She was an intensely driven straight-A student; a church-once-a-week, confession-once-a-month Catholic teen who never used drugs and considered becoming a nun. Even as an adult, she rarely drinks and dabbled in marijuana only twice, calling the experiments a disaster.
A high comes from chanting at a yoga retreat.
On the surface, Annamaria Enenajor was an unlikely candidate to become the face of cannabis legalization reform in Canada.
But as Canada edged towards decriminalizing marijuana, it was frequently Enenajor, as founder and campaign director of Cannabis Amnesty, on the airwaves pushing for the deletion of criminal records for the half-million Canadians with simple possession convictions.
“I think it’s hilarious,” the Toronto criminal defence lawyer says of her leap from strait-laced legal eagle to passionate pot advocate. “I had this joke when I first started Cannabis Amnesty that marijuana was as significant in my life as oregano, an herb I thought about occasionally and didn’t really use.”
As incongruous as it might initially appear, Enenajor’s path makes perfect sense. A zeal for social justice, combined with a determined focus to confront systemic racism, weaves through her life and a career arc that finds her now, at only 34, a partner in one of Toronto’s high-profile law firms and an emerging champion of legal reform.
That passion to give voice to the often voiceless was evident when she was part of a team representing prisoners at Rikers Island in a civil-rights class action against New York City to end the use of excessive force. It was evident when, also in New York, she represented LGBT asylum-seekers, and staffed a legal clinic for Hispanic immigrants in the Bronx. And when she volunteered at a New Delhi human rights documentation centre, monitoring refugees in India.
And it drives her work on the cannabis project. The government has proposed pardoningthose with convictions, technically called a record suspension, but those records would still exist. Enenajor continues to rally support to have those lingering files completely expunged.
“Having come from a critical social science background which I tried to apply in law school, I had a strong understanding of how drug prosecutions in general were disproportionately meted out against vulnerable members of society, Indigenous people, people of colour, people with addictions,” she explains.
“That’s been sort of what drew me to criminal law as well. The fact that our criminal justice system tends to put away those people who are the most vulnerable, not necessarily those who are the worst members of society.”
That sensitivity in her approach to the law is what prompted the powerhouse boutique firm headed by Clayton Ruby and Brian Shiller to name Enenajor a partner last year. She was only 33 and had been with the firm since 2015.
“It is incredibly young,” acknowledges Ruby. “But she’s got the qualities we want; not just excellence and skills — I mean she clerked for the present Chief Justice of Canada — but mostly that sense of commitment to change. Somewhere along the line, she decided she was not going to just do great lawyering, because she can go down to the corporate world and make a lot more money doing it. She decided she really wanted to make the world a better place. That’s what makes her appropriate for us.”
While that might sound Pollyannaish, Enenajor’s compassionate approach not only peppers her resumé, it is evident in her voice. As she reflects on her career, sitting in her office on the second floor of a repurposed Victorian house on Isabella St., her words sometimes crack with emotion. That tremor is there when she recalls the concentration of “Black men in cages” in the New York penal system and it surfaces again when discussing the “devastating mental health implications” that overzealous policing and detention have on the marginalized.
That humanistic perspective can be traced back to her youth and the influence of her parents.
The daughter of a Black Nigerian father and a white Slovak mother, Enenajor moved from Slovakia to Edmonton when she was 6. There, her mother studied Slavic linguistics but when her student visa expired two years later, the family relocated to Nigeria.
Enenajor says her father, Gilbert, a doctor, had been active in student organizations, and on his return he started a hospital and tried to bring improved medical care to poor communities.
Annamaria’s mother, Anna, was a religious woman who put a strong emphasis on the “preferential option for the poor” principle, which stresses ensuring the well-being of society’s downtrodden and powerless.
Enenajor inherited the sympathetic tendencies of both.
“I was a very strong Catholic until probably about my mid-20s and then as I drifted away, the accoutrements and rituals of the church disappeared but that sense of justice and the beatitudes — like blessed are the poor, the weak and the humble — always stayed with me,” she says.
“The highest aspiration as a human is to serve others and to do so with love. There’s this great quote from (philosopher) Dr. Cornel West and he says ‘Never forget that justice is what love looks like in public.’ ”
When Annamaria was 10, the family moved back to Canada, settling in the Don Mills and Sheppard area of Toronto, a neighbourhood she recalls as a “happy bubble of multiculturalism.”
While her mother first worked teaching high school equivalency courses at the Mimico Correctional Centre, her dad spent his early days mostly at the Fairview Library. Gilbert had been a pediatrician in Nigeria and he was studying to be a licensed physician in Canada. Annamaria was often at his side doing her homework and surrounded by books that brought the world to her. Even as a preteen Gilbert recalls his daughter taking an interest in international affairs, politics and religion. She also had the un-childlike ability to sit and read for hours.
“She was a very inquisitive child,” Gilbert recalls.
Gilbert says he and Anna tried to shelter their three children from racism so they would “grow up to love everybody” and view everyone as equal, but even the cocoon of family life isn’t a completely protective bubble wrap.
