senate Minority Leader Harry Reid retired in December after more than 15 years in office, and he used the final weeks before his departure looking for a way to rebuild the bruised Democratic Party.

For Reid, the solution was Sen. Elizabeth Warren (D-Mass.):

Reid brought Warren onto the Democratic Senate leadership team in 2014, and she was one of the people he most trusted to keep the Senate caucus on its bearings through the difficult weather ahead. Shortly before Thanksgiving, he summoned Warren to the minority leader's office. When she arrived, the room was littered with art supplies; on an easel was a half-finished portrait of Reid that would be unveiled at his retirement party the following month. Its subject was preoccupied with the future of the party to which he had dedicated decades of his life. Reid told Warren she needed to think seriously about running for president in 2020. "He was worried in November," Warren told me recently. "For me, it was so important to make clear: We will fight back — we will fight back. We're not here to make this normal." [The New York Times Magazine]

Read more about how the Democrats are rebuilding, looking ahead, and learning the word "no" at The New York Times Magazine. Jeva Lange

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