It was late on a Saturday night in May, and Marianne Williamson — the best-selling self-help author, spiritual sage and one of 23 souls vying to be the Democrats’ next presidential nominee — was sitting at a kitchen island in a large home on the western edge of Des Moines, nursing a generous glass of red wine. Her traveling aide, an extremely tall young woman named Tandra, was seated cross-legged on the floor a few feet away, next to a basket of fuzzy baby chickens.Williamson was winding down after a long night of campaigning. She had just ministered to the guests at a reception held in her honor, holding forth on a back porch for an hour and a half about the “moral and spiritual awakening” she vowed to lead from the White House in order to “heal the low-level emotional civil war” underway in a broken America. Now the party was breaking up, most of the guests had left and the candidate seemed somewhat forlorn. “I’m finding this a bit confusing,” Williamson told me, looking up from the island.She was trying to make sense of the rules determining who would qualify for a place in the Democratic presidential debates in late June. At first, she believed she had cleared the Democratic National Committee’s threshold for participation, having received the requisite donations from 65,000 people. “But now they’re saying something new about polls,” she said.ImageMarianne Williamson campaigning at the Capital City Pride Fest in Des Moines on June 8.CreditScott Olson/Getty ImagesI first met Williamson, who is 66, five years ago, during her only previous foray into electoral politics. She was then one of 18 candidates running for a congressional seat in the Botox Belt of Southern California — Beverly Hills, Malibu, Bel Air — long held by the retiring Democrat Henry Waxman. Williamson was perhaps the best known among them: spiritual counselor to Oprah Winfrey, guru to Cher and even an officiant at one of Elizabeth Taylor’s (eight) weddings. She won support from Katy Perry and Alanis Morissette, and her campaign events turned up the occasional Kardashian. But this had not been enough to send Williamson to Congress. And so now Williamson was doing what every Democratic politician or candidate, successful or otherwise, seemed to be doing in 2019: running for president.I had seen four of them in Iowa in the previous 36 hours, and Pete Buttigieg over the border in Minnesota two nights earlier: Elizabeth Warren in Ames and Iowa Falls on Friday, Amy Klobuchar in Des Moines on Saturday morning, Bernie Sanders in Ames that afternoon and Klobuchar again in Iowa City that evening before I returned to Des Moines to drop in on Williamson. When Williamson first announced her exploratory committee in November, her bid to be the Mike Gravel of 2020 — the self-assured oddball who kept the debates interesting — was a solid one: The only declared competition in the snowball’s-chance lane was John Delaney, a replacement-level Maryland congressman, and Andrew Yang, a New York businessman and universal-basic-income advocate who has said he hopes to campaign via hologram in some states.But six months later, any aspiring Mike Gravel hoping to grab a percent or two in the polls had to compete with multiple Western governors (John Hickenlooper, Steve Bullock, Jay Inslee) and senators (Kirsten Gillibrand, Cory Booker), a Housing and Urban Development secretary (Julián Castro) and even the 89-year-old Gravel himself (who was dragooned into running again by a pair of teenage political activists). The border between curiosities and contenders had never seemed so porous, and new candidates seemed to be parachuting in every week; there was a report the day before that Mayor Bill de Blasio of New York would soon be joining the race.“The more the merrier, right?” Klobuchar, an ostensibly formidable hopeful who was polling in very low single digits, told me after a rally in an Iowa City restaurant. She smirked and shook her head. “That’s what our line is, right?”Theoretically, this open season of a campaign was a boon to nontraditional aspirants like Williamson. Practically speaking, however, it posed all kinds of problems — like the question of how you even got on the debate stage, which seemed to be Williamson’s main preoccupation at this moment. “Do you know anything about how this works?” she asked me.ImageCreditPhoto illustration by Doug ChaykaIf there is something that unites the nearly two dozen Democrats currently in the field, it is that no one, really, knows how this works. It’s a cliché at this point to say that Trump changed politics in 2016, and that everyone — candidates, operatives and media — is still scrambling to understand the implications of his victory. No doubt, Trump humbled the experts (you’d hope) and blew up notions of how politicians should behave and what voters would allow. He also ushered in a free-for-all mentality that might account in part for the “Why not me?” stampede on