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

March 3, 2017
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President Donald Trump built his 2016 campaign on the promise to his supporters that he would not be beholden to special interests because he was "self-funding my own campaign." And while Trump indeed broke small donation records, he is approaching 2020 with a different tack, Politico reports.

Take, for example, Trump's about-face on hedge fund billionaire Paul Singer, who supported Marco Rubio and an anti-Trump PAC during the Republican primary. At the time, Trump slammed Singer as having a "lotta controversy." After winning the election, Singer reportedly donated $5,000 to Trump's transition team and $1 million to his inaugural committee — then asked Trump for a meeting, and got it.

And "Singer … is just one of many GOP donors who have been the subject of entreaties from Trump and his closest confidants," Politico writes, "and the charm offensive appears to be paying dividends."

Many of Trump's Cabinet members were also top donors, and other mega-donors, including those who initially backed his rivals, are also finding themselves in the position to accept high offices. That includes Todd Ricketts, for deputy commerce secretary, and Trump's expected ambassador to Canada, Kelly Knight Craft. "Do you think if you were not a multibillionaire, if your family has not made hundreds of millions of dollars of contributions to the Republican Party, that you would be sitting here today?" Sen. Bernie Sanders (I-Vt.) even accused Trump's education secretary, Betsy DeVos, at her conformation hearing in January.

"Drain the swamp? He's filing the swamp," said Clinton family fundraiser and Virginia Gov. Terry McAuliffe. "[Trump] ran on something else. The people whom he attacked are the same people he's put in charge of the government. That is hypocritical. You can call it whatever you want. But don't think for one second people aren't paying attention."

But others see Trump's move as a sly one. A person who works with major Republican donors explained to Politico: "Trump has been very methodical and clever. The process began within days of the election." Read more about Trump's financial preparations for the next election here. Jeva Lange

March 1, 2017

Oprah Winfrey indicated she has not ruled out the possibility of running for president while speaking with David Rubenstein on the season two premiere of Bloomberg Television's The David Rubenstein Show: Peer-to-Peer Conversations.

"I never considered the question, even a possibility," Winfrey said. "I just thought, oh. Oh."

"Right, because it's clear that you don't need government experience to be elected president of the United States," Rubenstein said.

"That's what I thought," agreed Winfrey. "I thought, oh gee, I don't have the experience, I don't know enough. And now I'm thinking: Oh."

Oprah 2020? Watch below. Jeva Lange