DeRay Mckesson was born July 9, 1985, in Baltimore, Maryland. The son of drug addicts, he grew up in Baltimore and was raised by his father and great-grandmother from the age of 3. Politically active as a youth, Mckesson was elected to his school’s student government beginning in the sixth grade.
Mckesson later attended Bowdoin College, a private liberal arts school in Brunswick, Maine. His work as a tour guide at Bowdoin helped persuade many students to attend the college, according to its president, Barry Mills. “There was a whole generation of Bowdoin students who came to the college because of the campus tours DeRay would do,” Mills said in a fawning May 4, 2015 New York Times profile of Mckesson by Jay Caspian Kang. “He’s always known how to inspire a group of people, so it doesn’t surprise me that he’s become a thought leader …”
After graduating from Bowdoin in 2007, Mckesson joined Teach for America, a group that describes itself as a “diverse network of leaders who confront educational inequity by teaching for at least two years and then working with unwavering commitment from every sector of society to create a nation free from this injustice.”
Mckesson taught middle school in New York City for two years before returning to Baltimore to work in the city school system’s human resources department.
Mckesson became politically radicalized by the August 2014 death of Michael Brown, an 18-year-old black criminal who was shot and killed by a white police officer in Ferguson, Missouri during an altercation in which he assaulted the officer and attempted to take away his gun. A friend of Brown subsequently spread the false rumor that the officer had shot Brown while the latter had his hands raised in compliant surrender. Soon thereafter, Mckesson became involved with Black Lives Matter (BLM), a radical Marxist organization claiming that systemic racism pervades not only America’s police departments, but the nation as a whole.
Mckesson articulated his view of the United States as a racist wasteland in a 2015 tweet that said: “Blackness in America is never a question of afraid or unafraid; it’s a matter of varying degrees of fear, as we are victims of state terror.”
Mckesson advocates street violence to advance the BLM cause – and his activism has been generously rewarded in academia. “Looting for me isn’t violent, it’s an expression of anger,” he rationalized while teaching a course titled “Transformational Leadership in the Black Lives Matter Movement” at Yale Divinity School as a teaching fellow in 2015. One day, Mckesson led a class that was discussing “In Defense of Looting,” an essay by Willie Osterweil, whose biography at the New Inquiry website describes him as “a writer, editor, and member of the punk band Vulture Shit.” Among the things Mckesson said in that class were the following:
Mckesson expressed his belief in revolutionary violence during an April 28, 2015 exchange with CNN television personality Wolf Blitzer, glibly dismissing the widespread looting and destruction that sympathetic Democrat authorities had allowed to happen after the recent death in police custody of a black Baltimore man named Freddie Gray. “I think that the unrest, the uprising, whatever you call it, is again a cry for justice here and a cry for justice across the country because police continue to terrorize people,” said Mckesson. “The terrorizing is actually deadly. Broken windows are not broken spines. People are in pain.” Following is a summary of how Mckesson’s discussion with Blitzer unfolded:
Blitzer repeatedly tried to get Mckesson to condemn mob violence, and Mckesson pointedly refused to do so. Asked what his plans in Baltimore were, Mckesson said: “There’s been a lot of positive demonstrations over the past couple months here in Baltimore and across the country because the police have continued to kill people. Tonight will be another night where people come out in the streets to confront a system that is corrupt.”
Blitzer replied, “But you want peaceful protests, right?” Mckesson answered: “Yes, for sure. And remember the people that have been violent since August has been the police. We think about the 300 people that have been killed alone, that is violence. Property damage here that’s been really unfortunate over the past couple, for a day or so here. There have been many days of peaceful protests in Baltimore City and places all around the country.”
Blitzer said, “But at least 15 police officers have been hurt, 200 arrests, 144 vehicle fires, these are statistics, local police have put out 15 structure fires. There is no excuse for that kind of violence, right?” Mckesson replied, “Again, there’s no excuse for the seven people that the Baltimore Police Department has killed in the past year either, right?”