the Democratic side, which now includes everyone from Obama’s goofy-uncle V.P. on down to the guy live-streaming his visit to the dentist to the spiritual guru sipping wine in front of me as tiny peeps emanated from a basket of chicks. But focusing too much on Trump misses the full degree to which uncertainty has become the overriding new norm — in American life, not just politics. Our notions have changed about what it means to be viable, familiar and authentic as public actors. Politics is just one arena in which this shift has been playing out.Up close, the early race for the Democratic nomination can resemble a mass reconnaissance process, with the candidates as advance troops scouting an electorate that their party so badly misunderstood the last time around. How exactly do you run for president in 2019? What are the rules, and what should you say and who is even listening? At their unruly best, campaigns can be sprawling idea labs. You can learn a lot when no one knows anything.I spent a few weeks trying to divine where exactly this has left the Democrats, both as individual campaigns and as a chaotic body of energized particles. There were big and enthusiastic crowds and campaigns trying to play nice with one another, at least in public (and at least for now). Polls have been mostly steady, with the best-known candidates (Biden, Sanders) at the top, followed by a shifting cast of risers (Warren, Buttigieg, Kamala Harris) and a trailing horde of 1-percenters and vanity candidates bringing up the crowded rear.Candidates have alternately enjoyed media-darling status or wondered why they weren’t breaking through. They hate it when people ask if they’d want to be someone’s vice president or maybe consider (Hickenlooper, Bullock, O’Rourke) running for Senate back home (Colorado, Montana, Texas) instead of running around telling New Hampshire voters how special they and their silly primary are. But there is far less unity among the various campaigns, and sometimes within the candidates’ own heads, about how they plan to engage with voters and, ultimately, campaign against Trump. Beating him has quite obviously been a preoccupation of Democratic voters since the moment of his election, far beyond the typical level of urgency about defeating the incumbent president from the other party. “Electability” has thus become even more of a watchword than usual, leading to circular takes in which voters tend to channel the last pundit they saw yammering on TV about so-and-so’s fund-raising prowess or admirable message discipline.I began my tour of the field on a Saturday morning in early May at a farmers’ market in downtown Des Moines, the first of the season. A few candidates were expected to make the rounds here, including Bernie Sanders, who (per Twitter) was given a bag of mesclun by an admirer before he headed north to Ames for a rally at Iowa State University, in the same venue where I watched Elizabeth Warren a day earlier. At first blush, Sanders 2020 looks and sounds quite a bit like the candidate who monkey-wrenched Hillary’s campaign in 2016. In the student center in Ames, they played Tracy Chapman singing about how finally the tables are starting to turn, while Ben Cohen, the wild-haired Ben and Jerry’s guy, introduced the similarly wild-haired Brooklyn-born Vermonter with flavorful assurance. “He’s been in Washington, in the House and in the Senate, for 30 years,” Cohen said. “He understands the cesspool of what is our political system today. And he’s the guy who therefore will be able to flush the crap down the drain.”ImageSenator Bernie Sanders also made a campaign stop at the Capital City Pride Fest on June 8.CreditScott Olson/Getty ImagesSanders took his usual big swing, aiming less at Trump per se than at the entire corrupt system, including the trivial preoccupations of the idiots who give you the news. “You hear the media, and the media will talk about somebody raised a lot of money today, and somebody attacked somebody else today, and a poll showed this and that today and somebody said something dumb,” Sanders said at the rally. “Or somebody slipped on a banana peel, you know, and, oh, my God, front-page story.”“All right, what is politics about?” Sanders went on. “Think out of the box, not what’s on TV tonight.” He warned the young people in the college crowd against being cynical. “Don’t let your friends tell you that politics is all [expletive], and they don’t have the time to get involved,” he said. “Tell them to stop moaning and groaning.” He walked off to the Doobie Brothers’ “Takin’ It to the Streets.”Circulating in a Bernie crowd, you don’t hear paeans to how their candidate will unite the country and work well across the aisle. There is some frustration too with the expanding chorus of candidates crowding out their message. “Most of these people have no idea why they’re running,” said Ashton Ayers, an Iowa State student from Ottumwa who has