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It started with The Shot.

Kawhi Leonard’s buzzer-beater won the NBA Eastern Conference semi-final for the Toronto Raptors, and at a Toronto ad agency, it became clear that it was time to start printing some stickers.

Creative directors at Rethink, Mike Dubrick and Joel Holtby had pitched the idea for the Ka’Wine and Dine campaign earlier in the season. Two days after the shot moved Toronto one step closer to a championship, the agency had printed up roughly 400 stickers with the face of the most popular and least garrulous man in Toronto, offering free food as an incentive for Mr. Leonard to re-sign with the Raptors.

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Local businesses immediately jumped on the bandwagon, putting the stickers in their windows and, when the first 400 ran out, printing their own signs from the campaign website.

“It blew up overnight,” said Aaron Starkman, partner at Rethink.

But according to marketing experts, campaigns such as this that have cropped up during the long wait for news about Mr. Leonard’s future plans, may be playing in a grey area when it comes to the athlete’s control over his name and image.

“People are playing fast and loose,” said Brian Cooper, chairman of MKTG, a firm that negotiates sponsorship deals for brands. “ … You can’t use his name, or his number and jersey colour, or his image. … That’s appropriation of his intellectual property.”

Amid the excitement of the Raptors’ first NBA championship, marketers have been jumping into the conversation.

On Facebook, Kraft Heinz Canada offered the star player free macaroni and cheese for life, using the Ka’Wine and Dine logo. IKEA Canada took to Instagram to promote a $10 plant as “a housewarming gift for champions,” after a Toronto resident celebrating the win brought a plant into the streets that he said was a gift for Mr. Leonard. The furniture retailer tagged its post with “#Kawactus” and “#HeStay.” Toronto-based broker The Condo Store offered up a free penthouse.

But are brands that do not have sponsorship deals with either the National Basketball Association, the Toronto Raptors, or the athlete himself engaging in guerrilla marketing when they use his image − even if it’s just to build a bit of brand awareness on social media?

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In Canada, “personality” rights dictate that an athlete has to give permission for businesses to use any identifying features − including their name or likeness − in a commercial context.

“Looking to take advantage of a key event involving a player, a business may tread carefully and make only a skillful allusion to the player without mentioning that player or appropriating his or her personality,” said Eric Macramalla, an intellectual-property partner at Gowlings LLP in Toronto.

“Businesses, however, get into trouble when they use the personality of a player in a commercial context without that player’s consent. Players recognize there is tremendous opportunity to monetize their name and likeness. To that end, it is wise to take steps to ensure that any unauthorized use of their name or likeness is addressed.”

He declined to comment on any of the specific brands talking about Kawhi, but said that in order for something to count as misappropriation, the personality has to be clearly identifiable; used for a commercial purpose; and must suggest an endorsement by that person. “If you establish the first two elements, the third … will typically be established,” he said.

The question is whether it’s worth asking restaurants not to stick his face in their windows or even to hold larger corporations accountable for a one-off social-media post using his name.

“It’s a grey area,” Mr. Cooper said. “It’s not a sustainable program or an endorsement, but it is the halo of Kawhi and brand association.”

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On Wednesday, Boston Pizza International Inc. posted a GIF of Mr. Leonard on Twitter, with an offer to change the name of its Hawaiian pizza to the “Kawiian pizza” if Mr. Leonard stays in Toronto. (The restaurant chain would do this only for online ordering and will not be reprinting any menus.) It also offered free Hawaiian pizzas for life to the star − which is either a mouthwatering or horrifying prospect, depending on your point of view of that contentious topping pineapple.

“I’ll stop short of calling it ambush on social media, but social media does become an outlet where you can join a part of the cultural conversation without paying for six-figure or seven-figure sponsorships,” said James Kawalecki, Boston Pizza’s senior director of sports and sponsorships. “The thing you always try to do is make sure you’re not trying to falsely create a connection to a property that you don’t have rights to.”

The company is a sponsor of the Toronto Blue Jays, four National Hockey League teams, and Ultimate Fighting Championship Canada. The brand has seen the issue from a sponsor’s perspective when the conversation takes off: The Blue Jays playoff run in 2015 is one example. Sponsors have to work hard to stand out when others are trying to be part of a cultural phenomenon, Mr. Kawalecki said, but ultimately the excitement services to increase the value of association with a winning team or player.

In the case of Ka’Wine and Dine, Rethink’s client − a fansite called Raptors Republic − got a lot of press, Mr. Starkman said.

“He doesn’t need a free meal. He doesn’t. We know that Kawhi is not going to choose to stay based on getting free dinners,” Mr. Starkman said. “But the whole point was essentially to give a giant love letter to Kawhi, that the fans, local businesses and the city as a whole have his back, support him and want to really treat him like a hero.”

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