DeRay Mckesson, a prominent Black Lives Matter activist and Baltimore native, is entering the Democratic primary for the 2016 Baltimore mayoral race. Here's a look at his role in the movement and his last-minute announcement. (Jenny Starrs/The Washington Post)

DeRay Mckesson, a prominent activist linked to the Black Lives Matter protest movement, filed paperwork Wednesday evening to enter the Democratic primary in the 2016 Baltimore mayoral race.

The activist waited until the final hour before the 9 p.m., Feb. 3, filing deadline to launch the surprise, long-shot bid, which begins just 83 days before voters head to the polls. Because Democrats far outnumber Republicans in the city, Baltimore’s April 26 primary is expected to determine who replaces Mayor Stephanie Rawlings-Blake, the once-rising star in national Democratic politics who announced last year that she would not seek reelection.

“Baltimore is at a moment,” Mckesson, who becomes the first of the prominent post-Ferguson activists to seek public office, said in a phone interview on Wednesday night. “I’m running to usher Baltimore into a new era where our government is accountable to its people and aggressively innovative in how it identifies and solves problems.”

Officials with the city’s Board of Elections confirmed that Mckesson filed his paperwork around 8:50 p.m.

Mckesson, 30, joins a crowded field that includes former mayor Sheila Dixon, who is leading in the polls, state Sen. Catherine Pugh, and city councilmen Carl Stokes and Nick Mosby as well as 10 other Democratic candidates.

The election comes at a time when Baltimore serves as one of the primary anecdotes in the national conversation about the overlay of race, inequality, and inner-city public policy. A poll conducted late last year by The Baltimore Sun found that 58 percent of city primary voters believe the city is “on the wrong track.”

“I’ve lived through too many lofty promises and vague plans,” Mckesson said. “We’ve come to rely on a traditional model of politics only to be rewarded with disappointing results.”

Wielding an online following of hundreds of thousands of people, Mckesson is among the most recognizable of the activists who took to the streets in Ferguson, Mo., and Baltimore in response to killings of unarmed black men by police officers during the last 18 months. A former school administrator in the public schools systems in both Baltimore and Minneapolis, Mckesson joined the protests in Ferguson in late 2014, and later quit his job to become a full-time organizer. Born and raised in Baltimore, he says he moved back to the city full time last March.

Since Ferguson, Mckesson has primarily worked with the groups We the Protesters and Campaign Zero, a policy-oriented arm beneath the broad umbrella of the Black Lives Matter protests that has released research and proposals aimed at increasing police accountability and curbing use of force incidents.

Mckesson’s work and prominence on Twitter has lent the activist considerable influence and a measure of celebrity. He has been among groups of activists courted by the presidential campaigns of Hillary Clinton, Bernie Sanders, and Martin O’Malley, and has met with top officials with the Department of Justice and the White House.

[Why Hillary Clinton and her rivals are struggling to grasp Black Lives Matter]

But the activist and former educator, who has thin ties to the city’s political establishment, enters as a long-shot in the race, which was already the most crowded Democratic mayoral primary since 1999, when then-city councilman Martin O’Malley topped a 15-candidate field.

The most recent public poll in the race, conducted last month, found Dixon in the lead with the support of 27 percent of likely voters polled. The same poll found that 21 percent of respondents were undecided.

“It’s never happened before, someone coming in this late in a race that’s this developed,” Patrick Gonzales, who conducted the January poll, said speaking of a hypothetical last-minute candidate entering the race.

“I can’t imagine that person being successful,” Gonzales said, although he later added that he “wouldn’t completely foreclose” the possibility that a last-minute candidate could catch lightning in a bottle.

Making the decision 

There were apples, pizza, tins of holiday popcorn and freshly brewed coffee spread across the a conference room table inside the Charles Fish Building, a historic storefront once home to a white-owned clothing and furniture store known locally for nondiscriminatory practices toward black customers long before the Civil Rights Movement.

And on a brisk Saturday afternoon in January, a paper sign was taped to the building’s thick glass front door: “DeRay’s meeting: third floor.”

The four-hour policy meeting — attended by a Washington Post reporter on the condition that details of the gathering would not be reported until after Mckesson made his final decision on whether he would enter the race — was a free-for-all, in which a dozen participants reviewed data on education, housing, and criminal justice.

“The question is,” Mckesson asked to the assembled advisers, “what is the world we want to live in? What does that world look like?”

In attendance were Johnetta Elzie and Samuel Sinyangwe, two activists who, with Mckesson, run Campaign Zero (the fourth partner, Brittany Packnett, joined the meeting via conference call); Donnie O’Callaghan, an education policy analyst and Mckesson’s best friend, and several city officials who knew Mckesson from his time working for the school district and his prior nonprofit and community organizing work.

Attendees went line-by-line through the platforms of Dixon and Mosby — at the time the only candidates with published mayoral proposals — with Mckesson marking what the group determined were strengths and weakness of each proposal on large pieces of poster paper taped to the wall.

While Mckesson is best known publicly for his advocacy around criminal justice and policing policy, the bulk of the meeting was spent discussing a host of other issues: education, housing and public health.

“To live in the city we want to live in, everybody has to do their part,” Mckesson said toward the end of the meeting, settling on what will likely be a major theme of his campaign rhetoric.

Mckesson says he is banking on his ability to bring energy, excitement, policy expertise and new ideas to the race. He says he wants to run a different type of campaign — built on the same types of innovative use of technology and deep volunteer networks that have buoyed his activism and criminal justice policy work. But it remains to be seen if status as a relative outsider in Baltimore politics and as an activist will ingratiate him with Baltimore voters or prove a liability.

