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Gary and Penny Gilmour
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Since 1976, Gary Gilmour has been a fixture in Winkler through his law practice. After an impressive career that spans almost five decades — with a collection of accolades and achievements along the way — Gilmour is retiring.  

“At the time I got here, I was the only lawyer living in Winkler,” he says. “There were two other offices that came in on a part-time basis where the lawyers then returned to their main offices, but I was the only lawyer living here.” 

These days, more law offices have been opened in town, but Gilmour will always hold the legacy of having been here since the beginning. He has provided an essential service to generations of Winklerites.  

“Through the years I've had a number of different partnerships, sometimes working as a sole practitioner as well,” he says. “Over that time, we've provided general legal services to people in Winkler, so that's largely things like real estate services, small business services, wills and estates, [and] a lot of family law.”  

Gilmour says that when he first arrived in Winkler, he already had experience as a lawyer from his articling days in Winnipeg. The training translated to this community well. It was relatively easy to adjust to working in the Pembina Valley. 

“As to where I thought the firm would go in those days, I thought I would probably be here 5 to 10 years and then move on to something else, but professional relationships developed with clients, and those weren't necessarily movable to another firm, so I stayed on,” he says. “At the same time, Penny [my wife] and I had [other] relationships in town with things like the Lions Club and the Chamber of Commerce and the Community Foundation. All those connections kept us here.”  

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Partner Loren Braul with Gary Gilmour at retirement party.

Through the decades, Gilmour has witnessed the changes that the legal industry has undergone.  

"Really everything has changed,” he says. “Back in the 1980s, there were no computers. All court appearances were in person. Now a lot of court work is done online so that the lawyers don't have to travel as much, which makes a big difference when you're in a rural area.” 

Gilmour says that the changes have transformed how one practices law. Even so, the journey has been worthwhile for him. Gilmour says that when he thinks back to the highlights of his career, they are mixed with successes that happened away from the law office. 

“One thing we managed to do, and this was not as a lawyer, although I did the legal part of it, but more as a Lions Club, was setup of the Amy Janzen Fund, which is still functioning and with which actually I'm still involved,” he says. “[It’s] a fund that assists people with medical costs that aren't covered by Manitoba medical [coverage]. That was quite an accomplishment.” 

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Gilmour has also enriched the community by teaching legal courses at Red River College, organizing blood donor clinics in Winkler and Altona, and sitting on the boards of the Winkler Community Foundation and the Lutheran Church of Canada. In 2013, Gilmour was named the Citizen of the Year for his efforts in Winkler, and in 2021, he was one of 150 citizens recognized across the province for making Manitoba a wonderful place to be.

There are of course also some legal cases that stand out to Gilmour as high points in his career.  

“I have certainly had some legal successes over the years that I was really pleased with,” he says. “What stands out, I think, is that we were able to establish an office that has operated all these years and provided the services it's provided . . . . It means a lot when local residents can obtain legal work without having to drive the 75 miles into Winnipeg.” 

As for what’s on the horizon, Gilmour has no firm plans, but there are some big changes in the works, including moving to Winnipeg with Penny. 

“What I've observed with retiring people in Winkler is that those who retire in reasonably good health normally end up getting snapped up by nonprofit and charitable organizations,” he says. “I'm open to that. I'm looking around [for] what I can get involved with in Winnipeg. At the same time, we're establishing or reestablishing contacts for things like exercise . . . and stuff like that.”  

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Gary Gilmour with FCPA, FCGA Dale Gislason partner of Gislason Targownik Peters 

Gilmour says that he also looks forward to spending more time with his granddaughter who lives in Winnipeg, and there may also be some travel for the Gilmours in the future.  

A celebration was held to commemorate the close of a significant chapter in both Gilmour’s career and Winkler’s history. Gilmour had straightforward expectations for the event with his colleagues.  

“I'm hoping . . . we can discuss old times and try to avoid getting into serious discussion as to legal matters they might need in the future,” he says. “We'll see where it goes.” 

~With files from Robyn Wiebe~ 

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