Maxim Tsyplakov
While he's aged out of being a prospect, Maxim Tsyplakov could be a player worthy of being given a chance in the NHL. At 25 years-old, Tsyplakov has been playing professionally in Russia (KHL) since as early as the 2017-18 season. This year has been his best in the KHL, exploding for 31 goals and 47 points in 65 games with Spartak Moskva.
The 6'3 winger is in the final year of his KHL contract and already has interest from NHL teams. He plays a hard-nose style game with the knack for scoring goals. If put with the right linemates, he could find himself in a middle-six role as a power-forward in the NHL.
It has been reported that 12 teams have already reached out to Tsyplakov about coming over to the NHL after his contract in the KHL expires.
The Blackhawks have current ties to the KHL in their system, with 2021 6th round pick Ilya Safonov and 2023 2nd round pick Roman Kantserov both playing in Russia. It was also known that Kyle Davidson had reached out to Calgary Flames forward Andrei Kuzmenko before he came over and signed with Vancouver.
A player like Tsyplakov could bring a good combination of size and skill to the Blackhawks roster as the opportunity for a larger role will be more wide open than it would be with other NHL teams. The Blackhawks don't have many power-forwards on the roster, but Tsyplakov has the potential to fill that role. His checking style of game on paper also sounds like it would fit in well with Luke Richardson's coaching. While he is not the youngest player on this list, Tsyplakov is nearing the prime of his career and could be a valuable asset to the Blackhawks.