Blitzer insisted, “We’re not making comparisons, obviously,” adding, “We don’t want anybody hurt. I just want to hear you say there should be peaceful protests – not violent protests – in the tradition of Dr. Martin Luther King.” “There should be peaceful protests,” Mckesson said, paying lip service to nonviolence. “I don’t have to condone it to understand it, right, that the pain that people feel is real and you are making a comparison. You are suggesting this idea that broken windows are worse than broken spines, right? And what we know to be true is that the police are killing people everywhere, killing people here, six police officers were involved in the killing of Freddie Gray and we’re looking for justice there. And that’s real, right. Like the violence that the police have been inflicting on communities of color has been sustained and deep.”
Blitzer then said, “But you agree, I assume, with President Obama, who said a few moments ago, there is no excuse for the violence that erupted yesterday, no excuse for the stealing, for the arson. You agree with the president?”
Mckesson responded by saying on the one hand that he personally would advocate peaceful protest, and on the other that mob violence was wholly understandable. “What I agree with is that I advocate people to peacefully protest and know that pain manifests in different ways, and I don’t have to condone it to understand it. People are grieving and people are mourning. And I would advocate personally for people to do it in ways that you are calling ‘peacefully.’ I know that Freddie Gray will never be back, and those windows will be.”
Blitzer pointed out that President Obama had said that the violence “distracted from the peaceful protests and distracted from the mourning that the family of Freddie Gray was seeking yesterday.”
Mckesson replied: “Distracted from progress is when city officials get on TV and call black people in pain ‘thugs,’ right? That’s a distraction. I think that the unrest, the uprising, whatever you call it, is again a cry for justice here and a cry for justice across the country because police continue to terrorize people. The terrorizing is actually deadly.”
President Obama honored Mckesson and other BLM leaders, meeting with them at the White House on February 18, 2016 — a time when Mckesson was engaged in an ill-fated run for mayor of Baltimore. “We had a really strong conversation,” Mckesson said after the event. “We covered so many topics, from policing contracts to use-of-force policies, to Flint and the school-to-prison pipeline, to the upcoming Supreme Court nomination.” “It was important to connect with the president,” Mckesson continued. “I asked about why federal use-of-force policies don’t include policies about preserving life and clear guidelines around de-escalation. The president said he’d look into it.” Following the meeting, Obama praised Mckesson for his “outstanding work mobilizing in Baltimore around these issues.”
In 2015, Mckesson and Brittany Packnett co-founded StayWoke, a BLM outgrowth devoted to protesting against police, restoring the voting rights of formerly incarcerated felons, and opposing the Trump administration.
In the fall of 2016, Mckesson was a fellow at the University of Chicago’s Institute of Politics.
At a September 2016 event sponsored by the San Diego State School of Journalism and Media Studies, Mckesson likened police officers who kill people in the line of duty, to parents who kill their own children. “When is it okay for someone to kill their child?” he said. “That is the only way I can think about this. Somebody’s kid is being killed.” When someone in attendance suggested that police officers undoubtedly face many threatening situations that make them fearful on the job, Mckesson replied: “People in communities are afraid too, and I’m reminded of that every day. People in communities don’t get to just kill people because they’re afraid. Fear doesn’t replace the need for accountability.”
Mckesson’s memoir recounting his activism, On the Other Side of Freedom: The Case for Hope, was published in September 2018 by Viking Press.
On November 2, 2020, the United States Supreme Court ruled, by a 7-1 margin, that Mckesson could not be held civilly liable for an injury that a law-enforcement officer had suffered at a 2016 protest rally led by Mckesson in Baton Rouge, Louisiana. Below are the key facts pertaining to this case:
Mckesson is presently associated with Crooked Media, a political media company founded in 2017 by three men who had served as top staffers in the Obama administration. Mckesson hosts a weekly interview program on Crooked Media’s “Pod Save The People” podcast.
McKesson openly supports reparations for slavery. “Let’s be clear,” he once wrote on Twitter, “reparations is the least that can done to atone for this country’s particularity evil history.”
In 2015 Mckesson was #11 on Fortune‘s “World’s Greatest Leaders” list, and in 2016 he was named one of Time’s “30 Most Influential People on the Internet.” He has been awarded honorary doctorates by The New School (2016) and the Maryland Institute College of Art (2018).
A photograph of Mckesson has been displayed at the Smithsonian National Portrait Gallery.