supported Sanders since seeing him speak in the basement of a church in 2014. “It’s a big ego trip.”Ayers, who wore a Eugene Debs T-shirt, said he would not commit himself to supporting the eventual Democratic nominee if he or she was not sufficiently progressive. He was unconvinced that Democrats needed to find the candidate the party establishment deemed mainstream enough to take on the incumbent. Recent precedent supports his argument.Obama-loathing Republicans, for instance, nominated future loser Mitt Romney in 2012, and Bush-loathing Democrats opted for nonpresident John Kerry in 2004 (instead of the more inspiring but riskier Howard Dean). If you figure in losing establishment nominees like Hillary Clinton (in 2016) and relative outsiders who actually won (Obama in 2008), there’s a lot to suggest that “safe” has a shaky recent track record. “I’ve voted for many moderate Democrats in general elections,” Ayers told me, including Clinton against Trump. “They always lose.”Later that afternoon, I caught up with Klobuchar at a restaurant in Iowa City where she had just held her own rally. I had encountered her earlier in the day at the Des Moines farmers’ market, where she was gamely posing for photos with a macaw named Jacks perched on her arm. The bird belonged to an Iowa state representative named Ako Abdul-Samad, who was accompanying Klobuchar and feeding the bird sugar snap peas.ImageSenator Amy Klobuchar answers questions at a pizza restaurant in Independence, Iowa, on March 16.CreditChip Somodevilla/Getty ImagesI asked Klobuchar, who had shed the macaw and was now ensconced in a corner booth, whether she was worried that the Democratic field was becoming problematically large. Klobuchar’s main concern, she said, was getting enough of a shot at a televised stage on which to be heard. “After these first two debates, they’re going to have to do something,” she said. (A few weeks later, the D.N.C. announced a higher threshold for the third and fourth debates.)Debates are vital to a candidate like Klobuchar, whose appeal translates much better in formats that reward quick thinking and wit. The Minnesota senator is at her best in conversational settings — inasmuch as conversation is possible at these cattle calls — where she can tout her pragmatic reputation in the Senate and bipartisan bona fides. Klobuchar was the lead Democrat on six bills that became law under President Trump and has been decisively elected three times in an increasingly purple state. Given Clinton’s defeats in previously blue Pennsylvania, Michigan and Wisconsin, it has become imperative for candidates from the Midwest (Klobuchar, Buttigieg) to remind everyone that they possess this geographical fairy dust.“I think you all know, I announced my candidacy in the middle of that snowstorm,” Klobuchar told the crowd in Iowa City. We did all know this; she loves talking about it. “Yep, I could’ve gone inside, but is that what a good Midwesterner would do?” (“Nooo!”) In a Fox News town hall a few days later, Klobuchar tried to give herself the nickname Heartland Amy, though it appears to not yet be sticking.As voters are sounding more like TV pundits, candidates seem more willing than usual to talk like political strategists. They share their particular theories for how they are best equipped to take on Trump. You can of course spin this Rubik’s cube a million different ways and land on a million different profiles that suit any particular argument. For instance, Democrats clearly need to nominate a candidate who is not a white male and who is from the Midwest, preferably from a purple state, and someone whom enough Republicans are down with — or so says the future President Klobuchar.“Hillary Clinton ran a strong race,” Klobuchar said at her rally in Iowa City, drawing cursory applause. “But no one had ever run against the likes of Donald Trump before, right? And now we have all learned.” She spoke with self-assurance, as if she had cracked some elusive code, but her prescriptions seemed a bit anodyne and unoriginal, if not necessarily wrong. “He doesn’t even care who he pisses off, he just sends out a tweet so that he controls the news cycle,” she said. “Sometimes, guys? You ignore him.”J. Ann Selzer, a pollster who has been a fixture of the Iowa political landscape for three decades, said that in a March survey, likely Democratic caucus voters expressed overwhelming preference for candidates who emphasized a “positive” message. They placed a much greater importance on health care (81 percent of respondents) and climate change (80 percent) than they did impeachment (22 percent).But David Plouffe, Obama’s campaign manager in 2008, argues that while you can ignore Trump, Democrats do need to reckon with what it was about Trump that appealed to his supporters, some of whom voted for him after voting for Obama twice. “I do think there will be a question we will all answer,” Plouffe said. “Are we