After trading in his football gear for legal robes and choosing a career with the courts over one with the Canadian Football League (CFL), The Honourable Justice Lloyd Dean has not felt like he’s worked a day over the past 30 years. For 17.5 of those, he has sat as a judge in the Ontario Court of Justice, primarily in the criminal courts. In the 12 years prior, he spent six teaching full-time while working as a prosecutor part-time before transitioning to full-time. Justice Dean is also in his 13th year as a sessional instructor at the University of Windsor Faculty of Law. The journey to getting where he is now, happily retired but remaining as a part-time judge, has been nothing short of humbling.
Law was never a part of the original game plan.
Lloyd had never really planned on becoming a lawyer. While working towards his business degree, he spent two years playing baseball for a high-level travel team. After putting away the baseball bat, the football coach at the university, who was aware of Lloyd’s high school football days, approached Lloyd to ask if he would join the team. So, he did, and he played as a safety, a defensive back position, his last two years of undergrad. It was during his second year playing that some CFL scouts began talking to Lloyd. They had their eyes on him but thought he could use another year of experience before going pro.
With three years of sports eligibility left, Lloyd’s coach encouraged him to apply for law school because it too was three years. Lloyd also considered a year-long Bachelor of Education degree as he didn’t have high expectations for getting accepted into law school. After all, his focus to this point had been on becoming a professional football player and not on getting good grades. With his coach’s support, which included a few calls to some connections he had to the law school to get Lloyd’s application in front of the admissions committee, Lloyd became a law student, and the rest is history – sort of.
Why would you ever want to play professional football when you could be a lawyer?
Professional football was still the goal for Lloyd by the time 2L came around. However, things started to change when a CFL scout told him that teams would be weary of his commitment to playing once he had the option of joining the more stable profession of lawyering. Soon after, Lloyd injured his knee and his dreams of playing professionally were over.
Through a mutual love of football, Lloyd and the Associate Dean of Windsor Law developed a friendship that mostly revolved around Monday discussions about the weekend’s games. During a Monday chat, the Associate Dean, who was aware that Lloyd’s football career was over, asked him what he would do instead. Lloyd had no idea; he hadn’t applied for an articling position. Yet again, developing connections with people came through for him. The Associate Dean made a call and found Lloyd an articling position. Around the same time, Lloyd was asked to give a speech to the Law Society about his great-grandfather, who was one of the first black lawyers in Canada and the first Black in the entire British Commonwealth to receive the distinction of King’s Counsel. The presentation resulted in two more articling offers: one at a civil litigation firm, and the other in criminal law. However, Lloyd stuck with his original offer since it was a rotational program and he was still unsure if he wanted to even be a lawyer.
After articling, Lloyd ended up at the civil litigation firm that he had previously turned down. He was a 29-year-old former jock and power, money, and status were what appealed to him then. The firm gave him those things in exchange for six-day workweeks and the pressure to increase to seven. After 18 months of this lifestyle and a wife and young daughter at home, Lloyd decided that maybe this was not the profession for him.
“Most people think the grass is greener on this side and leave teaching to come to law.”
After deciding to go back to school to get his Bachelor of Education and before quitting his law job, Lloyd fortuitously, during an elevator ride, landed an interview that changed his life. On his way down from his sixth-floor office, he struck up a conversation with a friendly stranger whom he told of his plans to leave law for teaching. The gentleman asked him if he had ever considered being a prosecutor and Lloyd replied that it would likely be the only job that would get him to return to the profession. The gentleman put out his hand, introduced himself as Denis Harrison, Head Crown Attorney in Windsor, and informed Lloyd that their conversation had turned into a job interview.
Following a formal interview in May of 1993, Lloyd was offered a job. Before he could start, an Order in Council (OIC) had to be signed, as is the process before anyone can become a prosecutor. He was told that it would only take a few weeks. Though it would be tight financially, he felt comfortable enough with the prospect of living off his savings only for a short time, as he had quit his job and his wife, Helen, was on maternity leave. However, the months went by with no OIC in sight and he was forced to go on welfare (now known as Ontario Works).
October came around, no OIC had yet been signed, and the welfare representative told Lloyd that it was time to start applying for other jobs. He started supply teaching in Essex County before getting a full-time teaching position at a high school. Just a month later, Lloyd finally got some good news – the OIC was signed. Having just accepted the teaching position, Lloyd was in a difficult position. Instead of giving up either, he worked full-time as a teacher and part-time as a prosecutor.
In 1999, six years into this “best of both worlds” situation, a school board restructure left Lloyd with an ultimatum: continue teaching or become a full-time prosecutor. He took a leave from the school and accepted a six-month contract as a full-time prosecutor to test the waters. The change stuck and he was a full-time prosecutor by the beginning of 2000.
Lloyd loved that as a prosecutor, the outcomes that he worked towards could have positive domino effects for the victims, the accused, their families and the people around them, and in turn, the community as a whole. He missed teaching but knew that the door was not closed to it forever.
Who knows where your life is going to take you.
In February 2005, a position for a judge in the Windsor area opened. Despite his self-doubt telling him not to apply, Lloyd’s former professor and mentor, The Honourable Justice Saul Nosanchuk, and other judges wanted him on the bench because of his commitment to treating everyone he came across fairly, with respect and kindness. Months later, the Attorney General called to offer him the position – he was now The Honourable Justice Lloyd Dean.
As for teaching, once his children were grown up, Justice Dean accepted an offer to take over teaching a criminal law class. As a Windsor Law alumnus, Justice Dean has come full circle and has now been a sessional instructor at the school for 13 years.
“I am better than I deserve.”
From growing up as one of ten siblings living in a one-bedroom home, to being on welfare at 29, to becoming a judge at 41, Justice Dean’s experiences have humbled him. Everything he has been through has helped him empathize with others and become a judge who wants to help as opposed to punish people who have lost their way. The only difference between Justice Dean and many of the young offenders who appear before him in court are that they got caught.
Since October 1993, there has not been a day where Justice Dean has wished he didn’t have to go to work. That’s not to say that there are not days that are hard, but he credits his genuine enjoyment of his job to his passion for the work. You must be willing to make sacrifices but not at the expense of what’s most valuable to you. For Justice Dean, that’s his family. It is constant re-evaluation and communication, the willingness to learn from those conversations, and the need to improve and make those necessary changes that has allowed him to maintain a healthy relationship with his children and wife, whom he has been with for 43 years.
Nowadays, Justice Dean sits as a part-time judge and chooses to work only four or five days per month. Otherwise, he is happily retired. You can find him playing golf or pickleball with his wife, reading for pleasure while also keeping up with the law, and of course, following football.
“What you do for yourself dies with you when you leave this world, what you do for others lives on forever.” ― Ken Robinson
His wise mother used to ask for an opportunity to help at least one person every day, and Justice Dean has lived by that. If you do things for the benefit of others and not only yourself, you will be equally rewarded. Life is too short to follow a path set out for you by someone else. Follow your passion and as Justice Dean says, “Life is a journey, you don’t have to figure it out at 29, 30, 35. It’s only one time, so you better enjoy it”.