1. Bobby Orr
"There's a reason they call it the Stanley Cup 'dream'. It's because every kid who's ever laced up a pair of skates has imagined himself hoisting it above his head, celebrating with his teammates."
- Bobby Orr is a two-time Stanley Cup Champion with the Boston Bruins (1970, 1972) and in both victories, he scored the clinching goal.
2. Mark Messier
"The Stanley Cup is more than just a trophy. It's a symbol of hockey's history and tradition. Every player who's ever held it knows they're a part of something bigger than themselves."
- Mark Messier is a six-time Stanley Cup champion — five with the Edmonton Oilers (1984, 1985, 1987, 1988, 1990) and one with the New York Rangers (1994) and is the only man to win NHL titles as captain of two different teams.
3. Scott Niedermayer
"The Stanley Cup is the holy grail of hockey. It's not just about winning games; it's about leaving a legacy that will be remembered for generations to come."
- Regarded as one of the greatest defencemen in NHL history, Scott Niedermayer is a four-time Stanley Cup Champion–three with the New Jersey Devils (1995, 2000, 2003) and one with the Anaheim Ducks (2007).
4. Wayne Gretzky
"There's nothing like winning the Stanley Cup. It's the ultimate achievement in hockey, and it's what every player dreams of from the moment they lace up their skates."
- Nicknamed “The Great One”, Wayne Gretzky captained and led the Edmonton Oilers to four Stanley Cup victories (1984, 1985, 1987, 1988).
5. Sidney Crosby
"The Stanley Cup isn't just a trophy; it's a symbol of sacrifice, determination, and teamwork. Winning it is a bond that lasts a lifetime."
- Sidney Crosby — dubbed “The Next One” — captained the Pittsburgh Penguins all the way to three Stanley Cup victories (2009, 2016, 2017).
6. Jonathan Toews
"You don't lift the Stanley Cup, you hug it. You embrace all the struggles, the sweat and the tears it took to get there. It's a feeling like no other."
- A member of the elite “Triple Gold Club”, Jonathan Toews is a three-time Stanley Cup Champion with the Chicago Blackhawks (2010, 2013, 2015).
7. Brad Marchand
“If you are not playing for the Stanley Cup at the end of the year, what's the point? If you don't win, you may as well not make the playoffs, because you are loser just like everyone else."
- Brad Marchand won his first, and only, Stanley Cup Champion during his rookie season with the Boston Bruins (2011).
8. Patrick Roy
“I didn't hear him because my two Stanley Cup rings were plugging my ears."
- Widely credited with popularizing the butterfly style of goaltending (and known for the cocky eye wink), Patrick Roy is a four-time Stanley Cup Champion, winning twice with the two teams he split his NHL career with — the Montreal Canadiens (1986, 1993) and Colorado Avalanche (1996, 2001).