looking for our version of Trump? Are we looking for the polar opposite? A blend? No matter how you look at this, Trump is a factor in everything.”ImageMayor Pete Buttigieg at a campaign event hosted by the Asian Latino Coalition at the Machinists Hall in Des Moines on April 17.CreditScott Olson/Getty Images“Change the channel,” Pete Buttigieg was telling me a few nights earlier in Minneapolis. “That’s sort of what this is about. There has to be a different feel.” The 37-year-old mayor of South Bend, Ind., was greeting a procession of friends in a basement holding room at the Fine Line Music Café, a downtown nightclub. In about 20 minutes, he would be speaking at a small-donor fund-raiser, for which a crowd of over 400 guests were currently lined up around the block.He was sitting on a couch and jiggling a bottle of water between his right thumb and index finger, clenching it hard enough to leave a large dent in the plastic. He was talking about authenticity, which as a political notion has become an obsession in the Trump years.“Now, interestingly, even though the president is fake in some ways, it is true on another level that what you see is what you get,” Buttigieg said. “And I want to make sure that it’s the one thing I have in common with him.” Robby Mook, Hillary Clinton’s 2016 campaign manager, later told me: “The big idea about Trump was that he was talking plain and telling it like it is, even though he was lying all the time. It was authentic lying.”“I think about this a lot, especially with all these questions about what authenticity means,” Buttigieg continued. “You can think about it too much.” He chuckled. “It’s supposed to be effortless, right?”The echoes of Obama 2008 are unmistakable with Buttigieg. Like Obama in 2008, Buttigieg resists the “I’m a fighter” crutch on which so much Democratic messaging has leaned for decades. “It can be exhausting,” Buttigieg said of this pugilism fixation. He has called it a “fetish.”He urged me not to mistake his aversion to fight-club rhetoric for complacency. “Dr. King was speaking for some of the most marginalized people ever when he said darkness cannot drive out darkness, only light can drive out darkness,” Buttigieg told me. “If anything, when he’s talking about fierceness and urgency and anger, it’s dealing with white liberals who are dragging their feet.” Upstairs, a roomful of white liberals were stomping their feet in the club, chanting, “We want Pete.”They got Pete. He came out to Creedence Clearwater Revival’s “Up Around the Bend,” which seemed like a strange walk-up song until I learned that “the Bend” is apparently what South Bend is sometimes referred to by locals, including its mayor. Buttigieg barely mentioned Trump, except to emphasize that he tries not to talk too much about him. “This president,” Buttigieg said, “like all grotesque things, is hard to look away from.” It’s important to try, he went on. “Because if it’s all about him, it’s not about you.”ImageSenator Elizabeth Warren onstage at a campaign rally in Queens, N.Y., on March 8.CreditDrew Angerer/Getty ImagesElizabeth Warren seems especially proud of her ability to ignore the inescapable — Trump — as a hockey player with a broken leg would be loath to admit pain. “Did I even mention him at all?” the Massachusetts senator asked me following a house party where she spoke in Iowa Falls. I replied that yes, she had in fact mentioned Trump once, in response to a question she received about the special prosecutor Robert Mueller and the Russia investigation. “I got a question,” she told me, suggesting that it didn’t really count.Among the Democratic contenders, Warren is distinguished by the think tank’s worth of policy proposals she has churned out since entering the race, a program she would probably be campaigning on regardless of who currently occupied the White House. Still, Warren’s one riff relating to Trump — she described how she was against impeaching him but changed her mind after reading the Mueller report — elicited the loudest applause in Iowa Falls. Her impeachment call in late April coincided with the start of her recent jump in the polls. Likewise, Warren received a great deal of attention for her refusal to appear on Fox News and for dismissing the network as a “Hate-for-Profit Racket.”Both stances won Warren good will from the party’s liberal base, though spurning Fox was somewhat controversial. To many Democratic strategists, invading Trump’s safe cable space is an underutilized way to provoke the president. “We know that it gets in Trump’s head, and Democrats should be all over that,” Plouffe said, adding that appearing on Fox News could be a centerpiece of any “psy-ops” strategy against Trump. “How do you destabilize this guy? How do you throw him off his game? He is, I think, very vulnerable to that.”In the event of an emergency, as many Democrats view the prospect of a second term for Donald Trump, it’s natural