Portland Winterhawks: Introducing Greg Sampson

As the 2022-2023 WHL regular season concludes and the attention shifts toward the playoffs and, eventually, the CHL Memorial Cup, life in hockey operations continues to run at a million miles a minute. 

For Greg Sampson, the Director of Hockey Operations for the Portland Winterhawks, the fast-paced environment is part of the appeal and excitement of working behind the scenes for one of the premier organizations in the WHL. 

“That is what I love about this job,” he said about not having the same routine day-to-day. 

Sampson is in his second full season with Portland after making the 2,865-mile (4,610-kilometer) journey from his hometown of Middleton, Nova Scotia to the Rose City. 

How does someone from about as far east in North America end up working in Portland? 

“It was a roundabout way to get into the role I’m in currently. I was working as a lawyer in Nova Scotia. It was fellow Nova Scotian Mike Johnston (Winterhawks Senior Vice President, General Manager, and Head Coach) in the summer of 2021. He offered me a role here with the Winterhawks. We stayed in touch over the years through hockey, and he kept tabs on my academic and professional background. It made sense at the time, and I took the leap of faith to move out here to Oregon,” Sampson said. 

Johnston was excited to get someone with Sampson’s background into the organization. 

“After the COVID season, we were searching for some more people to work in the office who had different skill sets. A friend of mine in Nova Scotia who I grew up with; I knew his son Greg Sampson. I knew he was a lawyer and was maybe looking at getting back into hockey. I just threw it out there that if Greg wanted to get back into hockey, here was an opportunity for him. You can come into an organization like ours where you can do some scouting, some hockey operations, and help out in other areas as well. He has his master’s degree in (Sports Management); what an overall great skill set. We talked to him about the big move and the change of jobs from his lawyer position. He was interested in it and has done outstanding work,” Johnston said. 

Sampson played hockey at the AAA level but turned down a Junior A opportunity to begin his academic work. However, everything he did had the focus on getting back into hockey. 

Sampson helped organize a charity hockey game while completing his undergrad degree and read anything he could to stay current with the business side of hockey and the NHL. He completed his master’s at Columbia and spent nearly six years in the legal profession. 

“My hope was to apply my legal education within sports someday, not necessarily to be a lawyer, although I’m glad I do have that experience, and I’m glad I could bring that back into hockey,” Sampson said.

Hockey Operations 

Upon completion of his master’s degree, Sampson contacted Cam Russell, the general manager of his hometown Halifax Mooseheads, to see if they had any opportunities. 

“I asked him about possibilities and if they would be willing to take me on board. Sure enough, they did have a need, and there was sort of a mutual fit there. I did that for one season with Halifax to get some experience and then parlayed that back into Hockey Nova Scotia working as a camp coach for their High Performance program as an evaluator to help select the teams,” Sampson said. 

Portland soon had an opening within its Hockey Operations department, and Johnston needed to fill the void. 

“Lisa’s (Hollenbeck) role has continued to evolve over the years to the point where she is now a vice president (Vice President of Operations) in our organization. When she moved up to that level, it created a vacancy. We needed someone to pick up the full-time work and someone who could be in the office. Mike Coflin (Assistant to the General Manager and Director of Scouting) is out scouting and is working with our regional scouts. We needed somebody here in Portland. We were looking for somebody with a certain skill set who knew hockey. We didn’t think we would find someone with a legal background, but it helps us a lot. Greg was the right choice for the job,” Johnston said. 

Mike Johnston (Photo: winterhawks.com)

What exactly is Hockey Operations, though? Every organization throws out that term, but what exactly does someone do who works in that department? 

“It is different for a lot of teams, and that title means different things to different organizations,” Sampson said. “For us here, we are pretty lucky as we have a really expansive staff, an experienced staff. I try to basically slot in and add value where I can.” 

Some of those roles include helping Johnston with day-to-day tasks, organizing players’ travel to and from Portland (especially prospects or at training camp), working with game-day officials, conduit between agents and scouts who come to games, and more. 

In addition, Sampson also oversees the Winterhawks U.S. scouting and recruitment, which keeps him even busier than he already is. 

Need more work on your plate? 

