In the more than 100 years that the National Hockey League has existed, there have not been many better players to hit the ice than Sidney Crosby. The already Hall of Fame-bound Canadian superstar has dominated at every level and brought the momentum to the then-dying Pittsburgh Penguins. He not only helped put the team, owned by the legendary Mario Lemieux, back on its feet but Sid the Kid also brought the Stanley Cup back to the Steel City.

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Throughout the 15 years of an exceptionally successful NHL career, he has played with many great players. Crosby is one of the few who makes his teammates better and helps them develop. However, some wingers have fit his style better than others. Who are the top 5?

5. Conor Sheary

Sheary’s journey to the NHL sounds like an American dream. The 5-foot-8 American was undrafted, yet didn’t give up on his ultimate goal. After spending time with the Wilkes-Barre/Scranton Penguins, he eventually got the opportunity to show his skills in the world’s best league. Not only that but in the following season, he was placed on a line with arguably the best player in the world.

In the middle of the 2015-16 season, it seemed like Crosby was on pace for about 40 points and the Penguins were going to miss the playoffs. Luckily, new head coach Mike Sullivan put young Sheary on Crosby’s top-line.  Their chemistry started clicking and the Penguins captain finished second in Hart Trophy voting behind Patrick Kane. And Sheary? He registered 23 goals and 30 assists in just 61 games. Sullivan kept the duo together for the playoffs, which brought them the Stanley Cup.

4. Mark Recchi

Back in the 2005-06 season, Crosby entered the league as ‘The Next One.’ That is a lot of pressure for an 18-year-old. To adjust properly to such a demanding environment both on and off the ice, a couple of veteran players helped Crosby out. One of them was Mark Recchi.

No. 87 spent a lot of time on the ice with the future Hall of Famer, