Dispute resolution
Fillmore Riley

Founded in Manitoba more than a century ago, Fillmore Riley today stands as one of Winnipeg’s most often-mentioned legal shops. Although a full-service firm, peers are quick to identify key litigators there as being some of the best in the province. “They have the largest insurance department between Ontario and Calgary,” observes a peer. “If there is any insurance filing that comes through Manitoba, Fillmore Riley is going to have a piece of it.” One devoted client weighs in, “Fillmore Riley have an excellent insurance litigation department with all levels of experience. They are considered by the insurance industry as the top firm for this type of litigation matter.” Peers make sure to note, however, that “they are not just known for insurance. They have a broader repertoire.” In particular, one peer observes, “They have quite a few people doing trust and estates work, and they have really raised their game in the tax area, too.” In the latter two practices, Cy Fien is a noted standout. A peer insists, “We need to talk more about Cy! He’s an absolute star in terms of tax! Not just in this province, either – He’s known all throughout Western Canada.” Bernice Bowley, typically touted for her prominence in the firm’s celebrated insurance practice, has also raised her profile in other areas, namely the tax and municipal law areas. Acting for the defendant, Bowley brought a successful summary judgment motion dismissing the plaintiffs’ claim for damages arising out of tax sales of certain properties. The client’s motion for summary judgment was granted, with a consolidated action being dismissed. The plaintiffs appealed to the Court of Appeal, although past the deadline, and had to bring a motion seeking leave to appeal. That motion was dismissed with costs. Bowley also, along with Brandon Barnes Trickett, acts for a leading hydroelectric engineering firm headquartered in Québec, the defendant in a contract and tort claim related to Manitoba Hydro’s high-value infrastructure redevelopment and upgrade. “Bernice is our counsel of choice,” confirms a client. “She has a wide range of experience and has the ability to adapt to the many different situations in which we become involved.” In the firm’s insurance capacity, Stuart Blake continues to draw acclaim, boasting a “who’s who” list of clients in both the local and international insurance realms. Blake’s practice also comprises a fair bit of aviation work. “Stuart does most of the aviation work in the province,” confirms a peer. Blake acted for the insurer of the defendants, a group of farmers who allegedly caused flooding that adversely affected the plaintiff, also a farmer. Blake successfully struck the claim prior to trial on the basis that the plaintiff violated earlier orders of the Court. Andrew Loewen is also said to be keeping very busy with practice that balances insurance and insolvency work.

Hill Sokalski Walsh

Founded in 1988, the boutique firm Hill Sokalski Walsh is noted for cultivating “a healthy mix of litigation files,” according to peers. “They keep it interesting! They take on any files they want and work them with equal vigor. It could be a ‘bet-the farm’ case or it could be an employment case – either way they’ll take it on and deliver the goods.” Firm founder Dave Hill is uniformly praised by peers. “Dave is certainly one of the most active litigators in Manitoba, hands-down.” Another peer elaborates, “I’ve had two cases in which I acted against Dave Hill. They were two pieces of commercial litigation, two credit unions, dealing with creditor’s rights, and Dave was a spirited fighter, as always.” Another elaborates, “Dave, and his firm, have noticeably been attending to a lot more plaintiff work as of late. He doesn’t always win the case[s], but he sure has the backbone to keep bringing them.” Hill lays claim to a precedent-setting win for his client in a case against the City of Winnipeg. After obtaining a rare mandamus against the City in 2018 on behalf of a developer client, in 2019, after the City did not follow this order, Hill was successful in having the City found in contempt. The ruling was issued in August 2019. As a follow-on, Hill led his client through three more contempt hearings, after which the City counselors changed their minds and granted the client the zoning permits that were originally denied. Now that this has been approved, Hill has filed a $30 million suit against four individuals who allegedly obstructed the case along the way. This case is scheduled for an eight-week trial in October 2021. Hill’s triumph in this matter has driven an increased level of other municipal work to the firm. Sherri Walsh has recently been appointed the first Appeals Commissioner outside the City of Winnipeg, a provincial appointment. Bob Sokalski is still noted for a lot of work in the sports and defamation areas. “He does mostly administrative law stuff,” declares a peer. “He acts for a lot of people who have been disciplined by certain associations. He wouldn’t be involved in trial work at all but he’s known as ‘The Motion Man.’” The firm has also kept its eye on building out at the younger level, welcoming Kevin Toyne to the partnership. Toyne, originally from Toronto where he worked in that city’s office of Davies Ward Phillips & Vineberg, makes his debut appearance in this edition of Benchmark Canada.

