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Defence Lawyers in the Trenches Getting Coffee

I love Jerry Seinfeld´s show ´Comedians in Cars Getting Coffee´. Not only have I been a lifelong fan of stand-up comedy, but I think I have some insight into the concept behind the show – Jerry Seinfeld likes the interaction with his fellow comedians (and cars and coffee). Comedians tend to have a lot in common and get along and where they differ, it is interesting to sit down and talk about it. This is something I identify with and understand as a defence lawyer. I noticed how much I enjoyed the interaction with defence lawyers instantly when I became one and it is something that I have cherished ever since. It has been one of the delights of my life to just sit down with the interesting, smart and conscientious people of the defence bar and just learn from them. I thought with this #coronavirus lockdown, it was finally time to write down some of my favourite lessons I have learned over the years.

Jordana Goldlist

Before the release of R v. Anthony-Cook (the case that lays out a very stringent test and gives the option to the accused to strike his/her guilty plea before a judge can jump a joint submission on sentence worked out between the Crown and the defence), I was in court for an 18 year-old who was pleading guilty to a robbery. The accused had spent four months in pre-trial custody and I had worked out a plea agreement with the Crown for six months of custody (which is 4 months at 1.5 to 1 in pre-sentence custody) and a two year probation with the usual statutory terms and a non-contact clause with the victim. After my client had pled guilty and the Crown and defence had made submissions, the judge jumped the joint submission and imposed a TWO-YEAR probation with a curfew between the hours of 6:00 p.m. and 6:00 a.m. When I protested the 6:00 p.m. curfew and the length of the term, the judge indicated that the accused could always apply to vary the probation. I had an eerie feeling that this 18 year-old´s life was going to be forever marked by the ridiculous 6:00 p.m. curfew and his inevitable and repeated breaches of that order.

Fast forward a few years and I heard defence lawyer Jordana Goldlist state something bluntly that encapsulated that eerie feeling I had when I represented that 18 year-old and watched helplessly as the judge imposed a 6:00 p.m. curfew – the criminal justice system is designed to trap people in. We ought to really think about this and what it means in our present day, but also historically.

Things are improving with the release of R v. Antic and the presumption that bail will be on the least onerous terms, but how many lives were destroyed by pointless bail conditions like not to consume alcohol? Or not to contact someone like your husband or wife, even if they decidedly wanted contact? Or house arrest bails when house arrest was completely unnecessary (house arrest bails were practically the norm before Antic)? Or bails with the condition not to possess a cell phone when that condition was completely unnecessary? Or two-year probations for an 18 year-old with a 6:00 p.m. curfew? What if this is, or was, a feature of the criminal justice system and not a bug?

As Jordana points out, where would the judges, Crown Attorneys, defence lawyers, clerks, registrars, court reporters, probation officers, transcriptionists and court officers be without the accused? There is an undeniable incentive for them to create crime. There is also something deep within human psychology that causes us to take pleasure in other people´s misfortune. You are in court and see a rounder coming through who has been charged for the fifth time with breaching his 6:00 p.m. probation order and all of a sudden you feel better about yourself and your life. The Germans have a fabulous word for this phenomenon, Schadenfreude. There is also a saying attributed to Gore Vidal, David Merrick and others that taps into this psychological phenomenon that is in all of us as human beings (and that we ought to resist):

“It is not enough that I succeed. Others must fail.”

When Jordana came out and bluntly stated that the criminal justice system is designed to trap people in, I could finally explain to myself that eerie feeling I have often had (though must less so recently) that pointless court orders set up my clients to fail. And I have been thinking about it ever since. I am glad that Jordana had the courage to say it.

Annamaria Enenajor

About ten years ago, I got a phone call from someone trying to take his family on a trip to Washington D.C. by car. He was stopped at the border and told he could not enter the United States because of a conviction for simple possession of marijuana in 1992. You read that right. Like any right-thinking person, I was incensed. The conviction to start with was based on an act that was a stupid, pointless and mean thing to prosecute. I couldn’t believe it was reverberating twenty years later and ironically preventing a law-abiding man from taking his family to educate them and pay homage to the heroes of the United States like George Washington, Abraham Lincoln and Martin Luther King.

