Going back 20 years, ahead of the highly anticipated (at the time) 2005 NHL Entry Draft, everyone’s number one pick was a 17-year-old Sidney Crosby. The teenager was doing the rounds and meeting representatives of all 30 NHL franchises.
During a meeting with the New York Rangers, they asked a peculiar question, Crosby recalled in a USA Today interview in 2015.
Sidney Crosby’s Perfect and Prophetic Response to NY Rangers Question
The Rangers’ team posited a hypothetical scenario to Crosby:”‘If we could give you a pill that you could take that would guarantee that you would be part of a Stanley Cup-winning team and a Olympic gold medal team, but you couldn’t live past age 25, would you take that pill?”
Even 10 years after the incident, Crosby said he can still remember his thoughts at that exact moment.
“But it was such a weird question, and I remember thinking, ‘How do you answer that?'” he said via USA Today.
In hindsight, we can say that Crosby’s actual response to the question was a testament to his remarkable talent, confidence, and ability.
“I wouldn’t take the pill,” he had told the Rangers, “because I plan to win more than one of those.”
20 years on, Crosby has more than lived up to the assertion he made in that boardroom. He has three Stanley Cup wins (2009, 2016, 2017) with the Pittsburgh Penguins and two Olympic gold medals (2010, 2014). His host of individual trophies includes becoming a two-time Hart Memorial Trophy winner (league MVP) and two-time Art Ross Trophy winner (league scoring leader).
He also led Canada to win the 4 Nations Face-Off trophy in February 2025 and is set to captain his country for the 2026 Olympics as well.
Perhaps it’s just as well Crosby didn’t join the Rangers. The veteran NHL player, who has spent his entire career with the Pittsburgh Penguins, says it is “perfect” for him.
“I think New York is an awesome city. I have a good time there, but I couldn’t see myself living there. It’s so busy. It’s not what I’m used to,” Crosby said.
Crosby Broke Wayne Gretzky’s Record This Season
The 37-year-old Crosby has broken many records throughout his career. He became the youngest-ever captain in the league to win the Stanley Cup in 2009. Crosby also holds the record of being the youngest NHL player to reach 100 points in a season. His Art Ross Trophy in 2006-07 made him the only teenager in any major North American sports league who has earned an accolade for scoring.
This season, Crosby broke a record that was earlier held by fellow Canadian legend Wayne Gretzky. Crosby overtook “The Great One’s” record for most NHL seasons with a point-per-game average or higher. Showcasing his remarkable consistency, Crosby has maintained that average over 20 seasons, one more than Gretzky.
