David Freedlander writes about politics and culture. He lives in New York.

RYE, N.H.—The August air at dusk has a slight chill to it, as Julián Castro stands on a back porch on New Hampshire’s seacoast. He runs through a blistering version of his stump speech, promising to rejoin the Paris Climate Accords, reform immigration laws, tax inherited wealth and raise wages, and—and here he slows down a bit, taking his time to set a scene he knows his audience is desperate for. He explains how, on his first day on the job, with all the press cameras shuttering away and the helicopter doors open on the White House lawn, he is going to slap the former President Donald Trump and Melania Trump on the back and say to them, as he ushers them to the waiting choppers, “¡Adiós!”

The audience laughs and cheers and there is time for one more question, and it is the big one: How are you going to beat Trump?


Just as Castro begins to answer, an airplane, landing at nearby Manchester airport, flies low over the party. No one can hear anything over the plane’s growling engines. But Castro keeps talking, smiling, jabbing the air in front of him, uttering words only he understands or can hear.

This should be Julián Castro’s moment. At a time when issues of immigration and family separation, race and the border are front and center in the national consciousness, the story of a third-generation Mexican-American would seem tailor-made to resonate emotionally with voters. His great-grandfather was a coffin maker who died in the Mexican revolution, and his great-grandmother was lying on her deathbed when their daughter, Castro’s grandmother, was taken along with her sister across the border by distant relatives. As she used to tell Julián, the sisters were just waved past by border guards with rifles who spoke to her in a language she didn’t understand, her guardian dragging the little girls along. Once settled in San Antonio, the girls were separated between two different families, and Castro’s grandmother struggled with depression throughout her life, wailing well into her old age that they “wouldn’t let me say goodbye!”

And yet, as he spoke to Democratic voters in New Hampshire, Castro’s campaign seemed to be on the cusp of ending. Despite being pegged as the future of the Democratic Party almost as soon as he arrived on the scene as San Antonio mayor in 2009, and as the “Latino Obama” after he delivered a memorable keynote to the 2012 Democratic National Convention, here he was, stuck in the third tier of a sprawling field, polling around the 1 percent mark. And most crucially, he had not yet qualified for the third Democratic debate in September, which required polling at 2 percent to make it on the stage.

“So if you get a strange phone call, maybe from an unlisted number in the next couple of days, please answer it,” Castro told his audience to laughs.

But no matter how good of a candidate you are, it is hard to be heard these days. Not when the reality TV show president has commandeered the nation’s attention. Not when there are nearly two dozen candidates, most of whom have nearly identical policy ideas and similarly solid résumés. Even Latinos, who by all accounts should be rallying behind the path-breaking grandson of a Mexican-American immigrant, have been slow to respond to Castro’s message.

Julián Castro campaigns in New Hampshire, hoping to garner enough support to make the next Democratic debate and become the party's nominee for president. This is his sixth trip to New Hampshire since launching his candidacy in January. He speaks to a crowd of about a hundred people in a Bedford backyard. | Melissa Lyttle for Politico Magazine

Finally, he hears the crowd and he starts over. He goes through the mechanics of winning back the 80,000 or so Rust Belt voters who swung the election to Trump in 2016, turning out voters in the urban core and in the suburbs. He mentions Orange County, California, a onetime Republican stronghold, as a place that recently flipped blue, boosted by a population that is 30 percent Latino and a majority nonwhite. He talked about flipping Arizona, and bringing home the grand prize: Texas, and its 38 electoral votes.

“We are right there. We are this close to make or break point in the campaign,” Castro told me after the event. At one point when he was an undergraduate at Stanford, Castro and his twin brother, Joaquin, explored careers in local television news. Even today, the presidential hopeful can sound like a political pundit when he talks about his race. “Everything is on the line right now. I think we can make it to the September debate. If we can’t, the deadline for October is coming up, so we are going to do everything we can to make that. The future of the campaign is going to happen over the next few weeks.”

