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All the while, Budman and Green remained visible promoters of the brand, pictured on the social circuit with celebrities and sports stars from Wayne Gretzky to Michael Jordan.

Roots’ backwards ‘Po’ Boy’ hat became the fashion sensation of the games and the momentum continued in 2002. But in 2005, Roots was outbid as the Olympic team outfitter by department store Hudson’s Bay Co., which has the contract until 2020.

Roots still has 115 Canadian stores, but scaled back its store count from a peak of 150 as the frenzy faded, and has reduced the size of some of its larger outlets over the years to put more resources into its online business. Budman later said the Olympics were terrific for sales, but took the company’s focus off of its heritage in leather goods, which are all designed and manufactured at its Toronto factory.

Uzumeri said Searchlight sees an opportunity to invest more in marketing the company, both in Canada and abroad.

“We think there is an opportunity to communicate the message more frequently and more actively,” he said. “(In Canada) I think there is a real opportunity for people who maybe shopped at Roots over the years and potentially haven’t been back in a store in a while.”

Sandy Silva, a fashion analyst at NPD Group Canada in Toronto, said while Budman and Green have done a “tremendous job” promoting the brand over the years, the retailer will do well with fresh owners who will be looking at the business through a more competitive lens. “The brand has been a bit quiet since those Olympic sponsorship days, and there is a middle ground in there to find between where they are right now and where they were during their Olympic heyday.”