The Chicago Blackhawks have struggled since their last Stanley Cup triumph in 2015. This was in many ways expected; the Blackhawks had been going all in since 2009, and when you push that hard for that long, the chickens come home to roost eventually.
As a Penguins fan, I am worried they will take a Blackhawks-like trajectory. An aging core that traded away key young players and draft capital in order to maximize the twilight years of franchise legends.
The vibe in Chicago is uneasy, to say the least. Connor Bedard was visibly and vocally frustrated several times with the play of the Blackwaks this year. They eventually traded away Seth Jones to Florida at the deadline in exchange for draft capital and young goalie Spencer Knight. However, there is a young player on the Blackhawks who has an uncertain future.
Ryan Donato

In an effort to provide Connor Bedard with a wingman, the Blackhawks moved Ryan Donato up a couple of lines to play alongside the face of the franchise. It worked to an extent, especially for Donato, the 29-year-old winger had 62 points this year, evenly split between goals and assists.
The Penguins should immediately offer Donato a bag as soon as free agency opens. The 62 points were double Donato's career high. The question is, has Donato reached his peak or is he ascending? It is worth mentioning that he took off once he was placed on Bedards line.
Imagine pairing him with Sidney Crosby. Crosby is a significantly better player than Bedard so I think Donato can really shine next to Crosby. Dailyfaceoff projects him to get a 3X4.2 contract. That is a steal if you ask me. I would gladly offer him 5 million a year and give him four years. Plus, he can also play center. Once Malkin retires, Donato can slide into that 2C role.