Before I met Annamaria, I was such a fan of hers for a lot of reasons, but especially because of her advocacy on behalf of Cannabis Amnesty. Every single conviction for simple possession of marijuana shuold be purged into the dustbin of history and evidence of it shredded. Annamaria in particular has taken the lead on this and I am grateful to her and others who are working on this very important initiative.

When I finally sat down with her for lunch recently, we talked for almost three hours. I learned a lot from our conversation, but there is one thing she said that I have been thinking bout ever since.

As we were talking, I launched into my familiar rant about how young law students have been dealt a bad hand by Baby Boomers. I could see that Annamaria did not agree with me as she looked at me with a disapproving look.

“What?” I said.

“Success does not happen overnight. Success takes discipline and resiliency and it could take ten or twenty years.” She responded, just as unflinchingly as you can imagine.

“For a lot of people graduating from law school today, they expect to become successful overnight and immediately post pictures of themselves on Instagram on lavish vacations or out for fancy dinners. That is not reality. Success takes sacrifice and time and you have to pay your dues. It can take years. My father had to recertify as a doctor in Canada and it took time and he never complained. We were all willing to sacrifice for a long-term goal and deal with setbacks and a lot of people in law school I speak to do not seem willing to do that.”

Forget the Baby Boomers for a moment, Annamaria’s definition of success is a much more traditional definition of it. Before the Baby Boomers, the Greatest Generation had a definition of success like hers. Success was much more of a long-term project. Nobody borrowed huge amounts of money from the bank to buy a house or car and flashed material wealth on social media then. People saved and sacrificed and were proud that they were able to use their savings to buy a home, or were proud they maintained their business, held a job or whatever long-term goal they had.

Even for someone who likes to rant like me, I had to reconsider after I heard what she had to say. She is right when she says success should be defined based on a long-term goal. Law is a marathon, not a sprint. There is nothing wrong with sacrificing and saving towards a long-term goal. In fact, for many years our society thrived and prospered from that view of success. Maybe we should start talking about that definition of success more often. I hope Annamaria will take the lead on that too.

John Struthers

Defence lawyers are constantly trying to point out logical flaws in people´s thinking. It is one of the important tasks in cross-examination. For example, I once had a police officer say someone wearing a black hoodie with the hood up was part of what formed his reasonable and probable grounds to arrest him because, in his experience, people who wear a black hoodie are trying to avoid being identified. But in my experience, people who wear a black hoodie with the hood up are cold. My point was, you cannot base your conclusions on your experience, it is a very logically flawed way of drawing conclusions.

I often say that I think the high point for our country, the good old days to use a colloquial phrase, were in the late 80s and early 90s. John follows me on social media, so he must know that this is my familiar refrain. I met with John recently who was ready to point out the logical flaw in my thinking.

“Everyone who talks about the good old days are not talking about how the good old days actually were, they are romanticizing youth.”

“What do you mean?” I asked.

“You were not an adult in the 90s, you have no idea what life was like. Of course you romanticize that time period, you were a kid and you enjoyed being a kid like anyone else.”

That was very true. I did enjoy being a kid. When I think about being a kid in the late 80s and early 90s, I think of playing Mike Tyson´s Punchout on Nintendo, playing street hockey with my neighbours, being taken care of by my parents and not having any responsibilities.

“The truth is, there were no good old days. It is a myth based on you thinking about your youth. And you cannot ignore that things are better now and there are more opportunities for people of colour than there ever were. That makes me happy. To me, these are the good old days.”

Then John continued his cross-examination of me.

“You are a pessimist.”

“Yes”, I acknowledged.

“I am an optimist. It is how we are wired.”

I couldn´t help but think that he is right about my impression of when things were best in our country. I was as illogical in my thinking as the police officer arresting my client because he was wearing a black hoodie with the hood up. I was a kid in the 90s, I cannot base when circumstances were best in our country based on my experience. John had me figured out, was prepared and got to the truth of the matter. It made me strangely proud of being a defence lawyer and appreciate the reason for cross-examination. It is truly the greatest tool for finding the truth that has ever been invented. I did not mind being cross-examined one bit and found it quite interesting to be on the other side of the table having my illogical thinking exposed. It is what I mean when I say that I always learn from my interactions with defence lawyers.

Sean Robichaud

I am a little biased when it comes to Sean because I have learned so much from him over the years. He excels as a lawyer, businessperson and podcaster, but he is to me first and foremost a dear friend.