Castro is an heir to Obama, having served as secretary of Housing and Urban Development from 2014 to 2017. He is young, just 44 at a time when many in the party are looking for a new generation. He is a policy wonk, a former mayor who can speak as fluently about zoning, gentrification and housing affordability at a time when those issues have risen to the fore among the party’s young and urban base.

On a casual day filled with backyard gatherings and picnics at parks, Julián Castro's national press secretary, Sawyer Hackett, wears a t-shirt that's a crowd favorite. | Melissa Lyttle for Politico Magazine

And yet here he is, struggling to be heard over the drone of a Delta jet, trying to make his case.

“I mean, obviously,” he says, “I wish I were doing better than 1 percent.”



***

Castro made the debate stage a day after his weekend in New Hampshire, when some 20 people out of 1,001 respondents in a CNN poll selected him as their first choice for president. To hear Castro’s campaign tell it, that is an achievement that they don’t receive nearly enough credit for. Castro is one of the top 10 candidates standing after beginning the 2020 campaign with no real email list, no campaign funds banked, no early state staffers or deep-pocketed benefactors or anything resembling a campaign infrastructure.

If Castro had any sort of moment in this presidential campaign, of the kind that candidates are constantly trying to create, it was in the first debate in July, when he left Beto O’Rourke sputtering over immigration policy, because unlike Castro, O’Rourke did not favor eliminating a section of immigration law known as Section 1325 that criminalizes illegal entry.

Melissa Lyttle for Politico Magazine

The move was bold, and shrewd, because it showed how out-front Castro has been on policy issues. And not just on immigration, where his call to decriminalize illegal border crossing was soon copied by most of the rest of the field (much to the dismay of party elders who could already see the “Democrats Favor Open Borders” ads coming from the Republicans in the fall.) Castro has also put forward a comprehensive housing program that would allow renters to deduct a portion of their rent in the same way homeowners can deduct a portion of their mortgage; an education plan that eliminates tuition for public colleges and ties student debt repayment to graduates’ income; a criminal justice reform proposal that ends qualified immunity; not to mention comprehensive plans on animal rights, taxes and curbing white nationalism.

And yet Elizabeth Warren is the “policy candidate.” And Pete Buttigieg, seven years younger than Castro, is the Millennial Mayor candidate. Joe Biden is the one with better ties to the Obama administration. And even though Castro proposes taxing inheritances of $2 million or more, raising the capital gains tax rate, providing a $3,000 per child tax credit, paid family and medical leave and a $15 nationwide minimum wage, Bernie Sanders is the candidate known for fighting income inequality. And somehow, despite being able to trace his lineage to the American colonies of the 18th century, Beto O’Rourke, a son of El Paso and fluent in Spanish, has become the candidate of immigration and the new Texas.

That, and the fact that both the national media and the party’s progressive wing had begun to tire of O’Rourke’s schtick, made him an inviting target for any candidate looking to make a name for themselves. But when Castro went after O’Rourke in the debate, it was the first time any of the candidates had targeted any other onstage.

“I knew we were going to address immigration, and I thought we would have a point of difference,” said Castro, who had spent weeks before the first debate looking at late-night YouTube videos of Democratic presidential primary debates going back to 1988. “I think of it like Tom Brady looking at game film,” he said. “I had that ready just in case.”

The reviews of Castro’s were good and should have garnered him a second look from voters and a polling bump. But they didn’t. For whatever reason, the path-breaking Latino candidate with an easy command of the intricacies of immigration policy didn’t see his numbers improve, especially after his call to decriminalize border crossing was copied by much of the rest of the field. The incident echoed, in some respects, his near-miss with the Clinton campaign in 2016.

