The Tampa Bay Lightning remain in win-now mode, but they are at the tail end of their win-now window. They have won two Stanley Cups since 2020 and reached three Stanley Cup Finals.

This season is particularly fascinating for the Lightning’s future, as they enter it with their top player less than 12 months away from unrestricted free agency. Nikita Kucherov is in the final year of an eight-year, $76MM contract that has been an absolute steal at $9.5MM per season.

Normally, this would be an open-and-shut negotiation for a franchise player coming off a 44-goal, 130-point, Hart Trophy-winning season, but Kucherov will be 34 next June, and the Lightning will likely not be competitive for the duration of his next contract, creating an interesting wrinkle in the negotiations. The Lightning want to keep Kucherov in Tampa Bay, and he probably wants to stay, but it’s not that simple.

Kucherov is still one of the best players in the game and hasn’t shown signs of slowing down. He is clearly worth a massive extension, and Tampa Bay doesn’t appear to have an issue giving it to him, as they have stated a desire to keep him in the fold.

The issue could lie in the next era of Lightning hockey and how much of a nostalgia act they are comfortable running before they pivot into that era.

Tampa Bay’s issue is a timeline problem, one that other teams