Sid the Kid Crosby was selected first in the 2005 NHL Draft by the Pittsburgh Penguins. of the greatest hockey players of all time Crosby's resume with the Penguins includes being the youngest player to reach 100 points in single NHL season Art Ross Trophy winner youngest player to win scoring title in any North American sports league and Lester B. Pearson Award winner.In the 2008-09 NHL Stanley Cup Finals Sidney Crosby led the Penguins in Finals rematch against the Detroit Red Wings. Just one year prior the Penguins fell to Detroit. Crosby made sure Pittsburgh had their revenge becoming the youngest captain to ever win the Stanley Cup. Shop the iconic Crosby 2008-09 Blue Line Jersey. 100% Polyester.