3 Personal Milestones Sidney C...

Sidney Crosby has been with the Pittsburgh Penguins since they drafted him on July 30, 2005. In 20 seasons, the longest-serving captain in team history is on the verge of scoring his 600th goal and 1,600th point early in the 2024-25 campaign.

However, heading into training camp, Crosby has yet to sign an extension despite being eligible since July 1. Supposedly, it's up to him whether or not he sees his future in Pittsburgh, and he's the one holding up the negotiations.

Fans hope Crosby will retire as a Penguin like his mentor Mario Lemieux, who spent his entire career in Western Pennsylvania. So, with that in mind, here are three things Crosby needs to achieve before he leaves Pittsburgh or retires.

#3. Score on a Penalty Shot

With 592 career goals, Crosby has scored against all 31 NHL teams. He's registered 16 hat tricks and has a playoff overtime goal on his resume.

As the Penguins' all-time leader in even strength, overtime, and game-winning goals, it is surprising that Sid the Kid has never scored on a penalty shot.

Thus far, Crosby is 0-for-5 in the one-on-one situation.

1. Dec. 8, 2007, vs. Roberto Luongo (@Vancouver)

2. Jan. 18, 2009, vs. Henrik Lundqvist (New York Rangers)

3. Nov. 27, 2010, vs. Miikka Kiprusoff (Calgary)

4. Jan. 5, 2014, vs. Al Montoya (Winnipeg)

5. Apr. 17, 2024, vs. Ilya Sorokin (@New York Islanders)

Interestingly, Evgeni Malkin is the only other player who ranks in the top five for goals in Penguins history without a penalty shot goal. Lemieux (first) was 6-for-8, Jaromir Jagr (third) was 1-for-3, and Jean Pronovost (fifth) was 1-for-1.

#2. Score a Game-Winner Against All 31 Teams

Lemieux is Pittsburgh's all-time leading goal with 690 lamplighters. During his career, he played against 29 clubs, scoring against 27 of them. Moreover, he tallied at least one game-winner against 25 of them.

Heading into his 20th campaign, Crosby has scored a goal against all 31 NHL teams and has a game-winner against 26. Considering he has 90 for his career, he trails only recently retired Jeff Carter (92) and Alex Ovechkin (129) for the most in the salary cap era.

To complete this milestone, Crosby needs to score the decisive goal against the St. Louis Blues, Anaheim Ducks, Los Angeles Kings, San Jose Sharks, and Vegas Golden Knights.

#1. Hoist the Stanley Cup at PPG Paints Arena

The Penguins have won the Stanley Cup on five occasions. The franchise lost only once when it advanced to the finals. That defeat occurred in 2008 when the Detroit Red Wings celebrated on Mellon Arena ice.

Meanwhile, Pittsburgh's five title wins took place on the road in Minnesota, Chicago, Detroit, San Jose, and Nashville.

None of those championship teams celebrated in front of the hometown crowd, meaning Crosby has a chance to do something never done before by securing a Stanley Cup win on home ice.

However, completing this task is easier said than done since the Stanley Cup has been celebrated on home ice just eight times in the salary cap, compared to 11 times on the road.