Annamaria Enenajor

2Thank you very much.

4Uh-oh.

6I, I don't know what kind of question, how I'm supposed to answer that kind of question.

8I mean, I, I, I feel myself very fortunate to surround myself with people that I'm constantly learning from. And so the thought of positioning myself as being more intelligent than others is First of all, I find it not productive because there's always something that you can learn. There's always not even just facts but skills. And I love that idea of absorbing the gifts of others and learning from them. So like I've, I have found my existence in law to be quite joyful because of that constant journey of exploration. And you think you've mastered something and you come across someone who just does it so much better. Or who does it more effectively or more compassionately.

9And so I, I think what's more valuable is what we can teach each other, and to recognize that you're always learning. And if you think of yourself as being static in terms of skill, in terms of knowledge in terms of your ability to advocate, If you are satisfied with your skill level, I think you will quickly be outpaced by those who are hungrier than you, by those who are more ambitious than you, by those who are more humble in seeing how their skills can be constantly amplified, renewed, refreshed. And so I like that path. I like that journey. There's nothing static about the skill of practicing law and practicing litigation.

10And if I were to label myself as somebody who is smart relative to others, I think that's actually a dangerous path to go down because it means that I'm not constantly pushing myself, which is, I think, part of the reason for my success.

12Yes, yes.

14Yes, well, it's I think it's a little bit richer than just opposing government. I think it's about Ensuring the proper checks and balances exist on the government to preserve and protect our democracy and the individual rights of the people who are subject to the government's monopoly on the use of force against its citizens. Liberty, dignity, the right to life, the right to freedom, all of those things I think are at the core of the passion that I have for this profession and for the line of the profession that I've chosen to pursue. But I would say that I see passion in commercial litigators as well. Like, I see passion in at least maybe the ones that, you know, I work with and where there's crossover in our files.

15But I see them, they're passionate about the truth. They're passionate about their client's predicament. It may not be the sort of meta lofty goals and principles that are are sort of always brought to the forefront in criminal litigation where it's such a stark, where the sort of opposition that exists between individual rights and the state are so stark and quite upfront. But I do find that there are commercial litigators that I've encountered that I work with. My partner, Brian Shiller, does commercial and civil litigation, and I see him being passionate about fighting for the underdog, even in commercial disputes, about fighting for the truth, about not letting slimy, swindly corrupt business people get the best of people who are honest and have integrity and who fill our marketplace with good ideas and with good products or with just the commercial everyday reality that we all rely on.

16We rely on the certainty of contracts. We rely You know, that people will be held responsible for costs that they bring to others. So I think that sometimes there's this temptation to create a stark contrast between the kind of work that public and criminal lawyers do and the kind of work that commercial litigators do. But as I, you know, work more and more with commercial litigators and civil litigators in that field, I find that our values often align with the truth-seeking function that is at core of an adversarial system of litigation.

18Absolutely. And in fact, they're constitutionally required to do so. One of the things that I find, as you mentioned at the outset of our interview, I worked in New York for a few years before moving back to Canada. And I'm— I must say that I find that the Canadian justice system and the Canadian Crowns generally that I've encountered really abide by the principle in a Supreme Court of Canada case called Boucher that has dictated that, you know, the role of the Crown is not to seek conviction. It's to exercise their function in the public interest. It's a truth-seeking function. It's not about winning or losing. It's about making sure to preserve the integrity of the justice system, the values of the Charters, and the truth-seeking function of the court.

19And I have found that as a result of that, the Crown counsel that I've worked with in many cases are a lot more reasonable and less prosecutorial-minded than the attorneys, the district attorneys, the US attorneys that I sat across the table from in the United States. And I find that the underlying principle of the function of the Crown is to serve the public interest. And I think part of the way that that manifests itself is that In my trial strategy, when I first get a client's case, my primary objective is to persuade the Crown that it is not in the public interest to proceed with these charges. And I'm oftentimes successful. And it's because the Crown is not seeking a conviction willy-nilly.

20I find that the Crown attorneys that I've worked with take very seriously their role as public officers and take very seriously their role to ensure that an innocent person isn't convicted as well. So, and I know that there are always going to be exceptions and there are always going to be, you know, horror stories and there's always going to be abuse of discretion. That's, we're human. But I find generally the culture that I find, it supports the idea that even in the Crown's office, there are lofty goals relating to ensuring that justice is always done.

23law clients and their clients.

