Surprisingly there's no islands, every team has somehow had at least one player who's won it again, there's several close calls where the connection almost broke. A few times where a winner starts off as an island and then gets connected later on. Most recently St. Louis almost got marooned in 2019. Same thing happened before in '89, '80', '74, etc.
You can six degrees of Kevin Bacon anybody; just search a name and click 6-degree icon next to it to choose another. It takes 9 handshakes to go from the first cup to the last.
You can move between eras or set a specific range, search and select any player, team, or connection, recolour by dynasty, switch between a network view and a year-by-year timeline, filter by multi-Cup winners or player positions.
Nodes are draggable, selections can be isolated and cut as subgraphs, reset, or resized. Copy pastable urls to save or share what you're seeing and story mode where you can play back or forward the entire history.
Data reconciled from Wikipedia, NHL records, hockeydb, and other public sources. Repo is open-source, let me know if you find anything interesting.