Sean is on Twitter and Facebook, but what people who don´t know him don´t realize about him is that he would never be on social media if it weren´t for the fact that being a defence lawyer basically requires it. Sean likes to do activities like dirt biking, rock climbing and white-water rafting where you cannot even bring your phone with you and no one stops and takes pictures to post them. Sean would be much happier if he were not on social media.

Recently, we were talking about social media and legal awards and I launched into another rant about how criminal lawyers get shafted when it comes to legal awards. Criminal lawyers are the only lawyers who are routinely running and winning trials, but most of us labour in complete thankless solitude. Most of the general public does not hold us in high regard the way they once did in the era of Atticus Finch. Even most of our clients after they are acquitted disappear into the wilderness because they don´t want a reminder of the terrible experience they went through in going to trial. But Sean was not having my negativity and had a very good reason for not caring about awards:

“Awards to me are meaningless. Success to me is having a wife and children to share it with. I work hard and try my best to achieve things so I can share it with them and that is all I care about.”

In a world of social media attention-craving and like-counting, I needed to hear him say this and felt a sense of relief after he said it.

I have previously written about how the best thing that can happen to a legal entrepreneur is to get married to the right person if you are lucky enough to meet such a person. Sean was very lucky to meet his wife Shaun when they were very young and he is also right to not take it for granted. I knew exactly what he meant when he talked about how fulfilling it was for him to share success with his family. My wife has gone through every trial I have had for the last eleven years with me. Every time I hear the words “not guilty”, I immediately text her to tell her and it is one of my favourite things in the world because I know she genuinely cares about me and truly shares in my successes. Actually, she is a big part of them. Adi has helped me with every jury closing I have ever done. It is so important for me to go through my closing with her because I can very easily get lost in my own bullshit as a defence lawyer and I need her, someone who is not a criminal lawyer, to tell me when I am going too far down the defence-lawyer-rabbit-hole.

If you have someone who actually cares about your successes and shares in them, you should consider yourself very lucky. While social media likes and legal awards will leave you feeling empty, that will leave you feeling fulfilled. It was nice to be reminded of how lucky I am by someone who is a much better man than I am.

Todd White

This one is hard for me because Todd died recently and it came as a shock to me. Todd hired me to work for Greenspan Partners when I was just a bright-eyed kid with a dream of being a defence lawyer. I had articled at a Bay Street firm and getting a chance to work for a firm like Greenspan Partners felt like winning the lottery at the time and was the break I needed to start my career. I have previously written about how thin the line is between success and failure and how sometimes a lucky break can make all the difference. This was my lucky break. Todd and I just clicked in that job interview when I had exactly zero experience in criminal defence. There is never a day that goes by that I am not grateful to him for giving me a chance.

When I was at the firm, I used to do all the trials and prelims with Todd. I did my first murder case with him where the client had his charges withdrawn in the middle of the preliminary inquiry. My last case with him was an acquittal in a judge alone trial for a client charged with internet luring. 

Todd taught me a lot about cross-examination. Most importantly, he taught me that there are no short cuts. I am sure it was nice to have a junior like me to create a trial brief, summarize the disclosure and create neat cross-examination memos, but by the time we were at the trial or preliminary inquiry, it was obvious that he had read everything and done his own preparation. He looked exhausted. He often did not sleep before trials or preliminary inquiries as he would be so engrossed in his preparation.

I also learned that intense preparation is the lot of a defence lawyer. If you are a defence lawyer, I have some bad news for you: there is no point in your career where you will be wining and dining the clients while your junior does all the work, like a corporate lawyer might. If you are running a trial and doing it properly, you had better have read every word of disclosure and better be prepared for the cross-examination. There is no alternative. Todd taught me that.

I wish I had had the chance to tell him how much it meant to me that he took a chance on me and hired me and how grateful I am that I got to work with him. And that is the last lesson I learned from him. If you appreciate someone, tell them before it is too late.


This whole Covid-19 thing has me thinking about how much I enjoyed just the simple pleasure of going for coffee with my fellow defence lawyers. Like Seinfeld, I really enjoy the interaction and seeing how much we have in common. And where we differ, I like learning from you more than almost anything else. When this lockdown is all over, please call me, text me, DM me or stop me on the street and let´s go for coffee. I love hanging out with my fellow defence lawyers. You are my favourite people.


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