Top: Adelino Vellis, 10, holds a sign up for Julián Castro as he listens to him speak in a Bedford backyard. Vellis, a twin who is one minute older than his brother, just like Castro, loves history and politics and has seen several of the candidates speak this year, including Elizabeth Warren, who spoke in his own backyard. Bottom Left: A little girl wears a Julián Castro sticker on her shirt at the Hillsborough County Democrats Picnic in Greenfield. Bottom Right: Castro was one of about half a dozen candidates to swing by the Hillsborough County Democrats Picnic in Greenfield. | Melissa Lyttle for Politico Magazine

Castro was on the shortlist to run with Hillary Clinton in 2016, but was passed over in favor of Tim Kaine when the campaign figured that, thanks to Trump’s rhetoric, there wouldn’t be much of a need to boost Hispanic turnout.

People close to the Clinton campaign’s deliberations say Castro wasn’t considered as much as the press was led to believe, that it was probably always going to be a boring white guy all along, and that then Labor Secretary Tom Perez probably would have been a more likely choice had they wanted to go with a Latino. Castro was already receiving criticism during the veepstakes. Progressives thought he was insufficiently tough on Wall Street when he ran HUD, and they dinged him for violating the Hatch Act by praising Clinton in an interview he gave as secretary; the charge sounds almost quaint now.

Although Castro had been considering a statewide run in Texas for years, probably for governor, before O’Rourke’s 2018 run against Ted Cruz it was widely thought that the state wasn’t ready to elect a Democrat yet. After losing the veepstakes, he had planned to remain in Washington, angle for a job in the Hillary Clinton administration, possibly as secretary of Education or Transportation or in the Office of Management and Budget, or at some politically influential think tank.

Instead he moved back to San Antonio in 2017 and signaled his interest in running for president almost immediately. He started a PAC, Opportunity First, which raised a half-million dollars and supported “young, progressive leaders” around the country. He wrote a pre-campaign memoir, An Unlikely Journey: Waking Up From My American Dream, which details his rise from the barrios of West San Antonio through Stanford, Harvard Law, San Antonio’s political scene and to the Obama administration, with his twin, Joaquin, younger by one minute, with him all the way.

Top: Julián Castro was one of about half a dozen candidates to swing by the Hillsborough County Democrats Picnic in Greenfield, NH Sunday afternoon. After speaking at the Hillsborough County Democrats Picnic and taking questions from the press, Castro takes selfies with supporters in the crowd and talks to children. Bottom: Homeowner Ronnie Werner says a few words to Castro after he spoke to a hundred or so people gathered in her backyard in Rye. | Melissa Lyttle for Politico Magazine

But other than the book and the PAC, Castro really wasn’t a major figure in the “Invisible Primary” period after the 2016 election. He wasn’t a regular on “Pod Save America,” there weren’t glossy magazine profiles or stories of him stumping for down-ballot candidates in the early primary states. It is hard to go from Housing secretary to presidential front-runner, and much harder when you are last seen in the public eye as being not picked for your party’s presidential ticket. It is telling that few of the most sought-after political operatives in Democratic circles rushed to join Castro’s campaign even though he had signaled he was in the race for a long time. Instead of veterans of the Obama and Clinton or Sanders campaigns, the Castro team is filled with many longtime loyalists from San Antonio and his Housing secretary days.

The most likely and most obvious political path for Castro would be to consolidate the Latino vote, a population which comprises an increasingly growing share of the population but one that, frustratingly for Democratic strategists, doesn’t vote in nearly the numbers that it could. Latinos are the now the largest minority group in the country and account for about 10 percent to 20 percent of the Democratic Party electorate. 2020 polling on Latinos is scant, but the polling that does exist shows that immigration isn’t the big concern among Latinos that many analysts assume it to be. Jobs and health care rank above immigration, and polling shows that Latinos tend to favor the candidates who are preferred by the rest of the Democratic electorate like Warren, Sanders and Biden. A recent open-ended Pew survey put Castro below even Buttigieg in a poll of Latino Democrats.