to gravitate to a security blanket, no matter how itchy: Joe Biden, in other words.ImageFormer vice president Joe Biden speaks at a restaurant in Hampton, N.H., on May 13.CreditMichael Dwyer/Associated PressIn the middle of May, the former vice president was making his maiden swing through New Hampshire. His first stop was a pizza bistro in Hampton, lunchtime on a drizzly Monday. A hundred or so bodies were jammed in, seemingly half of them New Hampshire state representatives wearing name-tag pins, many saying they had known the former vice president for years. “Good to see you, man,” Biden said, patting the shoulders of a guy in a Boston Bruins cap near the entrance.Like the Democratic field he leads, Biden’s stump speech, at the multiple rallies where I heard it, was an unruly mess. He name-drops “Barack” a lot. The rest is a familiar-for-him mishmash: several references to his family tragedies, calls for national unity and vows to not to “get down into mud wrestling” with Trump. He had the week before called him a “no-good S.O.B.” and a “clown,” among other things.Biden’s face tends not to move, but you sense furious activity going on behind his eyes. It is as if armies of little chipmunks are working all kinds of levers, reminding him of what notes to hit or people to mention and terms that could now run him afoul of the Woke Police. Mostly, he seems a bit rusty, stepping gingerly into a world of Twitter vigilantes that did not exist the last time he ran for president, in 2008, much less the first time, 20 years earlier, when his campaign was incinerated by a video of his lifting a speech from the British Labor leader Neil Kinnock. Flashes of hesitation crossed his face at the Hampton pizza joint. “My wife, who’s a college professor,” he said, then paused. “A junior-college professor,” he clarified, before clarifying again: “community-college professor.”The safe candidate grabs for safe things — the parable Biden has been telling for years, for instance, which I heard again at a rally that night in Nashua, about how his father used to tell him: “Joey, a job’s about a lot more than a paycheck. It’s about your dignity. It’s about your place in the community, it’s about respect, it’s about being able to look your child in the eye and say, ‘Honey, it’s going to be O.K.’ and mean it.” That basic American promise is dead and needs to be restored, Biden says. The last guy won by promising a return to a mythical America that was once great; why should Biden not promise to make everything O.K. again?If anything, Biden is banking on a lack of faith among Democratic primary voters. Trump’s election left many of them with little confidence that the general electorate could ever look beyond, say, a candidate’s unconventional gender (i.e., female) as they learned the hard way in 2016. “If this was a normal cycle, Joe would not be running,” said Terry Shumaker, a Concord attorney I met at a backyard reception for Biden in Nashua. Shumaker was wearing a “Biden for President” button that he acquired in 1987 and an official pin from when Shumaker served as President Bill Clinton’s ambassador to Trinidad and Tobago. “If not for Trump, he would still be retired,” Shumaker said. “I think he feels called.”It is frequently pointed out that Biden’s propensity for gaffes presents an even greater peril than in previous races, thanks to a vastly less forgiving social media ecosystem. But in New Hampshire, Biden said a few things that could have made mainstream headlines, and I was surprised that they did not. It made me wonder if he would actually benefit from the permission structure that the current president has enabled through his ability to get away with so much. When a woman in the crowd whom Biden called on fumed about Trump that “he is an illegitimate president in my mind,” Biden replied: “Would you be my vice-presidential candidate? Folks, look, I absolutely agree.”Not long ago — five years or so — a former vice president signing on to the idea that the current president is “illegitimate” might have been a rather large deal. In 2019, barely anyone noticed — or they noticed much less than they did a few weeks later when the speaker of the House reportedly said she would like to see the president of the United States in prison.It made me think of something that Marianne Williamson used to talk about when she was running for Congress in 2014, about how things that used to be considered exotic have now been incorporated into the political mainstream. “Today that fringe is baked into the cake,” Williamson told me. She might revile Donald Trump, but she also owed him for this much: In 2020, no candidate, and no idea, can safely be counted out. This is something Williamson could point out from the Democratic debate stage.Mark Leibovich is a staff writer for the magazine and the author of “Big Game: The NFL in Dangerous Times.” He last wrote about the 2020 Republican primary race.