“I’m also in with the coaching staff between periods and after the games adding any feedback that I see which might be unique from what they’ve observed during the game from the bench. Essentially, I’m being an extra set of eyes. We always like to say around here, ‘We all have other duties as assigned,’ and we wear different hats. Whether that is pitching in with our marketing team, sponsorships, or somewhere else, I try to just add value where I can,” Sampson said. 

No day is the same when you work in Hockey Operations. 

“I think the variety is part of the beauty of my job,” he said. “A day or a weekend scouting is certainly different from the day-to-day here in Portland while the team is here. When the team is here, I will try to watch practice so I can stay on top of how things are progressing there. I will observe the process in practice and also gauge where guys are at in their careers and the season. I will watch our road games, obviously, but that is also when my own travel schedule can conflict. I will try to get out of town to scout while the team is on the road. If I’m not, and I’m in Portland, I’m sort of the ‘boots on the ground’ guy here while the team is away. I’m also always staying in touch with our scouts and Mike Coflin,” Sampson said. 

The process of scouting 

The scouting process for junior hockey is an art form; Coflin and Sampson are masters in their field. 

Players who pull on the Winterhawks jersey don’t do so by accident. Hard work and dedication go into finding not only the best hockey players but the best players to play the style Johnston wants to instill. 

Despite being part of the Canadian Hockey League, Portland places a strong emphasis on having U.S.-born players on its roster. 

“I think our system does allow for U.S. players to easily be slotted into draft positions on board because we have a formula that is effective at placing players regardless of where they are playing,” Sampson said. 

With the recently created WHL US Prospect Draft and every team having the opportunity to select two Americans before the usual WHL Prospects Draft, which includes Canadians as well, Sampson and Coflin’s job got a little trickier. 

“Mike (Coflin) is able to see players in person on both sides of the border quite frequently. I think as a collective staff, we are really effective at knowing where our guys would fit in overall,” Sampson said. “I certainly keep track of our Canadian prospects and have an idea where those players have come from relative to those who we have from the United States. It is an inexact science, but there is definitely a lot of discussion between our staff, a lot of research and analysis, that whole matrix of information allows us to confidently place players using our formula in relation to each other regardless if they are Canadian or American.” 

Sampson’s lawyer background comes in handy when he’s spending a full day or weekend in bantam hockey rinks. 

“You may be in a rink for 10, 12, or more hours per day trying to track 100 plus players all the while you are trying to get a sense of where they potentially fit within a draft plan or within your team; that is no easy task. There is just so much information coming at you. My ability to take notes, distill stuff down, and then build a coherent report after an event where you are overwhelmed with a lot of information is something I’ve brought with me,” he said. 

Just because Portland does not elect to draft a certain player does not mean they will not circle back. 

Braeden Jockims and Luca Cagnoni are two current examples of players who were not selected in the WHL Prospects Draft but are key members of the organization. 

Luca Cagnoni (Photo: Keith Dwiggins)

“We really take pride in our ability to list players effectively, and you are seeing the results of that this year,” Sampson shared. “We kind of have to balance our time effectively between two ideals. Listing is so important to teams now. Every draft has those types of players. Someone can fall through the cracks, or maybe they are just a late developer or weren’t ready to play in this league at the time of their draft. They can really come into their own post-draft, so there are always going to be opportunities for those types of players. It requires a lot of attention and a lot of extra work, communication, and doing our research to find the types of players we’ve listed over the years.” 

Communication is a buzzword constantly thrown around in the workplace, and the scouting office of the Winterhawks is no exception. 

Sampson explained, “There is a lot of communication between the three of us (Johnston, Coflin, and Sampson) to make sure we are all on the same page. We have landmarks throughout the season. By December we have a preliminary list developed. We are confident in that list. How does that list change as we roll into January and beyond? Then those conversations as a complete staff with all our scouts and hockey operations, those become more and more frequent as we lead up to the drafts.” 

Greg Sampson and Mike Coflin (Photo: winterhawks.com)

Sampson’s previous work experience continues to pay off in his new position. 