26That's a really good question. I think, I think for the most part, society, it does receive its information about what goes on in courts and what the function of the various justice system participants is from, or the various, you know, functions are from the media. And so it's the media's focus that directs their understanding of these cases. And often the media is driven by stories that are more sensational, and they are driven by personality and character. And a lot of the leading lights in the criminal defense bar, like Marie Henein, like my former partner Clayton Ruby, have very strong personalities and characters, which translates into very attractive profile for people to examine and sort of be curious about.

27Like, I remember in the I remember early on in the Ghomeshi when Jian Ghomeshi was arrested and then it was learned, it became news that he was going to be defended by Marie Henein and everybody wanted to know like, who is this Lindem? And there was a lot of stories about the firm website and the, the style of photography and the sort of people call— people were, were making reference to the fact that, you know, it was very branded it was different than any other website. And crowns just don't have websites that, you know, market themselves like that. So it's— there's just not that much fodder for commentary.

28And, and also I think generally crown offices discourage public statements made by individual crowns whereas defence lawyers often use the court of public opinion to bolster their client's case or their impression. And they're often open to making commentary after a case has been decided either in their favour or against, you know, on the steps of the courthouse. And that's something we see less of, and it's actually, I think, quite discouraged from in Crown offices. But I do think that there is a role to play in educating the public about the important function that both the Crown and the defence have and to do so in a responsible way. So, and that's part of the reason that, or one of the things that I try to do when I go on television programs and speak to the state of certain areas of law is to provide that balanced approach because there's an important function to both sides.

30I did, yes.

32Oh, really?

34Where did you study?

36Oh, cool.

38Yeah, I actually— it was a double major, International Relations and Christianity and Culture.

40Yeah, so absolutely. So I grew up in quite a religious background, like a family. I— and the religion specifically was Catholicism. So my, my mom is Catholic and she raised us Catholic, and so I went to Catholic school my whole life. It was all I knew. I went to Catholic high school, and then I went to St. Mike's at University of Toronto. And I was always a very questioning individual. I always wanted to learn more and to ground everything that I did in knowledge. And so when I got to my adult years, I started asking myself, like, what is this Christianity that I— this Catholicism that I that, that informs my worldview, that it's the way that I see the world because it's— that's how I was raised.

41And the University of Toronto at St. Michael's College had this interesting program which was Christianity and Culture, which wasn't precisely a theological program, so The difference between the study of theology and the study of religion is that religion is sort of an objective study of a religious phenomenon out there in the world. So it doesn't come from a position of belief, whereas theology, which is the, the form of study where that actually underpins a lot of seminary work. So if you are training to become a priest or a nun or a monk or something in a lot of different traditions, a theological education is the education is an understanding that comes from a desire to grow deeper in your faith, in your, you know, religious beliefs.

42So it's not sort of an objective study of a phenomenon out there. It is as a Christian, what am I doing with XYZ? And the program at St. Michael's College was more towards the religious studies. So growing up in Catholic schools, I, you know, was learning religion, but it was from people who were religious and who believed in it, right? So there's some questions that you couldn't ask. Whereas if you're learning a religion, someone who is— who does not believe in it at all could still study it and understand it and learn about it and have interesting insights into it. And so I I entered the Christianity and Culture program because I wanted to understand the development of this phenomenon called Christianity that has influenced so much of modern human history and to just become more informed about the, the beautiful aspects of it and the ugly aspects of it as well.

43And so it was a really interesting program that allowed me to do that. And I enjoyed the courses immensely and the faculty were, were wonderful and very open-minded and intellectually curious. And like, I took courses like, you know, the like Theology and Science, and where I wrote a paper on like the theological implications of like extraterrestrial life. And and then studied also, you know about the history of Christian missionaries in, in Asia and how unsuccessful they were in some countries and how, how successful they were in others. And, and why, as a sociological phenomenon and a political phenomenon, why that happened. So it was very, it was very interesting for me because it cast what I had, what I had grown up with in a different light.

45I think it, I think it did. I think one of the things that was always very central to me and in my personal faith journey was the sense of justice and social justice. And I had always looked up to, you know, individuals that were heralded as important in the Catholic Church like Archbishop Oscar Romero, who was a fighter for social justice and for the, for the rights of the poor in Latin America. And so that I think those ideas had always been in my mind, this notion that faith must be acted upon and it must inform justice for all. And there are a lot of values that I think my faith instilled in me.

46Then I have to say that as I transitioned out of, you know, young adulthood into, into like later adulthood.

48Mature. Yeah, mature. Old age. No. Decrepitiveness.