MLT Aikins

Prairie powerhouse firm MLT Aikins is the product of a merger between two firms, Saskatoon’s McPherson Leslie & Tyerman and Winnipeg’s Aikins, both of whom individually held historic prestige in their respective jurisdictions before combining in 2015. The Winnipeg office received a youthful boost last year when it hired Christian Monnin, formerly the managing partner of Hill Sokalski Walsh and someone considered by peers to be “of judicial royalty.” More recently the firm’s Winnipeg received another boost of horsepower when Michael Weinstein, a partner known for a locally robust construction practice, was another former Hill Sokalski partner to join the firm within the past year. Monnin was part of a legal team representing the Assembly of Manitoba Chiefs, who were granted intervener status in a case about language education rights for French speakers in British Columbia. The Supreme Court has to decide what school services BC must have for its French-speaking community. While at his former firm, Monnin finished a two-week trial in November 2018 on a matter that dealt with the issue of law of chance/loss of opportunity as it relates to a failed real estate transaction. Monnin was part of a team acting for the plaintiff, a real estate and hotel developer who was relying on the assistance of a commercial real estate agent. The commercial real estate agent ultimately acted for another real estate developer who was successful in the purchase. The client pursued the real estate agent for several millions of dollars. In addition to his civil litigation practice, Monnin also has a labor (management side) practice. In this regard, he just finished a lengthy collective bargaining with a public institution while dealing with the Public Services Sustainability Act, which was introduced by the Provincial government in the Spring of 2017 and sought to freeze the wages of 120,000 public-sector workers for two years and cap their pay for another two years.


A Winnipeg full-service firm, Pitblado houses a diverse array of practitioners handling cases related to commercial litigation, labor and employment, construction and financial services. Tracey Epp deals primarily in labor and employment, along with judicial reviews, while Jeff Baigrie’s practice encompasses a mix of all of the aforementioned practices. Steve Vincent, primarily a commercial litigator, had a trial win in December 2019 concerning two parcels of land in dispute between two parties, which was eventually fenced off by Vincent’s client, leading to claims filed by the plaintiff, which were dismissed. More recently, Vincent has scored on behalf of his client when a trial decision was rendered arising from a five-week trial from more than two years ago. Vincent acted for a lawyer who was alleged to have acted for an elderly farmer who lacked capacity to sell his farmland in retirement, which was sold for millions below fair market value. All allegations were dismissed; the farmer was found to have capacity, the lawyer was found to not have been negligent, to not have caused any loss to his estate and there were no compensatory damages. Vincent is also engaged in commercial litigation between entities in the security alarm business.

Thompson Dorfman Sweatman

One of Winnipeg’s largest independent firms, Thompson Dorfman & Sweatman’s reputation is held aloft by some vibrant peer review. “TDS is doing a good job at diversifying,” declares one contemporary. “They’ve got some great talent over there like Lynda Troup, who has a broad commercial practice, and Jonathan Woolley, who’s got a pretty healthy construction practice on the go.”

Managing partner Keith LaBossiere balances a labor and employment litigation practice with his management duties. He is lead counsel for MGEU Paramedics of Winnipeg in a high-profile case resulting in a significant $100,000 damage award against the City of Winnipeg in a labor arbitration. LaBossiere is also lead counsel on behalf of the WPA, representing the front line police officers employed by the Winnipeg Police Service in another high-profile case resulting in a finding in favor of his client and resulting in a finding that the employer was placing members in an unreasonable safety risk in dealing with the opioid crisis. The case resulted in much-needed safety equipment being provided to police officers in Winnipeg. It is also noted that “Ross McFadyen has really come to the fore in taking on their major litigation matters,” according to one prominent peer. “In the general commercial litigation community, he’s the one I see the most.”