Canada’s biggest festivals and sports events are increasingly sophisticated about risk – but the real pressure point is shifting to the country’s thousands of smaller community gatherings.
Michael McDermott (pictured), head of sports, entertainment and contingency at HDI Global Specialty SE Canada, said major organizers routinely spend tens of millions to stage events, which gives them the ability to bring in professional firms across the board.
“They can easily engage with professional firms, such as staging companies, security companies, bringing in third parties who will manage that exposure,” he told Insurance Business.
The picture changes sharply as budgets fall. McDermott said the real problems emerge with smaller organizers that either lack the budget to hire specialist providers or decide to handle everything themselves – and that’s where the risk really increases.
For insurers, the starting point remains traditional liability: what happens if a member of the public is injured at a game, festival, or concert. That includes not only crowd safety but also the equipment the organizer rents in – stages, bleachers, lighting, and temporary structures – and who is responsible if something fails.
McDermott noted that a significant part of the risk assessment comes down to scrutinizing the contracts between the organizer and third-party vendors – from who is actually responsible for security to who runs food, beverage, and concession operations, and whether those functions sit with the organizer or an external supplier.
He said contract wording can quietly transfer significant liability back onto the event owner, especially when multiple vendors are involved. Brokers who understand the space can often spot these issues before they become claims.
The same logic applies to the professionals behind the scenes. McDermott argued that event insurance should not be treated as a generalist line, either by brokers or by service providers.
“You don’t bring in a real estate lawyer to handle an employment issue, such as you don’t bring in a sound technician to do lighting, or to do crowd control,” he said. “You’re finding the right people and keeping people in their lane, knowing the lanes in which they trade in.”
He said the most effective brokers in the sector tend to be those who actively attend events, understand how they are run, and can talk to clients in practical terms about how staging, security, liquor, cannabis, food, and traffic management interlock.
He noted that event organizers should be working with brokers who have firsthand experience of these shows and festivals because those brokers understand how they operate on the ground and can speak to clients in practical terms they relate to.
Timing is another recurring weak point. McDermott said HDI regularly receives last-minute requests for general liability placements for events that are only days away. That limits what underwriters can do in terms of risk management support and structuring cover.
“A lot of the time that we get is a message that says that the event’s happening next week, and the organizers need a GL policy,” he said.
By contrast, when specialist brokers are involved from the outset, underwriting conversations can begin months before showtime. McDermott said these discussions typically start well ahead of time – anywhere from one to six months before show day, and in some cases as much as a year out, when planning is just beginning.
Early engagement also makes it easier to align insurance buying with budgeting. McDermott said HDI will provide indications at the planning stage so organizers can build risk transfer into their cost base rather than treating it as a discretionary add-on.
“We like to partner with our brokers and our clients,” he said. “So we can come up with a collective solution that meets the client’s needs, as well as providing adequate risk management practices and processes in place.”