50Let's call it optimal condition. Thank you. Thank you. I fell out of faith with I fell out of belief with the, with the, with Catholicism and with the church. And there were just certain principles that, and ideas and troubling aspects of the belief system, or aspects of the belief system that troubled me that I couldn't get behind. And, you know, I'm not the kind of person that will say, oh, you know what, I'll just take 60% and the 40% I'll just ignore. Like, if it's not If it— if I have trouble with like, I have trouble with the church, deep trouble with the church's position on homosexuality, deep trouble with the church's position on, on women in positions of leadership.

51Like, there's all of these— there's a laundry list of things that I find troubling and I could not in good conscience continue to to be a part of that faith system. But I still think that there are a lot of values that stuck with me and that inform my desire— like, inform and motivate me to do the work that I do.

53Yeah, absolutely. I think the older I got, the more I started to question things and and ask why in relation to things that I took for granted. And, and also just the— I felt like there was— that I didn't require it anymore to hold up the values that I cherish, that I can, I can do that in my life, independent of affiliation with a church.

55Honestly, I think it's just the people around me. The— like, I I really owe a lot to, to my mentor Clayton Ruby who was not religious at all And yet I feel like just as one, as an adult, as a person that I encountered in my life, had one of the strongest moral compasses. And it just came from his strong sense of an internal commitment to justice and equality. And, you know, even just something as simple as the Golden Rule, do unto others as you would like them to do unto you, which is is not tied to any religious specific religious affiliation, but is present in different forms in many of them.

56And it's the notion that you know, why would you hurt another person? Why would you let another person suffer? If you were in that position, you would want someone to help you. You would want someone to stand up for you. You wouldn't want to be treated differently. And I, I feel very strongly about that. And it doesn't have to be linked to any religion or specific philosophy, but it gives my life a deep sense of meaning to know that I'm working to help other people. And I'm also a big fan of psychologist, philosopher Viktor E. Frankl, who wrote a book, Man's Search for Meaning. And it was his— he's a Holocaust survivor and he wrote about what got him through the darkest days in concentration camps.

57And, and he, he spoke about and he developed a philosophy about that. At the core of human survival and existence and joy in life is this eternal search for meaning. What, what gives you meaning? What gives you hope? And I think I've, I found that in my work. I found that in my relationships. I found that in my marriage. I found that in my children. Like, I, when I think about what I'm doing and what I hope to do, what I'm trying to do for the justice system, I think about if any of my kids were ever in front of the justice system, like, what would I want that system to be for them?

58I want it to be, you know, fair judges. I want it to be compassionate and understanding and creative prosecutors. And I want it to be fierce defense counsel who will fight for them no matter what. So that's kind of what I'm what I'm trying to, to, to build, and that's how I find meaning. And I don't, I don't need— I find that I don't need religion to do that.

61Oh yeah, but, but I think in the, in the last few years it has become more common. And the reason is because we have a growing body of social science evidence that is telling us what we need to do in order to actually prevent crimes. And it's not to build bigger jails and it's not to create more lethal police forces. Prevention of crimes, and this is something that I'm actually quite passionate about, and I've worked with the Criminal Lawyers Association to advocate for. The root cause of crimes is poverty, social dysfunction, addiction, mental health, marginalization. And I think it's very complicated because we assume that crime is largely the result of the moral failing of an individual.

62And there are some individuals, particularly those with extraordinary power who abuse that power against people who are vulnerable, who it is a moral failing on their part. They have chosen to do something that is wrong. And I am glad that we have a justice system that can be responsive to that. I don't want to— I don't want to live in a society where those people feel that there is impunity for their actions. But I also don't want to live in a justice system at the other end of the spectrum or live in a country where we have a justice system that exists on the other end of the spectrum, where the focus is on using the criminal justice system to solve problems that are not criminal justice problems by nature.

63So if we look at addiction to drugs and mental health issues, if those are treated for what they are, those individuals will not end up in the justice system. And that's part of the reason why, in addition to doing my litigation work, I also do a lot of public advocacy work. Like I founded Cannabis Amnesty, which was an organization that sought to, that actually successfully lobbied the governments to implement a regime of record expungement or record sequestration for all individuals with simple cannabis possession. On their records, an offense that's no longer a crime. And these are people who, because that action resulted in a charge and resulted in conviction, those people have faced extraordinary challenges in reintegrating back into society and putting that criminal past behind them.

64And that seems counterproductive to the kind of holistically sound society that we want to live in. So I think Like, I'm very, I'm deeply interested. I often testify in front of House and Senate committees for justice and human rights about issues relating to new pieces of legislation that are coming up because I think it's so important that we understand that we cannot use criminal laws to solve not criminal problems, to solve problems that are social, economic, you know, historical trauma, mental health-based problems. We should not be using the criminal justice system to do that. And we've had so many studies and reports right now that show that we are and we do continue to do that.