“When she started to see how (some minorities) were treated, she said there’s no way you can say there’s no racism.”
Seeing discrimination, Gilbert believes, planted the desire in his daughter “to defend things that are not right.”
Annamaria remembers being bullied her in Edmonton school where she and her sister “were pretty much the only Black kids, and when I say Black, we’re half-Black.”
She thought it remarkably shallow that someone would judge another based solely on the pigment of their skin.
“That really instilled in me how devastating racism can be because it diminishes your sense of self-worth,” she says. “When you have a diminished sense of self-worth, there is no need for you to be a contributing member of society. So that’s what has always stood out to me as being incredibly toxic about racism.”
Once the family was in Toronto, Enenajor came to understand, even as a high schooler, that visible minorities were treated more harshly by institutions such as the police; she inherently understood she was subject to different expectations. It informed her behaviour.
“I would not touch drugs at all because I knew that if I were to make that mistake it would follow me for the rest of my life,” she says. “I had internalized this knowledge that I would be scrutinized more by the police or by authorities than my peers who were not of a minority background.”
A Toronto Star investigation in 2017 revealed that Black people with no criminal convictions were three times more likely to be arrested for marijuana possession than white people. Consumption rates tend to be the same between the two groups.
Enenajor immersed herself in schoolwork with a drive much like that of her parents. Her dad ultimately did become a Canadian doctor while her mom progressed to be a school administrator.
Upon graduation from St. Joseph’s Morrow Park Catholic Secondary School, Enenajor earned a prestigious $100,000 Loran Scholarship, from a foundation supporting Canada’s future leaders. Even with that, she considered devoting herself to religious works as a nun.
“She said, ‘I just feel I want to go help people. I want to go and feed refugees,’” recalls Gilbert. Neither parent was pleased with this apparent change in plan.
“There was an intervention,” says Enenajor
Enenajor went to school and put together the resumé of a classic overachiever.
Enenajor aced everything she studied, graduating from the University of Toronto as the top student in international relations, which she had mixed with courses in Christianity and culture. Then she earned a Master’s degree in forced migration from the Refugee Studies Centre at the University of Oxford. That took her to New Delhi as a volunteer monitoring the rights of refugees.
Then her rapid progress hit a speed bump.
Enenajor returned to Canada to study law at McGill University and, for the first time, she struggled with the subject matter. She met an academic counsellor and was told “law school isn’t for everyone.”
An angry Enenajor adopted an I’ll-show-you attitude.
“I was always a very, very serious student. My parents instilled that in me,” she says. “Education is very important. It’s how you get yourself out of poverty. It’s how you make a name for yourself. It’s how you ensure your income. It’s how you participate in society. You have to become educated. No one can take that away from you.”
She ultimately graduated with civil and common law degrees and was awarded the David L. Johnson gold medal for highly distinguished standing while contributing to the academic, social and community life at the school in an outstanding manner. She served as vice-president of the Black Law Students’ Association of McGill, as a legal researcher at the McGill International Criminal Justice Clinic and she volunteered off campus as a math tutor in low-income neighbourhoods.
In 2012, she was hired to be a law clerk with the Supreme Court of Canada.
“She had this concern for fairness,” recalls Richard Wagner, now the chief justice, of the woman he calls “one of my best clerks.”
“Every time I would talk to her about any issues, not only the legal issues in our files but other social issues, you could sense that she had this sensitivity. She was sensitive to the human condition and to do the right thing and the fair thing.”
While it was her fascination with the O.J. Simpson trial as an 11-year-old that first gave her the idea that a law career might be an interesting life, it was her work on behalf of the Rikers Island inmates, after that Supreme Court experience, that pushed her to become a criminal defence attorney.
During her work at the massive New York firm Ropes & Gray, she was exposed to one of America’s notorious prison complexes. She catalogued the use-of-force incidents and she was stunned by how coldly the suffering was recounted in the records, even if a prisoner had been beaten so badly he lost an eye or suffered hearing loss. She was also troubled that there were men lingering in jail who hadn’t been convicted.
“It was almost like these aren’t humans,” she says.
Enenajor says their treatment made her despair.
“We pride ourselves as a western civilization as being progressive, and we have humans in chains for having done something that doesn’t warrant it. I thought it was so shameful, I felt I had to so something about it.
“It’s the prison system that turned me on to criminal defence because the stakes are so high.”
Enenajor maintained a busy pro bono practice in New York, which helped develop her skills. She loved the firm but yearned for something more.
“Should I spend the rest of my life making sure this billionaire gets enough millions from this billionaire?”
Enenajor took a “substantial pay cut” to return to Toronto, signing on with what is now Ruby Shiller Enenajor DiGiuseppe. She says both Ruby and Shiller encourage her to speak publicly about legal issues that concern her, particularly when the perspective of a woman or person of colour is missing.
While she’s been spending about 30 per cent of her time on the cannabis file, her day planner is full of the typical cases undertaken by a defence attorney: sex assaults, obstruction of a peace officer, assault with a weapon, living off the avails of prostitution, attempted murder. She anticipates being in court for a murder trial in February.
