Todd Diamond is one of the most prolific player agents in the National Hockey League, with a client list that includes Florida Panthers captain Aleksander Barkov, Carolina Hurricanes forward Andrei Svechnikov, and St. Louis Blues forward Pavel Buchnevich.

This off-season has been a busy one for Diamond, as he saw three of his clients - Ivan Provorov (seven years, $59.5M), Mikael Granlund (three years, $21M), and Dmitry Orlov (two years, $13M) - sign high AAV contracts as unrestricted free agents.

With the NHL salary cap set to make a significant jump over the next three seasons, some teams made large financial commitments, while other clubs were able to retain talent with significant hometown discounts.

Speaking to TSN Radio, Diamond discussed the process he goes through with his clients when balancing a preferred landing spot against a bigger contract.

“It's very hard to buy happiness. You can get a nice, big contract on July 1, move to a new location and upend everything in your life. If the player has a family, it upends the family's life too, and a lot of the time it doesn't work out,” Diamond said. “If there's a fit, a history with the organization, whether he's close to his teammates and the coaching staff and ownership, then usually you can try to work something out.

“Looking at the hometown discounts. Living where the Florida Panthers are playing, that's a very unique situation where those players have a really special thing going and the opportunity to do something that hasn't been done in a long time. It's a very tight group.”

The reigning back-to-back Stanley Cup champion Panthers made waves this off-season as general manager Bill Zito was able to retain all three of his unrestricted free agents - Conn Smythe winner Sam Bennett, Aaron Ekblad, and Brad Marchand - to contracts that were perceived to be under market value.

The contracts reignited the debate that NHL teams from no-income tax states have a competitive advantage over the rest of the league, as five of the past six Stanley Cup winners have come from no-tax states.

However, Diamond believes the organizational makeup of a franchise plays a bigger role when players choose their next destination.

"I think it's a red herring. It's all about winning and how organizations are treating players,” said Diamond. “Obviously, lifestyle, weather and climate play a role to a certain extent, but I don't think it's just a state tax issue at the end of the day.

“I've had players who are happy to re-sign in Pittsburgh or Carolina. It really doesn't matter. It's all about the feel and the ability for organizations to compete that are the foremost drivers in players deciding where they want to play.”

Gavin McKenna, the projected No. 1 pick in the 2026 NHL Draft, announced on Tuesday that he had committed to playing in the NCAA next season at Penn State, leaving the Western Hockey League’s Medicine Hat Tigers.

While the move has sparked debate about the future of the Canadian Hockey League, Diamond doesn’t believe McKenna’s move is the end of the CHL as we know it. 

“The thing that drives [players] the most is playing the game. If I were a player going from playing 70 games in a really strong league to playing 35, that's a little strange to me,” Diamond said. “The whole landscape has changed in the NCAA with the money flowing into the programs and the ability to share it with the athletes.

“You speak to NHL teams, and they all teach development, development, development. I think that playing more meaningful games is important at that age. A player with Gavin McKenna's ability will be just fine. But I think if you see the money filtering down to players who maybe need a different approach, we'll see how it's going to work out.

“We're just in the early stages of players making that move, so we'll see how it goes.”