published 03/20/2026
It is with immense pride, and no small measure of bittersweet emotion, that we share that Jonathan M. Woolley, Partner at Thompson Dorfman Sweatman LLP, has been appointed a Judge of the Court of King’s Bench of Manitoba.
“Over the course of his career at the firm, Jon built something very special. He became one of the foremost construction law practitioners in this province, a lawyer whose name was synonymous with excellence, whose judgment was sought by clients in their most consequential matters, and whose skill commanded the respect of bench and bar alike,” said Keith LaBossiere, K.C., CEO and Managing Partner of TDS.
Extensive Legal Experience
Jonathan has a distinguished record in litigation and dispute resolution, representing clients in construction, infrastructure, and complex commercial matters before all levels of court, as well as in arbitration and mediation. He led TDS’s Litigation Practice Group with vision, integrity, and an unwavering commitment to the highest standards of advocacy.
“He gave generously of his time, his knowledge, and his counsel. He shaped the careers of lawyers at every level of this firm, and he did so with the quiet confidence of someone who understood that the measure of a great lawyer is found not only in the cases they win, but in the lawyers they help to build,” Keith LaBossiere added.
Education and Career at TDS
Jonathan earned his Bachelor of Arts (Hons.) from the University of Winnipeg, his LLB from the University of Manitoba, and a Master of Laws from Osgoode Hall. He was called to the Manitoba Bar in 2003, joined TDS, became a partner in 2011, and served on the Executive Committee, providing valued advice and counsel for many years.
A Commitment to the Law and the Community
This appointment reflects Jonathan’s professional excellence and dedication to the law, and underscores TDS’ leadership and longstanding presence in Manitoba’s legal community.
Celebrating Jonathan’s Legacy and Looking Ahead
While Jonathan’s appointment marks the conclusion of his distinguished career with TDS, we are excited for this next chapter in his professional journey. Keith LaBossiere reflects:
“His presence in the halls of this firm, his warmth, his wit and his integrity will leave a mark that no succession plan can fully account for. The bench gains an exceptional jurist. He brings to the role everything that made him exceptional as an advocate. The Court of King’s Bench is better for his appointment, and the parties who appear before him will be well-served.”
Our loss is profound, but Jonathan’s best work is still ahead and now in service of the public.
Please join us in congratulating Jonathan Woolley on this tremendous honour.
DISCLAIMER: This article is presented for informational purposes only. The content does not constitute legal advice or solicitation and does not create a solicitor client relationship. The views expressed are solely the authors’ and should not be attributed to any other party, including Thompson Dorfman Sweatman LLP (TDS), its affiliate companies or its clients. The authors make no guarantees regarding the accuracy or adequacy of the information contained herein or linked to via this article. The authors are not able to provide free legal advice. If you are seeking advice on specific matters, please contact Keith LaBossiere, CEO & Managing Partner at kdl@tdslaw.com, or 204.934.2587. Please be aware that any unsolicited information sent to the author(s) cannot be considered to be solicitor-client privileged.
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