Earlier this year, radio advertisements began airing in and around Charlotte, North Carolina, criticizing the elected sheriff of Mecklenburg County, a Democrat and retired firefighter named Irwin Carmichael. Normally, only the most politically extreme or publicity-hungry sheriffs attract much public notice, and Carmichael was not one of those. “People weren’t even aware of who the sheriff was,” Mark Mellman, a prominent Washington pollster who worked on the race, told me. Carmichael’s office had maintained an agreement with Immigration and Customs Enforcement that deputized his officers to identify undocumented prisoners and turn them over to federal agents, and the radio ads focussed on this issue. “Sheriff Carmichael works with Trump’s deportation force—detaining people for deportation, tearing families apart,” an announcer intoned. “Carmichael’s challengers? They’ve pledged to stop working with Trump’s deportation force.” The anti-Carmichael ads also carried an interesting concluding line—they had been paid for, an announcer said, by the American Civil Liberties Union. Carmichael had gone into his reëlection year looking like a good bet to win. Before the Democratic primary, he had raised more than twice as much money as had his two challengers—a retired homicide detective, Garry McFadden, and a former suburban police chief, Antoine Ensley—combined. But the A.C.L.U. was spending money on the race, too: the radio ads alone matched half of Carmichael’s budget. On primary day, McFadden won, Ensley came in second, and Carmichael finished third. When he spoke to the press after the results came in, the defeated sheriff criticized the “outside forces” that he believed had contributed to his defeat.

For most of its ninety-eight years of existence, the A.C.L.U. has spent its resources largely on litigation, arguing for civil liberties, and against government excess, in the courts. Part of the organization’s DNA is a Bill of Rights purism—the group, always liberal, has famously defended the rights of neo-Nazis and Klansmen to protest—and it has been fastidiously nonpartisan, so prudish about any alliance with political power that its leadership, in the nineteen-eighties and nineties, declined even to give awards to like-minded legislators for fear that it might give the wrong impression. In this midterm year, however, as progressive groups have mushroomed and grown more active, and as liberal billionaires such as Howard Schultz and Tom Steyer have begun to imagine themselves as political heroes and eye Presidential runs, the A.C.L.U., itself newly flush, has begun to move in step with the times. For the first time in its history, the A.C.L.U. is taking an active role in elections. The group has plans to spend more than twenty-five million dollars on races and ballot initiatives by Election Day, in November. Anthony Romero, the group’s executive director, told me, “It used to be that, when I had a referendum I really cared about, I could spend fifty thousand dollars.”

Last year, as a kind of experiment, the A.C.L.U. made a small investment in the district attorney’s race in Philadelphia. The group had become interested in the race because one of the candidates, a former civil-rights lawyer named Larry Krasner, was campaigning on the promise to help end mass incarceration. The A.C.L.U. helped send ex-felons door to door, talking about the brutalities and injustices of prison, and Krasner won. The sheriff’s race in Mecklenburg County was the experiment’s second phase—an investment big enough to help tip a race, spent in an increasingly progressive city in a traditionally conservative state where, the hope was, people could be persuaded to see the mundane brutalities of the local jail anew. The day after the vote in Mecklenburg County, McFadden, who had just won the Democratic nomination, called the A.C.L.U.’s national political director, Faiz Shakir, to thank him. Shakir told me that he encouraged McFadden to make Mecklenburg into a national model for how a progressive sheriff might run his department.

Anthony Romero became the executive director of the A.C.L.U. in 2001, just before the September 11th attacks. The excesses of the Bush Administration’s war on terror, which followed, raised the group’s profile and improved fund-raising. But even that unusual period, Romero told me recently, was not so unusual as this one, because, during the Bush Administration, the civil-liberties cause was mostly a series of lawsuits and editorial arguments, not a movement. After 9/11, when the Bush Administration instituted a program that required visitors from two dozen Muslim-majority countries to register with the government, Romero said, “I don’t remember anyone waving signs that said ‘We are all Muslims.’ ” But last year, when President Trump’s first travel ban targeting Muslims was issued, protests spread at airports around the country, A.C.L.U. lawyers arrived on the scene, and that slogan—“We are all Muslims”—was seen everywhere. Romero had played a small role in helping to organize the Women’s March of 1996, when thirty thousand women and men marched in San Francisco in defense of reproductive rights. That event had required years of centralized planning. After Trump’s election, much larger women’s marches took place in cities around the country, organized in a matter of weeks. The defense of and concern for civil liberties has been central to the resistance to Trump, and the A.C.L.U.’s membership has quadrupled since the President was inaugurated. Romero said that the average age of his membership had dropped by twenty years as a result, and has become somewhat more diverse—“sixteen per cent people of color,” he said. “It’s no longer just college-educated liberals on the coasts.”

Even before this influx of new members, Romero had already begun to think about how the A.C.L.U. might adapt to its current-day political context. In 2013, during the comparative quiet of the late Obama years, Romero had commissioned a study of how the National Rifle Association—another organization built around a specific view of a section of the Bill of Rights—has managed to operate so effectively as a public-advocacy organization. “The big takeaway for me from that study was that they were able to talk about their work not in legalistic policy terms,” Romero said. “On their Web site you won’t find anything about the Second Amendment. It’s all about gun culture.” Romero thought that the A.C.L.U. might do something similar—moving out from the courtrooms and into the work of grassroots mobilization, of policy issues and campaigns. What he wanted, he said, was “to give people a real opportunity to be protagonists.”

Romero was adamant that this plan was within the spirit of the organization—the A.C.L.U.’s first budget, he told me, included a line item for “propaganda,” and the group, in recent years, has worked on grassroots mobilization and numerous ballot initiatives. The main difference, Romero insisted, was the scale. But as the organization deepened its grassroots efforts, in 2017, and then announced the electoral program, at the beginning of this year, Romero understood that the changes would likely rankle a group that he referred to as “the old guard.” In part to reassure this group, Shakir, the national political director, posted an open letter on the A.C.L.U.’s Web site, in January, clarifying that, while “the ACLU plans to do electoral work in a serious way for the first time,” it would not be endorsing candidates, telling its members whom to vote for, or coördinating with any partisan organization.

Within the A.C.L.U.’s orbit, the figure most associated with the “old guard” is Romero’s predecessor, Ira Glasser, who served as the executive director of the organization from 1978 until 2001. The two men had once been close allies—Glasser had first suggested Romero, then an executive with the Ford Foundation, as a candidate to replace him. But the two had fallen out during the Bush Administration, when Romero was challenged by a faction of the A.C.L.U.’s large and famously disputatious board—a fight that Romero won. When I called Glasser, he said that he had been watching the A.C.L.U.’s election plans with mounting alarm. “There is no question that this is a transformative change in the way in which and the principles upon which the A.C.L.U. has operated from its beginning, in 1920,” Glasser said. “I regard this as a departure which has the capacity to destroy the organization as it has always existed.”