Melissa Lyttle for Politico Magazine

As Castro sees it, white pundits and political analysts are underestimating what it would mean for turnout if the first Latino were on the ticket. A lot is made about how Cuban-Americans don’t vote like Puerto Ricans who don’t vote like Central Americans who don’t necessarily respond to a third-generation Mexican-American with occasionally shaky Spanish. Castro says those differences will melt though once a nominee actually comes from the Latino community, and he suspects that even Republican-leaning Hispanic voters will support a path to victory that, he told the audience in New Hampshire that evening, would give the Democrats Florida, Arizona, and at last, the great state of Texas.

Hillary Clinton did slightly worse among Latinos compared to Barack Obama, even with Trump’s anti-immigration rhetoric firing up nativists. Part of Castro’s pitch as a nominee is that he would change that calculus, that seeing one of their own onstage would mean that the quarter or so of the Latino electorate that now supports Trump would come his way in big numbers. But the fact that has not occurred yet—that even Latino voters in the Democratic primary aren’t rushing to Castro’s cause—isn’t a good sign for his theory of the case. Nevada, the third in the nation caucus state has among the highest Hispanic populations in the country, a state where Hispanics account for roughly 30 percent of the vote. In five polls of the state conducted so far this year, however, Castro has failed to best 1 percent.



***

Castro’s story is a remarkable one. His grandmother, the one who walked across the border as a child, remained troubled by the experience for most of her life, living under the care of her strict guardians, and later, their children. At 32, she had a daughter with an 18-year-old from the neighborhood, who disappeared soon after—local lore had it that he joined the military—and when he returned, refused to acknowledge that the child was his. That child was the Castros’ mother, known as Rosie, who as a little girl went with her mother to clean the houses of San Antonio’s well-to-do. She bristled against the discipline of her mother’s caretakers, against the class inequalities that she saw on their rounds, and, as a young woman, got swept up in heady rush of Chicano activism in Texas in the '60s and '70s.

The Castros’ father, Jesse Guzman, was married with five kids of his own when he met Rosie. The two never married, and the relationship fell apart, but the boys' memory of childhood is of smoky, beer-soaked organizing meetings for groups like La Raza Unida party, a Chicano nationalist organization that tried to become a national third party in the early '70s, and the Committee for Barrio Betterment, which fought for more resources and political representation for Hispanics in San Antonio, and on whose line Rosie Castro ran and lost a race for the City Council.

It is hard not to see the Castro brothers, and Julián in particular, as a buttoned down, analytically detached and establishmentarian reaction to their free-spirit mother. “They were just more serious and sophisticated in their understanding of politics than I had ever confronted in a 19- or 20-year-old,” said Luis Fraga, a political scientist who advised Julián on his thesis titled, “Strategies of Coalition Building in a Multi-Racial City,” at Stanford, where Julián kept a map on his dorm room wall of the San Antonio council district he would later represent. “I don’t mean sitting down and scheming. I just mean a political maturity you don’t often see.”

Castro stopped by the Cross Roads House, a transitional housing shelter in Portsmouth, where he met with housing advocates to discuss homelessness and housing issues, after a tour of the facilities. During a meet & greet, he recorded a brief video for one man to send to a friend. | Melissa Lyttle for Politico Magazine

Rosie Castro, by contrast, once told The New York Times Magazine, in a profile of Julián soon after he was elected mayor of San Antonio, that the Alamo, that symbol of American courage and (of course) a major tourist draw to the city, was a place where the heroes “were a bunch of drunks and crooks and slaveholding imperialists who conquered land that didn’t belong to them,” adding, “I can truly say that I hate that place and everything it stands for.”

(The campaign declined a request to make Rosie available for an interview.)

It was Luis Fraga, Castro’s mentor, who gave Castro the political philosophy that would be his guiding principle, what Fraga called in a book, the “informed public interest.”

It means, Fraga told me, that you can propose a policy that benefits one group, and others will come to support it if they see that it benefits them as well. A better immigration system will help immigrants and those who wish to immigrate, in other words, but it will shore up the Social Security trust fund and boost the economy too.

