While active player career earnings are led by megastars making massive salaries like Connor McDavid, when accounting for overall career wealth, endorsement portfolios, and long-term investments, Sidney Crosby and Alex Ovechkin historically rank among the wealthiest. However, looking at lifetime career earnings from contracts alone, Connor McDavid and other recent max-contract signees have accumulated staggering fortunes. Furthermore, retired legends like Wayne Gretzky and Mario Lemieux possess massive net worths built through lucrative business ventures, ownership stakes, and historical endorsements that far exceed any current active player's baseline salary. Mario Lemieux's previous ownership stake in the Pittsburgh Penguins, in particular, cemented his financial standing at the pinnacle of hockey wealth, making him significantly wealthier than any player currently lacing up skates in the league.