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On Twitter, in media interviews, on panels and in his book, Jamil Jivani, pictured here in Oshawa, Ontario, on July 15, 2020, has derided Black Lives Matter as anti-family fringe race activists, cast skepticism on the term 'systemic racism' and says only a minority of loud voices on Twitter support the movement to defund the police.Carlos Osorio/The Globe and Mail

Jamil Jivani tends to start his own story with how he was a young Black man who fared poorly in high school but then, counter to expectation, bootstrapped his way to law school at Yale University. He uses this anecdote in his book, interviews and speeches.

At a recent press conference, Mr. Jivani, the province’s advocate for community opportunities, told the story again.

“I stand before you today as a person who was streamed by the public school system in this province as a teenager. I was put into applied courses,” he said, flanked by Ontario’s Premier and Education Minister, who had just announced the province would eliminate academic streaming in Grade 9 and most suspensions for young students.

“I know that very few people who experience streaming in our schools ever make it to a place like this: standing at an official podium alongside the Premier of Ontario.”

Ontario to end academic streaming that splits students into applied, academic tracks

The news was seen as a win for equity in education, but many couldn’t square Mr. Jivani as the face of this announcement with what he tweeted later that day:

“We need an investigation into the billion dollar hip-hop industry, concerning why so many rappers are killed,” he wrote. “[It] incentivizes young dudes to lean into these gangster images in order to make quick money and fame. Stop making excuses, hold hip-hop accountable.”

Many had come to see Mr. Jivani as an important advocate who had spent years on campaigns to empower Black communities and address problems in policing. Some were still with him, but to others, this felt like a betrayal. At a time of racial reckoning, when the Black Lives Matter movement and calls to defund the police have gained wider appeal, many couldn’t understand why Mr. Jivani was using his new platform and increased profile to criticize the very people he was supposed to uplift.

On Twitter, in media interviews, on panels and in his book, he has derided Black Lives Matter as anti-family fringe race activists, cast skepticism on the term “systemic racism” and says only a minority of loud voices on Twitter support the movement to defund the police.

“You thought, here’s a guy who’s going to be a real heavyweight for the community in terms of carrying our issues forward, really knocking down barriers for the youth that so many of us work with,” said Neil Price, a Black educator at Humber College who was once friends with Mr. Jivani and worked alongside him on projects related to police reform. “It’s almost like a fairytale turned into a nightmare.”

Mr. Jivani, 32, is clean shaven and bald. He has the kind of eyebrows that help emphasize a point and the disarming smile of a youth pastor. He often wears blazers on top of logo tees.

He and his two sisters were raised by their Scottish-Irish mother in Brampton after their father, a Kenyan immigrant, left when Mr. Jivani was in elementary school. Growing up with a disappointing and then absent father played a large role in shaping his outlook on life.

“It defined my relationship with the outside world in a certain way,” he said in an interview this week. “I was very desperately trying to find male role models and examples to look up to.”

He studied at Humber College for a year and then went to York University, where he excelled, which paved the path to Yale law school.

On this path, Mr. Jivani found plenty of the role models he was seeking. Mr. Price, who met him in 2013 when both completed the same fellowship, describes Mr. Jivani as a master networker. He scored a coveted position interning at Torys, the prestigious Bay Street law firm and while there developed a relationship with the dean of York’s Osgoode Hall, which led to teaching job at the law school the following year while doing activist work on the side.

He launched a campaign called Jane and Finch Votes to increase participation in the 2015 federal election in the northwest Toronto neighbourhood with a large Black population, at one point giving away Thanksgiving turkeys to motivate residents. Osgoode Hall put out a press release praising the endeavour and the campaign was covered in the local press.

Butterfly GoPaul, a resident of the neighbourhood and long-time community activist who has seen how engaged her neighbours are on politics, bristled at Mr. Jivani’s efforts, which she found patronizing and self-serving.

“He came into this community trying to educate [us] around elections but not talking about how this community has organized in different ways,” she said.

Though his law practice ended in 2015 when he finished his placement with Torys, that year Mr. Jivani was awarded Young Lawyer of the Year from the Canadian Association of Black Lawyers.

Andray Domise, a contributing editor for Maclean’s, says he first saw Mr. Jivani speak at a community panel in 2014 on policing and thought, “This is a pretty smart brother.” He was addressing the same topics many Black progressives were, including the need to eliminate carding.

After that, Black Lives Matter Toronto rose to prominence and Mr. Domise noticed Mr. Jivani constantly attacking its members.

