For as long as anyone can remember, the Indiana city of Kokomo has been a conservative stronghold. Ronald Reagan crushed Walter Mondale in Kokomo. Bill Clinton lost twice. So did Barack Obama. The current mayor, a Republican, is running unopposed for re-election. It’s a town known for something it would prefer to forget: a Ku Klux Klan rally in 1923 that was the largest ever.Yet somehow Kokomo produced a union leader whose rhetoric is aimed at toppling the conservative and moneyed classes — a rebel who rejects the niceties of an earlier era in favor of a sharp-edged confrontation.“Billionaires in my opinion don’t have a right to exist,” says Shawn Fain, who is leading the United Automobile Workers in a multifront labor battle against the Big Three carmakers that has little precedent and is making a lot of noise.In interviews, in speeches and on social media, Mr. Fain hammers the wealthy again and again, making the cause of the union’s 150,000 autoworkers at General Motors, Ford Motor and Stellantis something much broader.“There’s a billionaire class, and there’s the rest of us,” he said at an impromptu news conference outside a Ford plant in Wayne, Mich. “We’re all expected to sit back and take the scraps and live paycheck to paycheck and scrape to get by. We’re second-class citizens.”Mr. Fain introduced President Biden on his visit to a U.A.W. picket line last month in Michigan.Pete Marovich for The New York TimesBefore Mr. Fain took over in March, the U.A.W. leadership did not so much scorn the billionaires as strive to emulate them. One executive spent $2 million in embezzled funds on gambling, cocaine and fancy cars. Another bought $13,000 worth of cigars in one day. A federal investigation won 17 convictions against the leadership.Mr. Fain defeated the incumbent by the thinnest of margins. That might have given another candidate an incentive to keep a low profile, secure an adequate contract and declare victory.Not this fellow. He is playing a very high-stakes game.First, there are the aggressive demands and the unusual tactics. The union wants a 40 percent pay raise over four years to make up for much smaller increases in past years, a four-day workweek, annual cost-of-living adjustments, paid health care for retirees and the elimination of a lower pay tier for newer workers. To secure these benefits, the U.A.W. is challenging all three companies at once, which it had never done, by staging a targeted, escalating walkout.Mr. Fain, 54, has made himself the face of the strike, which is in its third week. On Facebook Live in August, he literally threw away a contract proposal from Stellantis, the automaker that absorbed what was once Chrysler. “That’s where it belongs: the trash,” he explained.During a rally with President Biden last week, Mr. Fain invoked President Franklin D. Roosevelt’s hallowed phrase about American factories being the arsenal of democracy. “Today, the enemy isn’t some foreign country miles away — it’s right here in our own area,” he said, casting the automakers in the role of the Axis powers. “It’s corporate greed.”Since U.A.W. members began targeted walkouts over their contract demands, Mr. Fain has made himself the face of the strike.Brittany Greeson for The New York TimesWhether Mr. Fain’s fiery words will lead to effective negotiations is an open question. Fiery words can inspire, but they can also anger. Stellantis said the union leaders seemed “more concerned about pursuing their own political agendas than negotiating.” G.M. denounced the union’s “rhetoric and theatrics,” and Ford said the U.A.W. should focus on talks and not “planning strikes and P.R. events.”“I’m subtle as a hammer,” Mr. Fain acknowledged in an interview. “Probably always was. That’s in my work life. Privately, I’m more shy.” Even his official U.A.W. biography calls him “outspoken” and says he was “ostracized” for his contentious assertions in union meetings.The people who knew him in high school in Kokomo in the 1980s definitely did not see this rise to national prominence coming. They recall an easygoing guy with a lot of respect for authority.“I don’t think Kokomo was a breeding ground for radicals,” said Paul Nicodemus, another member of the class of 1987, adding that the city was “known for having the biggest tree trunk and the largest stuffed bull,” two longtime local tourist attractions. Malcolm X, whom Mr. Fain recently invoked, wasn’t on the curriculum.A closer look, however, reveals how Mr. Fain’s upbringing may have played a role in creating a confrontational figure who vilifies the automakers while alarming Wall Street. “Like watching a slow-moving car crash take place on black ice,” Wedbush analysts wrote as the strike expanded last week to more factories.Mr. Fain’s great-grandparents Gordon and Effie Fain were economic migrants, moving to Kokomo from Kentucky in the 1920s.Mr. Fain’s hometown, Kokomo, Ind., is a traditional Republican bastion.Lee Klafczynski for The New York Times“My grandparents came from poverty,” Mr. Fain