65If we look at the over-incarceration of Indigenous people in the criminal justice system, a lot of the actions that result in the interactions with the law, the root cause of those interactions with the law, with those antisocial behaviors, is the intergenerational trauma that people in Indigenous communities have experienced at the hands of the Canadian government. So it is important for us to recognize that and to not, to understand that there is a spectrum of moral blameworthiness and responsibility that individuals have when it comes to their own actions. And some people who are victims of the system have no choice but to behave in a certain way to soothe their trauma and anguish in a certain way through drugs, through alcohol.

66And that ultimately leads to more self-destructive behavior, including criminal behavior. So if we understand that crime is is a socially complex phenomenon, I think we're better placed to solve it. I don't think you'll find any criminal defense lawyer saying, we love crime. I'm

68Maybe, perhaps. But I feel like the—

70I

72But you know what?

74Yeah, well, some of them. And then there's the legal aid problem as well, but that's for another discussion. But I think it's, it's, we understand how complex this is

76we often come from communities and backgrounds where we have seen the criminal justice system being used improperly to solve problems.

78That's right.

80Yes. So while I was working in New York, I worked for a wonderful firm, Ropes& Gray. They were very— just like a very thoughtful firm. Everybody that worked there was so conscientious and smart and really good mentors for me. I had a few good mentors and some people I still keep in touch with, and I just didn't find the subject matter of the work to be that fulfilling. And I'm, as you can probably gauge from our last, you know, half an hour of conversations, like, I don't like being unsatisfied. I have to continually push for the optimum, optimal solution. Yeah, optimal condition. Exactly. So I, the firm that I was at had a great, a really strong pro bono program, various different organizations and encouraged their associates to participate in these pro bono programs because it was one of the ways that associates who were junior could get in-court experience, sort of on-the-feet experience, because the multimillion-dollar files are staffed with a lot more lawyers, and you're the most junior, you will almost never see the inside of a courtroom.

81Although I did, because I had a wonderful mentor. But the pro bono program afforded me an opportunity to get involved and to take on more responsibility and to gain more skills in litigation. And one of the cases that I was working on was a class action lawsuit against New York City Department of Corrections for abuse of prisoners on Rikers Island. And, and yeah, and, and I worked very closely with the lead lawyer, lead lawyers on that file. And it was through that work that I became more educated about criminal justice. You know, I had taken crim in law school and not been, and worked on some crim as well as at the Supreme Court of Canada, but it wasn't really until I was shocked and taken aback and felt like this was something that I had to do, that I had to be a part of in fighting because there was so much inherent unfairness.

82And at the same time, so this was around, as you mentioned, 2013 to 2015, Stephen Harper was still Prime Minister of Canada and he had passed a few years earlier a number of tough-on-crime policies that were very reminiscent of all of the pro, like of the anti-crime and tough on crime policies of the United States that we were now seeing the failure of while I was in the US. So like things like the three-strike rules, mandatory minimums, all of those things. And I was inspired by the work of criminal defense lawyers like Clayton Ruby, like his partners at the time, Gerald Chan and Nader Hassan, who were fighting against these laws, who brought constitutional challenges, who fought for their clients and who were saying, look, I don't care I don't care if you are the Prime Minister of Canada.

83What you are doing is wrong. It violates the Constitution and it violates my client's rights. And I was so inspired by that.

85I know.

87I know. I know. I often think that. I said, because I remember just sitting in my office and just reading. I was, you know, like, you take a break from work and you're just reading the news and you're scrolling down and you're like, oh, hell no, I gotta come home and do something about this. So I reached out, one of my co-clerks knew Gerald Chan and I reached out to him by email and we had, I visited, I traveled back to Toronto over a few weekends and visited them and interviewed with them and met them. And they said, we'd be happy to have you join our firm, and the rest is history.

89So he is one of the most extraordinarily generous emotionally intelligent, and compassionate and morally righteous people that I've ever met. He was drawn to criminal law because he was drawn to assisting the underdog. He, I think, is an— was an inherently subversive person who was driven by his own moral compass, and he always believed strongly and firmly in the equality of all. Unwaveringly, he fought for the rights of gay and lesbian women in the army. He fought for equality for women, and it was always at the forefront of his entire practice. And it was something that I felt very deeply when I worked for him. I think most of all, he taught me that, you know, there's so many skills that you can— that can make you an exceptional lawyer, but to be a really good lawyer and to be a happy lawyer, you have to be a good person.

