Sidney Crosby (Pittsburgh Penguins) NHL 7" Figure McFarlane's SportsPicks. Sidney Crosby was the #1 pick in the 2005 NHL Draft where he led the NHL with 120 points to capture the Art Ross Trophy, becoming the youngest player to win a scoring title in any major North American sports league. He has led the team to three Stanley Cup championships, becoming the third player to win the Conn Smythe Trophy in consecutive years and the youngest captain in NHL history to win the Stanley Cup. Crosby has won the Hart Memorial Trophy as league MVP twice, the Lester B. Pearson Award/ Ted Lindsay Award for most outstanding player as judged by his peers three times, Mark Messier Leadership Award twice, and earned the Art Ross Trophy twice. Crosby holds numerous records including youngest player to be named to the first All-Star team, youngest player to date to reach 100 points in an NHL season, and youngest player to record 200 career points.