Mckesson would be the first political outsider elected to the corner office of Baltimore City Hall in modern history. In the last 50 years, voters in Baltimore have only once elected a mayor who was not a sitting city councilor — Kurt Schmoke, the city’s first elected black mayor, who was serving as Baltimore’s State’s Attorney when he was elected in 1987.

Gonzales, who has been polling races in Maryland for 30 years, said that Dixon is beatable, but that the depth of the field of candidates has thus far prevented any of them from consolidating enough support to seriously challenge her.

“One of the challengers is going to have to ignite, and create a little excitement in the city and all of a sudden that one person would be able to go up against Dixon in more of a one-on-one manner.” he said.

“You’d need to successfully pull Dixon off of the perch she’s on — she’s got the biggest base of support,” Gonzales said. “You’ve got to have voters come election day, say ‘we need to try something different.’ If they arrive at that, I cannot imagine that Sheila Dixon is the one they arrive at.”

Who is DeRay Mckesson?

Born in Baltimore to two drug addicts, Mckesson and his sister were raised by his father, who was in and out of treatment, and his great-grandmother.

Mckesson says said he found structure in education — thriving in classes and student government during high school and college at Bowdoin College, where he was elected student body president. After college he took a series of jobs in education, beginning with a two-year stint as a middle school math teacher in Brooklyn through Teach for America. He later moved back to Baltimore to start an after-school, out-of school program for 5th through 8th grade students on the city’s westside before taking jobs as a human resource administrator, first with the Baltimore City Schools and later with the Minneapolis Public Schools.

“DeRay is one of the most intelligent people that I have ever met, certainly wise beyond his years,” said Kim Lewis, who spent six years in the Baltimore City Schools, first as the district’s director of special education and then as its top human resources officer — a capacity in which she hired McKesson as her special assistant. “He knows that when you’re in the business of education, you don’t have any time to waste.”

By the time protests broke out in Ferguson in 2014, Mckesson had moved across the country, and was earning six figures as the Minneapolis district’s top human resources official.

During interviews in Ferguson for some of the first profiles written of him, Mckesson told reporters that his dream was to one day become the deputy mayor of Baltimore — playing up his desire to be a productive member of the team running a major city but playing down his own political ambition.

He briefly moved to St. Louis following the grand jury decision not to indict Officer Darren Wilson for the police shooting of Michael Brown in Ferguson, but returned permanently to Baltimore after the killing of Freddie Gray — which sparked massive protests and riots.

[Ferguson protest organizers: ‘I sleep, eat and breathe this.’]

Armed with a deep Rolodex of media contacts built during the Ferguson protests — there are likely few national reporters or television producers without one of his several cell phone numbers — Mckesson became a go-to interview during the unrest in Baltimore, plastered on cable news as a representative of those who had taken to the streets.

In one of those exchanges, Mckesson grew visibly frustrated with CNN anchor Wolf Blitzer, who spent most of the interview asking the activist, repeatedly, to condemn the riots.

“There’s no excuse for that kind of violence, right?” Blitzer asks Mckesson after listing statistics on the property damage during the rioting.

“There’s no excuse for the seven people that the Baltimore City Police Department has killed in the past year, either, right?” Mckesson, who earlier in the exchange said he hoped to see nothing but peaceful protests, jabbed back.

The exchange — which went on for several more minutes — went viral.

Mckesson surrounds himself with loyal friends and former co-workers, who speak of him and his work in effusive terms. In a New York Times Magazine profile of him and fellow activist Elzie published last May, Jay Caspian Kang noted that “there is a touching earnestness to Mckesson that makes you want to believe everything he says.”

But Mckesson’s popularity has made him a polarizing figure within the ranks of activists, including several who spoke anonymously to Buzzfeed last year in order to trash his leadership style. And his prominence has also earned him scorn from some conservative commentators — many of whom expressed outrage that he was invited by the Yale Divinity School to give a two-day lecture series. A writer for National Review declared him a “next generation race baiter.” Tucker Carlson, the conservative pundit, told a Fox News audience that Mckesson is “not an impressive guy. Just kind of a race hustler.”

But, despite detractors, Mckesson has remained a prominent voice and has attempted to leverage the connections he has built online to the benefit of his activism.  In just the last month he has been interviewed on both the CBS Late Show with Stephen Colbert and The Daily Show with Trevor Noah on Comedy Central.

He first began discussing a the idea of a mayoral run last summer, according to several people close to him, but remained torn on whether he could be viable. In the meantime, he has used his Twitter feed — with more than 292,000 followers, and counting — to send out several trial balloons. In September he sent a seemingly innocuous tweet listing the dates of the primary and general election. The first response from a follower:

“you should run.”

The second response:

“Are you going to run?”

In November, Mckesson dropped his most glaring public hint, bringing up the possibility of a mayoral run seemingly unprompted during an interview with New York magazine.

“Many people have asked me if I’d consider running for mayor of Baltimore,” Mckesson said in the final response of a lengthy a question-and-answer session with Rembert Browne. “I’m confident that protesters will run for office at the local level soon. And do transformative work. And I want to support that. And know protesters would be completely capable.”

By the end of November, Mckesson had begun calling fellow Black Lives Matter activists to survey their feedback on the possibility of a mayoral run. In December, with the support of his closest allies in activism secured, he began floating the idea to various members of the media. But the decision was not made until the final hours, with Mckesson unsure as recently as Wednesday morning if he would turn in the paperwork to be included on the ballot.

At 8:04 p.m. Mckesson texted a Post reporter to say he had finished his paperwork, and was en route to the Board of Elections.