“We need to find a way in this country for people to be able to see that immigrants are not their enemies,” Castro said, noting that somehow in places with the highest rates of immigration inflow are often the most tolerant, places like big urban centers and even along the border in places like Texas and Arizona.

“People need to be able to reality test,” he said. “If you have a phobia in psychology, like if you are afraid of elevators, there are two ways to deal with it. One of them is that we put you on an elevator and send you right up to the 80th floor. The other is that you go in gradually. Maybe you go in and the doors stay open and the elevator doesn’t go anywhere. Then the doors close. Then you take a ride up to one floor, and so on and so forth. I get it if you live in some of these communities that have been lily white and suddenly there are a lot of Hispanics and you say, ‘Hey, what is going on here?’ But we need to show people that the glass is half full instead of half empty.

“My brother has this line that I wish I had thought of, that if you think it’s bad that all of these people want to come here, imagine how it would be if no one wanted to come here.”

The Castros were minor civic celebrities by the time they returned to San Antonio from law school, and Castro was elected to the City Council the next year, at 26 becoming the youngest City Council member in San Antonio’s history. Four years later, he ran for mayor and was defeated by Phil Hardberger, a retired judge 40 years older than Castro, who had made much of both the Castros’ remarkable youth and the fact that Julián had seemed to pass off his brother as himself at the San Antonio River Parade he was unable to attend. “If you’re 18 years old and having a date, it might be a youthful prank when you swap out your brother. But when you’re running for mayor of a city with 1.3 million people and sending in your brother as an impersonator, I do see a problem with it,” he told reporters. (The Castros said it was all a misunderstanding: Joaquin was unable to correct the parade M.C. as he was introduced over the roar of the crowd repeatedly as Julián; the whole episode made them minor celebrities as the episode was picked up by the national media.)

Castro wipes the sweat off his brow and holds an ice cold Topo Chico offered to him by the homeowners after a meet & greet in a Bedford backyard. | Melissa Lyttle for Politico Magazine

Castro, who had told his wife on their first date that he would one day be mayor of San Antonio, thought he was done with politics after the loss. But four years later he ran again, poaching senior staff from Hardberger’s campaign, including his treasurer, Mike Beldon, the owner of a local roofing company and a prominent civic leader.

“He has calmed down a lot since he was on the council,” Beldon said. “Julián is a pretty introverted guy. He has had to overcome his basic shyness. He doesn’t do the abrazo, you know, ‘the embrace,’ very easily.”

***

At the first-floor restaurant of Castro’s Manchester hotel, he orders an iced tea that he mixes with water and sugar, and then water and sugar again, to get the ratio just right. A waitress comes by and loudly makes a show of offering him a straw even though she “technically” isn’t supposed to, believing that she has a customer who shares her disdain of liberal overreach.

“This is why [Trump campaign manager Brad] Parscale and all of them are doing that,” he said, referring to the Trump campaign’s efforts to make a show of the left’s efforts to curb plastic straw usage.

Trump, Castro says, is like an athlete with only one move: “It’s like James Harden’s backstep, or Manny Pacquiao with his move to the side. He is just very good mechanically in interviews, in just subsuming whatever it is journalists are after. Journalists thrive on that gotcha moment, and he is getting over on it all the time. It’s why, he told Lester Holt, he fired Comey. It takes the sting out. He’s like a fastball pitcher. You see what he does and it is easy to predict the future.”

As Castro sees it, the midterms, which saw Democrats gain 40 seats and grab control of the House, gave a candidate like him an opening. Secured of at least a foothold in the power structure, Democrats could take a second look at a different kind of candidate.

“The midterms were a relief valve. I never believed I would be the most fiery, burn-it-all-down kind of candidate,” he said. “After 2018, I figured people would start to consider different personalities and approaches to the race.”