“As a lawyer, you live and die by communication. Your ability to communicate effectively with clients or other lawyers, a judge in many cases, it involves a lot of listening,” he said. “So when you are speaking with a player or his family, it is important to have an understanding of what is important to them and that player’s future path in what they are looking for. I try to develop a pretty good understanding while also communicating what we are looking for. We help develop players and help them achieve their goals, whether that is playing hockey professionally or moving on to academics.” 

Away from it all

Working in sports means you will not work the nine-to-five job and have weekends off, so finding downtime is critical in preserving your sanity. 

“I’m big into music, and I’m very fortunate to be here in Portland where there is a great music scene,” Sampson said. “I still play guitar fairly often when I get the time.” 

The former lawyer will play anything from folk to blues to indie rock; you name it, he will play it. 

“I still also like to stay in touch and on top of the legal profession. I stay up to date on current events within the legal world but more specifically, sports law. It also sounds kind of crazy, but I still like to play some hockey to relax. It also helps me feel connected to the game in a sense. I do it for the exercise and to stay humble as I play with former Winterhawk Paul Gaustad’s group which has some great skaters. Getting outside to do a lot of dog walking too, rounds out my outlets.” 

Sampson took a gamble, bet on himself, made the move across the continent, and is enjoying every aspect of his new life. 

“Ultimately, to leave the legal profession at a time when I was starting to see some tangible results, that wasn’t an easy decision to not just walk away but take a side-lateral step into the hockey world. After speaking with Mike (Johnston) extensively and seeing what we are all about in Portland on the ground now, I know I made the right decision,” he said. 

However, Sampson’s greatest reward is seeing how hard work translates into success in games. 

“I see what goes into everything from our players and coaching staff. I get to see day-by-day how much work is going into everyone’s individual success and success as a team as well. Watching that process is so rewarding to me. Knowing how hard these guys work, our entire organization’s staff works, and seeing that translate into success on the ice and in the stands is amazing to me.”

Greg Sampson (Photo: winterhawks.com)

Johnston has seen Sampson take tremendous strides professionally since he landed in Portland. “He’s like one of your talented players that you can use on the power play, penalty kill, or late-game situations. Greg can do a little bit of everything, and he initiates, which is a great skill set. He’s got a great attitude, a hard worker, and I hope we can keep him for another three years.” 

Johnston knows bigger opportunities are going to come knocking soon for Sampson. 

“He is one of those guys within an organization you know isn’t going to be here very long. He will move up for sure in the next couple of years,” Johnston said. 

“I think he’s content right now to learn so that when he does move up, he’s prepared. There are a lot of different avenues for him, whether he wants to be on the cap side of the NHL, the management side, the marketing side, work directly with agents, etc. You can get different skill sets working here as it really helps you for the next level.” 

Sampson has absorbed everything like a sponge as he keeps his eye on his long-term goals. 

“Basically every day, under Mike’s (Johnston) tutelage, it is kind of a Masterclass in leadership, is the best way I can phrase it. I’ve been able to embrace the culture here too. It is an overused term in sports these days, certainly. If you look at the embodiment of positive organizational culture, it is here in Portland. That goes from ticketing, marketing, billets, education, you name it, all the way through the organization. I see that tie into the team’s success on and off the ice. That is probably the biggest reason I came here, and probably the most positive thing I’ll take with me wherever I end up in hockey or otherwise is how positively it all comes together here in Portland.” 

Sampson’s final comments are to take that risk or gamble. 

“If you are trying to get into something like sports, I know firsthand how frustrating and sole crushing an experience it can be in many regards. You have to stay persistent and have to certainly stay flexible. I’m a good example of that as I left my legal career and traveled several thousands of miles across the continent to pursue that. I think you have to remain open and kind of bet on yourself if you think you have the skillset and mindset to be successful.” 

“I’m here and I couldn’t be more thrilled to be here. I think I’m exactly where I need to be in the moment and a proud member of this exceptional organization.” 

Josh is the founder of PNW Hockey Talk and covers the Portland Winterhawks. His hockey background includes high school hockey in Minnesota. He followed Minnesota High School hockey and the NCAA prior to moving to Portland in 2015. The 2023-2024 season is his sixth year covering the Winterhawks.