said. “When I see people from Mexico or Venezuela being vilified, I see my grandparents. They were born in Kentucky and Tennessee rather than across the border, but I don’t see them as different.”When the Fains arrived, the auto industry in Kokomo was consolidating. In 1937, Chrysler bought a dormant auto plant to make transmissions. Stanley Fain, Shawn’s grandfather, worked for Chrysler for 35 years. Other relatives worked for General Motors.Shawn’s father, Rodger, broke with tradition. He was the Kokomo chief of police; his wife, Stella, was a nurse. In Rodger’s career, there are echoes of his son’s situation. He was hired to clean up a mess.Kokomo had several high-profile murders in the 1970s, making the populace more fearful, but it was also a time when relations between the police and the city were strained. There were allegations that the police were hostage to political whims, which led to a chief’s resignation. The police protested low wages by driving past the mayor’s house with sirens blaring and similar antics, according to a 2014 history of law enforcement in the county. They also went on strike for a day.The first Chrysler pay stub received by Mr. Fain’s grandfather Stanley Fain, a union member, in 1937.Sarah Rice for The New York TimesKokomo has a long automaking history. Chrysler took over a dormant plant in the 1930s and remained the dominant local employer when Mr. Fain was growing up.Lee Klafczynski for The New York TimesRodger Fain, who became chief in 1980, is credited with professionalizing the force and ending the acceptance of gratuities. When the Klan decided to march through town shortly after he took the job, it was a high-tension moment. There were vivid memories of a 1979 march in North Carolina where Klan members shot and killed five participants in a counterdemonstration organized by the Communist Party.The Kokomo march took place without incident, and Chief Fain got credit for an absence of violence. Still, the work wasn’t the sort of thing he wanted his son to do.“My father steered me away from a career in law enforcement,” Mr. Fain said. “When he retired in 1987, he told me that back in his day, you only had to worry about someone pulling a knife. Now everyone was arming themselves.”The 1987 yearbook for Taylor High School had the theme “… lovin’ every minute of it!” There was nothing Shawn loved more than sports. He played basketball all four years of high school. Football, golf, cross-country and baseball took up other seasons.“In Indiana, you have one option, and that’s basketball,” Mr. Fain said. “It was religion. Fathers pushed their sons and even their daughters to play basketball. I had a pretty hard-core basketball coach, in your face all the time, and I adopted a lot of that mentality.”Mr. Fain was an avid athlete in high school, with a particular passion for basketball. In Indiana, “it was religion,” he said.Paul Sancya/Kokomo TribuneThat aggressive attitude on the court served him and the team well, to an extent. The yearbook put a good face on it, calling it an “educational” season, but the record was 5-16.His teammates remember the good parts.“There was one game when we were down by one,” Brian Tate said. “The ball came back to us, I dribbled the length of the court, looked to my right, saw Shawn was open. I said, ‘This is the guy.’ I got it to him, and he nailed it at the last second — game over. He was clutch.”Dr. Tate, now an endodontist, does not recall any budding activists.“We were pretty simple kids,” he said. “I don’t ever remember Shawn by any stretch expressing a political opinion. We never talked about billionaires.”There weren’t many billionaires to talk about. In 1982, Forbes found only 13 when it started listing the country’s richest people. In 1986, there were 26. In 1987, Forbes listed 49.In Kokomo, the non-billionaires were not doing as well. The economy had recovered from the devastating recession of the early 1980s, when one in four workers in the area was unemployed. But it wasn’t moving forward. Local average wages were stagnant, the Labor Department reported.A high school yearbook photo of Mr. Fain, second from right in the back row. “We were pretty simple kids,” a classmate recalled.Lee Klafczynski for The New York Times“Some of them may grow up knowing what they want to do,” Mr. Fain said of teenagers, “but I wasn’t one of them.”Lee Klafczynski for The New York TimesMr. Fain had no idea what to do with his life. “A lot of young teenagers are pushed to pick out a career in the eighth grade, but they haven’t experienced life, they haven’t experienced reality,” he said. “Some of them may grow up knowing what they want to do, but I wasn’t one of them.”He attended the Kokomo branch of Indiana University, not a top-tier basketball school. He got some attention for a good game or two, but dropped out before getting a degree.There were hard times. Mr. Fain married a high school classmate in 1991 and had two girls. “When you go through hardship and are laid off, live on $80-a-week unemployment, apply for government aid to get formula and diapers for your child, it makes you realize what it takes to survive in this world,” he said. (The marriage ended in divorce. He is engaged to Keesha McConaghie, a financial analyst for the U.A.W.)It was a neighbor in the electricians’ union who set Mr. Fain on a viable path. “If you had asked me, ‘Do you want to be an electrician?’ — I probably would have laughed. I knew nothing about that trade. I applied, got in, and the rest is history.” He began working for Chrysler in 1994.His father provided a final element that shaped the future union leader. Rodger Fain ran for the Indiana legislature as a Democrat in 1986. His platform included supporting economic development, attracting high-paying jobs and tearing down the “walls” between labor and management. The vote was close, but as usual Kokomo went for the Republican.Mr. Fain talking to U.A.W. members at a Michigan plant during his run for the union presidency early this year.Jim West/AlamyShawn Fain, raised to be active in the community, ran for the school board in 1998. He wasn’t elected but liked the idea of service.“Some people, when they see things happening they disagree with, let it happen,” Mr. Nicodemus, the former classmate, said. “And there are others like Shawn. Instead of sitting back, he steps up and says, ‘I’ll be the guy.’”That was what happened at the U.A.W., even if for the longest time the union leadership didn’t want the guy.“I didn’t like the way things were going in my plant, was elected, and the rest was history,” Mr. Fain said, who won five terms as a skilled trades committeeman and held other posts.In 2007, he was a leader in a grass-roots campaign to reject a contract with Chrysler that would pay new workers at a lower rate and made other concessions. In accepting the deal, he told U.A.W. leadership, “you might as well get a gun and shoot yourself in the head.”The contract was approved, but Mr. Fain gained a reputation as a rebel. Eleven years ago, he moved from Kokomo to Detroit to work directly for the union. In the ensuing years, corruption scandals at the top of the U.A.W. ended with two successive union presidents in prison, along with a mandate from a court-appointed monitor for the top posts to be elected by popular vote for the first time.It was an opening for reformers, and Mr. Fain led an insurgent ticket that ousted the old guard. He pledged not only to end corruption but also to jettison a go-along, get-along approach that he denounced as “company unionism.” One of his first public acts was to decline the traditional handshake with the automakers at the start of negotiations in July.“I never planned on running for U.A.W. president,” Mr. Fain said. “It wasn’t on my radar. But things change.”Brittany Greeson for The New York TimesHe calls his caustic attitude “a migration,” something he took on “just from experience.” Likewise with his political journey. “I never planned on running for U.A.W. president,” he said. “It wasn’t on my radar. But things change.”The inexorable rise of the billionaires offered more motivation. There are an estimated 750 of them in the United States now, and they are quite a bit richer than they were. “We’re all fed up with seeing the rich get richer,” Mr. Fain declared recently. (His own income last year was $160,000; the U.A.W. lists the president’s base salary at $207,000.)Nelson Lichtenstein, a labor historian, said he saw Mr. Fain as a throwback.“He is using more forceful rhetoric than any U.A.W. leadership in a long while, reaching back to the 1930s and 1940s,” Mr. Lichtenstein said. “The idea of mutual accommodation with the companies is gone.”Mr. Fain took Senator Bernie Sanders, the progressive Vermont independent, to a September rally and cites Walter Reuther, the U.A.W. leader during the postwar years, as an inspiration, along with the Rev. Dr. Martin Luther King Jr. and the “pyramid of success” developed by John Wooden, the coach who produced a U.C.L.A. basketball dynasty. The Wooden principles include at the apex a suggestion about “enjoyment of a difficult challenge.”A strike is a double-edged sword, said Patrick Anderson, chief executive of Anderson Economic Group in East Lansing, Mich. The greater the number of striking workers, the more pressure on the employer. But as the strike goes on, the people who will feel it the worst are those very workers, which gives them an incentive to settle. The automakers know this, of course, which makes for a difficult challenge indeed.Mr. Fain copes with stress by working out and listening to music, cranking up selections from the entire spectrum — hip-hop, ’80s rock, Metallica, Frank Sinatra. He’s still getting used to the job, and to the fact that Shawn Fain from Kokomo Local 1166 is the U.A.W. president.“Surreal,” he calls it. If anything will keep him grounded, he figures it might be this: “U.A.W. leaders in the past tended to forget who they’re here to represent. I don’t forget.” More