From the streets to the courtroom

Law school grad fulfils lifelong dream at 49, after being homeless and battling addiction


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“It’s never too late!” Sean Gallop wrote above his graduation photo in a social-media post that would go viral.

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Hey there, time traveller!
This article was published 03/08/2021 (420 days ago), so information in it may no longer be current.

“It’s never too late!” Sean Gallop wrote above his graduation photo in a social-media post that would go viral.

He’d just finished law school at the age of 49, decades after he dropped out of high school to work at Pizza Hut. One of the guys he worked with back then was among more than a million people who viewed Gallop’s LinkedIn post. He got a congratulatory message from him — one of thousands from all over the world. Many wanted to know: how did he do it?

“I said, well, just make a plan,” Gallop says in an interview. “If you want to do something, make a plan, start researching and then follow through on your plan.”

JOHN WOODS / WINNIPEG FREE PRESSSean Gallop, who battled addiction and homelessness in the past, is photographed in a park he would frequent before his law career Wednesday, July 28, 2021. Gallop Started law school in his mid-forties and graduated this year at 49. He is currently articling at Legal Aid and plans to continue doing legal aid work and “give back hope”. Reporter: May

It sounds straightforward, but it wasn’t easy. By the time Gallop decided to study law, he’d battled drug addiction, been homeless on the streets of Winnipeg, attempted suicide, and, yes, needed a lawyer. But when he graduated this spring as the oldest student at University of Manitoba’s Robson Hall and began articling at Legal Aid Manitoba, Gallop was fulfilling a teenage dream. He’d wanted to be a lawyer since he was in high school, before he became homeless for the first time as a teen.

“I’d like people to think to themselves that if they had a vision or a dream or an idea or something that they wanted to do, it was given to them for a reason, and it is possible and they can achieve it,” he says. In other words: don’t give up.

“Because, quite frankly, I gave up a long time ago on this, and then it came back around again, and here I am.”

Gallop grew up in Ontario and arrived in Manitoba in 2000 as a member of the Canadian Armed Forces stationed in Winnipeg at the former Kapyong Barracks. He was a private working as a cook.

“I was a big drinker when I went into the army, but I had never touched hard drugs,” he says. His drinking escalated after the death of his brother, and he started using crack cocaine. Eventually, he was discharged from the military on a medical release. He wound up on the streets of Winnipeg using fentanyl and methamphetamine. By the time he went to a detox program six months later, he was injecting drugs — a fact he doesn’t want to shy away from, in case being explicit about it helps someone else in their recovery.

He was charged with assault while on the street. A legal aid lawyer defended him, and Gallop got a conditional discharge, sparing him from a conviction. It would be years later, after working within the justice system, that Gallop would start to envision his own legal-aid career path as a way for him to help other people in the same position.

He got into a residential treatment program at the Behavioural Health Foundation, but completing it didn’t change the fact he didn’t really know anyone in the city. He didn’t do well on his own, and he didn’t kick the addictions on his first try.

“My success has a lot to do with the social programs I was able to access,” Gallop says.

He had to learn how to ask for help.

“The thing is not just asking for help, but once you ask for help, take the help that’s been given to you,” he says, now nearly 12 years sober. “Don’t say, aw, I’m going to wait for better help. Ask for guidance and then take the guidance that’s given to you as opposed to waiting for something else.”

He applied the same logic to getting through law school.

“That’s when things really changed for me, not just law-school-wise, but my personal life, being able to overcome addictions and that kind of stuff, it was asking for help and then taking the help.”

Before he could get to law school, though, Gallop went back to the foundation, years after undergoing his own treatment, and asked for a job. He became an addictions worker, and then a court worker tasked with doing risk assessments on people who had been charged with crimes and whose bail plans were to go to the foundation for treatment. It was his job to decide who would be accepted into the program. They’d then go before a judge, with an approval from the foundation boosting their chances of getting bail.

“I wasn’t always right, because there was people that I did deny who later reapplied and got in and they did exceptionally well,” he acknowledges.

Through years of listening to the men’s stories — trying not to get jaded if he heard the same tale repeatedly — Gallop realized just how common it was to struggle with addiction and intergenerational trauma.

“A substance abuse issue is usually a symptom of the problem and underneath it, all of them had some sort of complex trauma,” he says.

He sat in court and saw lawyers in action during bail hearings, such as the ones he runs now. Many of those lawyers, as well as correctional officers and other justice officials, became his cheerleaders as he went back to school. It was a local lawyer, he says, who first encouraged him, saying, “You know, you could do this. You could practise law.”

Gallop remembers thinking about it on his drive back to the foundation, pulling into a parking lot and phoning the University of Manitoba admissions office the same day.

JOHN WOODS / WINNIPEG FREE PRESS Sean Gallop says achieving your dreams all starts with a plan. The 49-year-old, who battled addiction and homelessness in the past, is now a law school graduate. Gallop says his past isn’t something to put behind him, it’s something he want to use to help others.

“I do that in my life now, I try to encourage people. Even in small ways, because I’ve experienced it. A small amount of encouragement can change people so easily that you’re not even aware of it, I think, because that’s what happened to me.”

He got his GED at 42, enrolled in online and night school university courses, excelled in them, and wrote the LSAT at 46. A program for mature university students allowed him to apply to law school after completing one year of university courses.

“I felt like I had to do it; I had to go for it,” Gallop says.

“One of the things I thought about the whole time was time’s going to pass either way.”

Looking back, Gallop says law school was a much more supportive environment than basic training. There was a certain freedom to being older; he wasn’t bound by cliques. He made it his mission to talk to everyone in his year, and became popular among his much younger peers, most of whom heard only little bits of his story leading up to graduation.

He landed in Stacey Soldier’s Indigenous law class. As someone who worked her way through law school as a single mother in her 30s, Soldier recognized the value of Gallop’s life experience. She’d seen him work with foundation clients, and knew him to be personable and effective.

“I remember thinking about it, thinking even if I didn’t know him, this guy is going to be a superstar. The clients are really going to like him,” she said.

His compassion and real-world understanding sets him apart, Soldier said, and his first-hand experience could go a long way in criminal law.

“For a long time, I was the only First Nations female lawyer practising criminal law in Winnipeg,” she says. “That does make a difference in terms of clients who can see someone that looks like them in the courtroom, speaking to the matters in a suit, being on their side.”

“Bringing a different voice and a different viewpoint to the legal community at large, I think, is quite important.”

His past isn’t something to put behind him, Gallop says. He wants to use it to help others.

“If anything, I’m living the dream of the hope that I had. When I was living on the streets, I had nothing and I thought it was the end of the world,” he says, reflecting on how much his life has changed. He hopes to work for Legal Aid after he’s called to the bar and officially becomes a lawyer, and he still volunteers at the foundation.

“I want to give back hope.”

Twitter: @thatkatiemay

Katie May

Katie May

Katie May is a general-assignment reporter for the Free Press.

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