James McGregor spent more than a decade scouting top talent for the NHL and Ontario Hockey League.

Seeking a change of pace from a hectic schedule on the road with Oilers Entertainment Group, the husband and father of two started a new journey in real estate in 2017, finding ways to apply his background in professional hockey to selling multi-million-dollar homes in Southwestern Ontario.

McGregor, a founding partner of McGregor Hahne Group, has found an edge in dealing with a high-end homes, and even high-profile clientele, as member of Engel and Völkers’ Professional Athlete Advisory.

From arenas to open houses

McGregor, who lives in his hometown of Owen Sound, studied sports management at Brock University, and after finishing school headed west to Edmonton where his first job was selling Oilers tickets to non-profit groups. 

He steadily moved up in the organization as a scout, and in 2012 moved back home to Ontario to help run the Erie Otters OHL team. 

When he transitioned into real estate, initially with Homelife Bayside Realty Ltd., he brought years of experience negotiating player contracts into the role, and skills that translated naturally into real estate. 

“The experience you gain in the uncertainty of sports helps you navigate through the ups and downs of the real estate world,” he said.

In his early years in the Oilers organization, McGregor was mentored by then-general manager and Oilers veteran Kevin Lowe, and then-assistant GM Scott Howson, who is now CEO of the American Hockey League. 

McGregor still uses strategies in real estate deals today that he learned for negotiating player contracts back then.

“The key to negotiation is being thoroughly prepared. Know your best alternative to a negotiated agreement, and stick within that, working toward the goal of what your people want to get out of it,” he said.

No sticker shock

Years of negotiating multi-million-dollar contracts made the financial side of real estate feel familiar to McGregor. 

Some newer agents can be intimidated by deals in the millions, McGregor said, but he was used to seeing contracts worth seven figures (or more).

While with the Oilers, he handled contracts ranging from hundreds of thousands to tens of millions, he said.

 “In professional sports, you’re dealing with large sums of money all the time,” he said. “So I wasn’t intimidated by what a house would sell for, or seeing those big numbers.”

A ‘hotbed’ in Muskoka

According to McGregor, serving professional athletes in Muskoka is less about the athlete and more about their inner circle. 

“Really, at the bare root of it, you are dealing with their team and their family more than the actual athlete.”

He said Muskoka and the Georgian Bay area have become hotspots for secondary homes, especially among hockey players. 

These aren’t flashy real estate deals—they’re deeply personal. Athletes are buying summer homes as a retreat for their families, he said.

Skip the selfie

Discretion is paramount when working with professional athletes, said McGregor. 

“They are in the media, they’re a part of it, and the last thing they want is exposure in another way, which is in their private lives.” 

As tempting as it may be to take a selfie or share who you’ve just worked with, that instinct must be resisted, he said. 

Glamour and glitz may define the surface of professional sports, but there’s a deeply personal layer beneath it, especially when athletes and their families are relocating. Respecting their privacy isn’t just polite, it’s essential to doing business in that world, he said.

Offer a complete package for life after the transaction

Building trust with professional athletes goes far beyond the transaction. 

“They wanna see competence, they wanna see that you’re professional, that you’re serious, reliable, and that you’re networked within the area that…they’re looking to move.” 

It’s about showing you can deliver, not only in the deal itself, but in everything that surrounds it, he said.

Athletes and their families often relocate to unfamiliar cities, so offering support that helps them settle in can add immense value, from recommending discreet service providers to helping locate daycare or a trusted doctor, said McGregor.

Network, network, network

Establishing yourself in the professional athlete market is entirely about networking, said McGregor.

 “It would all be networking. I don’t know that there would be a way to do it without,” he said.

Breaking into this world requires meaningful connections with players, agents, team owners, and staff, and relationships that open doors and build credibility, he said.

Courtney Zwicker

Courtney Zwicker is a digital reporter and associate editor for REM. Based in Atlantic Canada, she has over a decade of experience covering daily business news.