“Within a couple of years, his tenor had changed so much,” he said. Mr. Jivani was no longer speaking to Black people about knowing their rights, Mr. Domise said, but to white people about the moral failings of Black culture.

In 2018, Mr. Jivani published Why Young Men, which garnered praise as a breakthrough work of social science and was long-listed for the Toronto Book Award.

In it, Mr. Jivani explores jihadi radicalization, fatherlessness and “gangster culture.” He writes about being tempted by a life of crime but ultimately choosing the virtuous path that led him to Yale.

Around the time of the book’s release, Mr. Jivani was diagnosed with Stage IV non-Hodgkin lymphoma and spent that year and part of 2019 undergoing treatment – he is now in remission.

During that period of recovery, aside from book promotions, he stepped back from community work but toward religion, joining Kingdom House Christian Centre, a Brampton church with a predominantly Black congregation, which he says changed his life “dramatically.”

He said the timing was “in God’s hands” when, last summer, members of Mr. Ford’s team reached out to him saying they had read his book and wanted to chat. He delivered a presentation on themes from the book that could be addressed by government policy and, after a series of meetings, in December he was appointed to the position of advocate for community opportunities – a $500 per day gig (to a maximum of $72,000 per year) that will last until March, 2022.

Mr. Domise, a vocal critic of Mr. Ford who ran against his late brother, Rob Ford, in the 2014 municipal election, viewed the appointment with pessimism.

“There’s a tendency that conservative politicians have to try to find a Black person that repeats their innermost thoughts, the thoughts that they can’t say out loud,” he said.

Mr. Jivani’s scorn for Black Lives Matter, he says, is one such example.

A few weeks ago, Mr. Jivani tweeted, “... Black Lives Matter is actually short for ‘Black lives matter only if they’re killed by cops so don’t ask us about gangs and also we hate the nuclear family and capitalism but don’t ask about that either.’ ”

The Premier declined a request for an interview but Ivana Yelich, his spokesperson, wrote in an e-mail, “By engaging directly with young people, especially those from disadvantaged communities, Jamil is helping ensure the government is providing the support they need to succeed and reach their true potential.”

Warren Salmon, president of the Ontario Alliance of Black School Educators, first connected with Mr. Jivani earlier this year when he and a few others sent an e-mail to the Education Minister with suggestions on how to address anti-Black racism, including eliminating streaming. They copied many others on the e-mail, including the Prime Minister, several MPs and Mr. Jivani – who was the first (and one of the only) to respond. He met with the group, heard their suggestions and then a few months later came the destreaming announcement.

Mr. Salmon was impressed. “He actually walked the talk,” he said.

That Mr. Jivani’s “heart is in the right place” makes his more inflammatory positions easier to tolerate, Mr. Salmon said. “We’re not going to agree on everything.”

But Akwasi Owusu-Bempah, an assistant professor at the University of Toronto who studies race and policing, said the takeaway when reading Mr. Jivani’s writing is individuals are to blame if they can’t bootstrap their way to success the way Mr. Jivani did, which lets governments off the hook.

“He’s made his way into more and more offices and rooms and positions based on this piece of work that in many ways certainly wouldn’t pass the academic peer-review process,” he said.

While the Ford government may have drawn inspiration from the book, Mr. Jivani’s characterization of Black masculinity in it was “deeply troubling” to Rinaldo Walcott, a Black studies scholar and former director of University of Toronto’s Women & Gender Studies Institute.

“It ties into long, historical stereotypes of Black men as worthless, as irresponsible,” he said.

The dangers of having Mr. Jivani in this role is that “significant, important policy positions will be obscured,” he said.

In an interview, Mr. Jivani agreed with his critics that poverty, lack of opportunity and inadequate social services made youth vulnerable to gang culture and criminality, but he said those who oppose him are “very ideological in their views, meaning they really want to boil every problem down into this kind of ideological fit. Like, ‘It’s all about poverty.’ ”

The Globe and Mail reached out to several of Mr. Jivani’s early supporters for comment for this story: people he described as his mentors, those who had championed his book or worked alongside him. They either did not respond or declined to comment on the record, citing disagreements with recent comments Mr. Jivani has made, and a desire to distance themselves from the controversy around him.

Mr. Jivani can’t understand why people dismiss all his work or characterize him as anti-Black because they disagree with some of his views.

“I’m the same guy who just fought for six months to get streaming and suspensions ended, because I understand that that’s an unfairness that young Black men face,” he said. “One doesn’t cross out the other. I can work on that issue and also say that hip hop is a problem.”

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