Quixotic as his campaign might seem, Mckesson still possesses the same seemingly bottomless well of self-confidence that moved him to wake up one morning and drive 550 miles from Minneapolis to Ferguson, Mo., to protest after Michael Brown was shot to death in August 2014. He’s a man who doesn’t much know failure. So all day, in the Ubers he took around the city, between tweets and through interviews, he was personalizing fliers, signing his name in black marker right over the word “education,” covering up the mistake. Then, the plan went, he would pass out these fliers, and then something else would supposedly happen, and then DeRay Mckesson would be the next mayor of Baltimore.

DeRay Mckesson will not be the next mayor of Baltimore.

Baltimore — as anyone who has spent any time there (or just binge-watched “The Wire”) will tell you — is a city with problems. There were 344 murders last year, the most per capita in the city’s history. Its Police Department is being investigated by the Department of Justice over its use of force and possible discriminatory policing. Almost a quarter of its citizens live below the poverty line — many of them in West Baltimore, where hypersegregation pins blacks without the education, or even the public transportation, they would need to escape.

Mckesson, the child of two drug addicts, was raised here by his father and his great-grandmother. His dad eventually got clean and started working 16-hour days at a local seafood distributor, and when Mckesson was in sixth grade, the family moved out of the city to nearby Catonsville. Mckesson was elected to student government from sixth grade all the way through Catonsville High; at Bowdoin College, in Maine, he spent each year as class president, student government president or, in his senior year, both. He majored in government and legal studies but went into education, and soon moved back to Baltimore to work in the city’s public-school system.

By then, he says, he already had mayoral ambitions. “I thought about it a long time ago,” he says. “Then I was No. 2 in human capital in the school system. And it was actually, like, that was the perfect role to get things done.” In 2013, he was recruited to be the senior director of human capital for Minneapolis public schools, and his career path seemed all but mapped out.

Then came Ferguson. Mckesson watched the protests on television and was moved to drive to a town he had never visited, just to bear witness. It was a stark departure from who he was — a self-described “system guy,” a technocrat who believed at his core that the system was good, or at least not inherently bad. “You’re not born woke,” he says. “Something wakes you up.” He was anonymous when he pulled into Ferguson, but in the midst of the tear gas and rubber bullets, he made a small group of friends, including a local woman named Johnetta Elzie. They reported what they saw on social media and eventually started publishing a newsletter. They weren’t organizers, operating more like a communications team. Mckesson was a patient, passionate speaker and an incessant Twitter user. He also understood the power of branding and soon settled on wearing his bright blue vest to every protest.

He had spent much of his life in Baltimore and his entire career in the system, but he was reborn, publicly, in Ferguson. He and Elzie emerged as powerful symbols, new faces of a leaderless movement. By March 2015, he had resigned from his job and become a full-time activist, the biggest star within a movement that had grown, since the 2012 killing of Trayvon Martin, to hold the nation’s attention. Then, in April, Freddie Gray died of a spinal injury suffered in the custody of the Baltimore police, and the protests that followed brought Mckesson home. And in September, Mayor Stephanie Rawlings-Blake announced that she wouldn’t seek re-election in 2016.