She concedes that most of her life is consumed by work but she does periodically get away to the Bahamas to attend a holistic yoga retreat. She is hoping to go for an entire month sometime soon.
“I keep saying I’m trying to change that (work/life balance) but it just never happens. I keep saying next month, I’ll work out more and I’ll try to go out more.”
Single, Enenajor lives on the top floor of her family’s home, moving in after she found living alone in a downtown apartment “just horrible mentally.”
Almost each workday, she has lunch at a restaurant with Ruby, akin to having her own personal Yoda.
“I always come with questions about my cases and say, look, this is what I’m dealing with, this is the kind of strategy I want to use. What do you think of this theory of the case? What do you think of this line of reasoning? This case law?
“They are always fantastic ideas I get from him … That’s why I don’t make a big stink about the fact I’ve gained 20 pounds since coming.”
Enenajor struggled with anxiety in law school and early in her career — fighting off doubts that she was good enough — but weekly therapy sessions have helped keep it “very well managed.” So does intense preparation before a court appearance.
“I can’t remember the last time it manifested itself,” she says.
Cannabis, even legal, is not something she’ll use to help with the issue.
“I’m into mindfulness meditation,” she says. “So I try not to take mind-altering substances.”
She has tried CBD, the non-psychoactive cannabis compound that some use for anxiety control and other medical benefits. Enenajor found it had little impact. As for marijuana containing THC, the ingredient that causes a high, she tried it twice and lost interest.
The first was during law school. She’d been surprised as she moved through her post-secondary education at how casual drug use was among students from wealthier backgrounds and how they showed no fear of begin stopped by police, frisked and arrested. It was a different world from her teenage years. Enenajor, a non-smoker, gave it a whirl, had difficulty inhaling and found “it did nothing.”
The second time was a few years ago on a visit to the Bob Marley Museum in Jamaica when the tour guide told her the property was covered by a constitutional exemption.
“I went with the flow. I took a brownie,” she recalls. Like the first time, she noticed no impact.
“So I took another one. An hour later, pfff,” she says, blowing air through her lips. “It was a terrible experience. It was just like the feeling of being very drunk, like being too drunk. You start feeling anxious (with) poor memory, poor co-ordination. Thank goodness I was there with my partner at the time and he was able to take care of me.”
Although she’s not finished with the cannabis file, Enenajor’s extra-curricular work will also focus on both prison reform and trying to improve the criminal justice system, particularly from the perspective of race.
“There’s systematic racism and historical injustices that play into outcomes that we still need to acknowledge,” she says, noting that “a lot of my experience in criminal justice has seen how law amplifies inequalities in many ways and is a disservice to people. It is an impediment to them improving their lot in life and it’s an impediment to them getting the kind of help they need.”
Enenajor feels there is an appetite for change and “a space for someone like myself to make those kinds of arguments and to make them in a compelling way to bring about reform.”
Enenajor recently sat on a panel at a Toronto region judges conference to speak on how to apply social context in the sentencing of African-Canadian offenders.
“One of the factors that a judge should take into consideration in sentencing a person is moral blameworthiness,” she says. “How morally blameworthy is an individual who has their choices limited by life’s circumstances?
“It was very well received. I was happy.”
As for prison reform, federal Public Safety Minister Ralph Goodale recently drafted Bill C-83 that the government says would effectively, eliminate solitary confinement. While it is progress, Enenajor questions why many prisoners are incarcerated at all.
“I think we overuse prisons,” she says. “I would call myself a prison abolitionist because I think that we structure our system as if the logical outcome of every case where there’s a guilty finding is prison. I think it should be structured as a last resort for people who are the most dangerous and need to be separated from society.”
She finds it particularly reprehensible that people with addictions or mental illness end up behind bars.
Enenajor says that while she was growing up, her value and self-worth were constantly reinforced by her parents and her teachers so she understood what she could go on to accomplish in life “had nothing to do with my background or skin colour. It’s all about who I am as a person.”
But she came to understand that some people of colour “are unable to do that because they’ve internalized that hatred that society has, those stereotypes and those doubts that society puts on you.”
That can sometimes lead to low self-esteem and choices that can, in turn, lead to involvement with the criminal system.
She believes all Canadians have an obligation to act when they see the system isn’t working for some.
Enenajor’s rapid ascent to partner — something she notes is easier in a small firm — has strengthened the potential for her to a leader in this belief.
When Enenajor became a partner at Ruby Shiller, she was so thrilled, she took a photo of the masthead with her name on it and sent it to her parents. She couldn’t help herself.
“It’s beyond my wildest dreams that I’m a partner,” she says.
“I’ve gone through incredibly stressful periods and worked with clients whose lives are on the line, and there have been difficult ethical decisions I’ve had to make and horror stories. None of that stress can compare to the stress of having the feeling that I was not doing what I was put on this earth to do. Being able to find that is such an incredible blessing.”