Jack Keokanock started his construction career in the field before moving into project planning, contract management and commercial leadership. As contracts became an increasingly important part of his work, he wanted to better understand the legal framework behind the prime contracts, subcontracts and other commercial agreements he had been working with for roughly a decade.
When Osgoode launched its Professional LLM in Construction Law, Jack recognized much of his own work in the curriculum. “It really was going over the things that I was doing day to day,” he says.
The program has changed the lens through which Jack approaches those agreements. He describes contracts as “risk allocation tools,” considering issues such as human resources, delays, conflicts and payment terms alongside project execution.
“I find myself looking up case law a lot more,” he says, drawing on frameworks from the program to break down problems and identify relevant rules.
The evolving litigation in Walsh Construction v. Toronto Transit Commission et al provided a timely example of how case law could inform Jack’s approach to contract drafting. With rulings in the case continuing to generate discussion while he was completing the LLM, Jack followed its implications for subcontractor flow-through claims and how subcontract language, releases and risk allocation can affect a general contractor’s ability to pursue recovery from an owner.
“That’s one case I would say is particularly significant to construction law right now.”
Jack sees delay and change management becoming particularly relevant as construction projects grow larger and more complex. New legislation and court decisions can affect how contractual issues are handled, while projects still rely heavily on human judgment. Differences in experience, working styles and company perspectives can influence how the same contract or project issue is interpreted.
Studying alongside professionals from across the construction industry gave Jack access to many of those perspectives. His cohort included people with backgrounds in law, design, general contracting and claims consulting.
“I can’t overstate how important that was,” he says. “The mix of different backgrounds really helped the learning experience.”
Classroom discussions often drew on challenges students had encountered in their own work, while a cohort WhatsApp group has allowed the exchange to continue beyond the program. Jack has also maintained professional relationships with classmates he can reach out to when relevant questions or opportunities arise.
“What it really reinforced for me is the importance of resolving issues early on.”
Jack brings more of a cost-benefit analysis to negotiations with clients, subcontractors and others, considering what a dispute is worth pursuing and what the parties are likely to gain from escalation. In some cases, he says, mediation or arbitration can ultimately produce a resolution the parties might have reached themselves months earlier.
Earlier in his career, Jack was more inclined to escalate an issue and leave the legal process to unfold. Understanding where that path can lead has made early resolution a greater part of his approach, alongside identifying contractual risks before they develop into larger project disputes.
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Jack Keokanock – Executive Vice President, Yellowridge Construction Ltd.
Graduate of the LLM in Construction Law (2026)