90And by that I mean, You know, don't cut corners. Don't lie to others. Don't lie to yourself. Always be truthful with the court. Your reputation is everything. Never mislead anyone. Understand that you have a function beyond serving your clients. You have a function to preserve the integrity of the administration of justice. Defend your clients with dignity. Always remind yourself of the values that brought you to this profession. Just having the privilege of working with him for so many years in that environment really helped kind of like screw my head on right when it came to criminal defense and always helped and helped me stay very closely wedded to the true purpose of why I'm doing this work and why I want to do this work and why I find joy and meaning in this work.

92No, no, no. Also, he didn't achieve me. Well, he did train you. He did, yes. I don't— oh, I don't know. I just— I don't think of him that way because I think Like, to me, it's like who he was as a person is what's more important. And he brought that energy, that integrity to everything. And so that everything was an achievement, even the piddliest, you know, guilty plea of a legal aid client versus, you know, a big precedent-setting case that he argued. Like, I think that to him, the integrity that he brought to each of those processes was what I took from my experience with him. So it wasn't necessarily a legal accomplishment because one thing that I've also learned in this profession is you lose a lot.

93You get a lot of— sometimes in criminal defense you actually represent a criminal and they will go to jail. So you have to be used to, you have to get used to that. And so it's the The process and the dignity and the integrity that you bring to that defense and the, the zealousness of your advocacy. That's what I, like, that's when I look at him, I, and I think about him and his legacy. That's what I think of, at least for me. I know he means a lot of things to a lot of people and he, he was a lawyer for 50 decades, 50 decades. I cannot possibly start to amass list of his best and most notable cases, but there are a multitude of them.

94But I don't know what he might say to that question, but I know that one of his proudest accomplishments was raising two beautiful children. Like, he loved his kids, and I found that to be very touching and beautiful and human. I, you know, had this impression that in order to be a successful lawyer, you kind of had to pretend that your family didn't exist or not show that softness, that, you know, not gleefully giggle about your family and the love that you have in your life. And I found that he took so much joy and pleasure in that, and that sort of gave me the license, the freedom to do that because it was— I had misunderstood that that was a weakness, but it was a strength that gave him meaning gave him passion, and I took that from him.

96So neither of my parents are lawyers. We immigrated to Canada when I was 10 years old. My, my mom is a teacher, extremely hardworking, ambitious, kind and generous and very motivated. And she very much saw her role as a teacher and then ultimately as a vice principal in a school as providing great meaning in her life. And that was very evident to me, not only throughout her career, but also at her retirement, the number of people who showed up to celebrate her and to talk about the important impact that she had in their lives. And I remember, you know, even growing up, we would, we weren't very well off, but my mom, you know, every Christmas would be gathering things for the students in her class who she knew their parents could not afford anything.

97So we would just, you know, try to put things together for them. She would bake for them. She would cook for them because sometimes she had students in her class who came to school hungry. And so just that nurturing sort of holistic sense that she brought to her work, I think, really resonated with me. And it meant that I, in choosing the path that I wanted to go down, it couldn't just be a job. I couldn't just be, you know, producing widgets. It had to be more integral to my personality, my character, and the meaning that I have in my life. And I would say that my mother did such an incredible job in modeling that with also being ever present for her children and working really, really hard and loving us unconditionally.

98So I think I had a great role model in that. And my father, when we came to Canada, was a foreign-trained medical doctor and it took him decades to— or not decades, sorry, years But I think maybe like over a decade. Yeah, about a decade to get relicensed as a medical professional in Canada and, and to start his own practice and become very successful as a doctor. And it took like watching him go through that and to persevere and to fail and get up again and requalify and in a whole new country. It was very inspirational. It meant that, you know, in the same way that you said that, ask and you shall receive.

99If you don't try, you will never get there, right? So you have to keep trying, and you are— there are times where you might fail, but just keep pushing. And I really learned that from my father.

101English, obviously. Slovak. What? Yeah, seriously? Yes, I'm half Slovak. My mom is— my mom is Slovak. Yeah, I was born in Bratislava.

103Who are your other Eastern European guests?

105speak Russian? Yeah,

107Oh yeah, yeah, yeah,

109my

111Oh, well, my mom—

113My mom is a Russian— Russian— before moving to Canada, my mom was a Russian professor, so she speaks Russian.

115She would love it.

117Slovak, and French.

119Oh, thank you. I really enjoyed reflecting on the questions that you asked. They're very thoughtful. And so thank you for that.