But if it is hard to picture Castro railing against the millionaires and billionaires, or leading the crowd in a chant for “Big, structural change!” he has been one of the more aggressive and strategic candidates in the race. It’s not just taking on Beto over immigration in the debate; Castro also, in his first campaign trip, traveled to Puerto Rico. The day he announced his candidacy, he also announced that even the campaign’s interns would be paid $15 an hour, and he encouraged them to unionize. He recently cut an ad that aired on only one station and in one location—on Fox News in Bedminster, New Jersey, when Trump was vacationing at his club— in which he openly blamed Trump for the mass shooting in El Paso.

“As we saw in El Paso, Americans were killed because you stoked the fire of racists,” Castro said in the spot. “Innocent people were shot down because they look different from you. Because they look like me. They look like my family.”

Castro told me the ad was designed to garner the free media that would come along with such a move. It was inspired, he said, by all of the people who go on Fox knowing they are speaking directly with the president. The ad coincided with a similar stunt from Joaquin, who came up with the idea of tweeting out the names and employers of some of Trump’s biggest donors in San Antonio, a move that led Republicans to claim he was jeopardizing their safety. It was Joaquin’s move, but Julián quickly endorsed the plan and refused to back away from it.

The paradox of Castro’s campaign is that, as with his stance on decriminalizing the border, he has had an impact on the larger field but he hasn’t reaped the benefit. Now, he finds himself once again in a position where he needs to land a big punch.

After speaking in the backyard of a house in Rye, answering every question and posing for every picture, Castro sits down in an empty chair after the crowd leaves. | Melissa Lyttle for Politico Magazine

“The boys were always so much more reserved than Rosie,” said Dr. Laura Barberena, a San Antonio-based political consultant who worked on Joaquin’s first campaign and went on to work on both the Bill Clinton and Obama campaigns. “She is an activist—nobody can talk over her, and nobody wants to mess with her, and the boys were never much risk takers, but you see Julián now, and you really see the Rosie coming out of him. It’s like he has figured that if ever he was going to start taking risks it would be now, when he has nothing left to lose.”

Castro’s campaign says that the notion of a specific and personal Lone Star rivalry with O’Rourke is overstated. The Castros campaigned for O’Rourke in his 2018 Senate run. But it is hard not to see how Castro would be doing better without O’Rourke in the race. Still, the Castro camp rolls their eyes at the media’s onetime infatuation with O’Rourke as a candidate, and at some of O’Rourke’s antics, most recently his latest campaign reset in the wake of the El Paso shootings. It is the kind of cushion given to Texas Anglos from privileged backgrounds, not to third-generation Chicanos.

“I’ve tried my entire life to make the most out of this first chance that I had,” Castro recently told the Texas Tribune. “Most people who came from where I came from didn’t necessarily get a second chance.”

If 2018 meant that some of the oxygen for a fiery nominee was released into the atmosphere, it also, Castro says, gave Democrats pause over what kind of candidate could beat Trump.

“The way 2016 came down, hardly anybody expected it. It blindsided a lot of Democrats and so you have people that are wondering if something like that could happen again. But caution isn’t always the best strategy,” he said. “When Democrats win it is with a new coalition of people, whether it is Kennedy being the first Catholic, or Jimmy Carter coming up through the South or Barack Obama’s diverse young coalition of voters. There is more evidence that you should throw caution to the wind instead of driving right into that fear. I know in some ways I am not the safest choice.”

But around a sprawling backyard with a swimming pool in the town of Cornish, New Hampshire, after Castro finished up his bit about saying “¡Adiós!” to the Trumps on the White House lawn, Mauricio Vivaldo, a 59-year-old retired educator and immigrant from Bolivia said that he was dismayed that more Latinos had not attended Castro’s events.

“There are a lot of Latin people in Manchester, a lot in Nashua. They know he is running but they are not here to support him,” Vivaldo said. He said he thought the local Latino community would come out in a big way for Castro if he were the nominee, but for now they aren’t sold.

“Getting a Latin person in the White House would be great, but you can’t forget everything else. Right now, I am just looking. We need someone who is going to beat Trump. And I am not optimistic.”