Conn Smythe Trophy in the context of "Anaheim Ducks"

Sidney Patrick Crosby OC ONS (born August 7, 1987) is a Canadian professional ice hockey centre and captain of the Pittsburgh Penguins of the National Hockey League (NHL). Nicknamed "Sid the Kid" and dubbed "The Next One", he was selected first overall by the Penguins in the 2005 NHL entry draft. Born and raised in Halifax, Crosby was one of the most lauded prospects in ice hockey history and is widely regarded as one of the greatest ice hockey players of all time.

During his two-year major junior career with the Rimouski Océanic, he earned many awards and led his club to the 2005 Memorial Cup final. Océanic and the Quebec Major Junior Hockey League retired Crosby's jersey number 87 in 2019, and the QMJHL began presenting their Rookie of the Year award as the “Sidney Crosby Trophy” in 2025. Crosby debuted in the NHL during the 2005–06 season, recording 102 points and finishing as runner-up for the Calder Memorial Trophy as the NHL Rookie of the Year. At 18 years and 253 days, he is the youngest player to date to reach 100 points in an NHL season. By his second season, he led the NHL with 120 points to capture the Art Ross Trophy, becoming the youngest player and the only teenager to win a scoring title in any major North American sports league. That same season, Crosby won the Hart Memorial Trophy as the league's most valuable player (MVP) and the Lester B. Pearson Award for most outstanding player as judged by his peers. He started the 2007–08 season with the team's captaincy and subsequently led them to the 2008 Stanley Cup Finals, where they were defeated by the Detroit Red Wings in six games. The Penguins returned to the Finals against Detroit the following year and won in seven games; Crosby became the youngest captain in NHL history to win the Stanley Cup. Crosby also led Pittsburgh to Stanley Cup championships in 2016 and 2017, becoming the third player to win the Conn Smythe Trophy (playoff MVP) in consecutive years.

The 2008 Stanley Cup Final was the championship series of the National Hockey League's (NHL) 2007–08 season, and the culmination of the 2008 Stanley Cup playoffs. It was contested between the Western Conference champion Detroit Red Wings and the Eastern Conference champion Pittsburgh Penguins. This was Detroit's 23rd appearance in the Finals, and its first since winning the Cup in 2002. This was Pittsburgh's third appearance in the Finals, and its first since winning consecutive Cup championships in 1991 and 1992. The Red Wings defeated the Penguins in six games to win their eleventh Stanley Cup title. Detroit's Henrik Zetterberg was awarded the Conn Smythe Trophy as the Most Valuable Player of the playoffs. As of 2025, this is the most recent major professional sports championship won by a Detroit-based team.

This was also the first Cup Finals between two United States–based NHL teams since 2003.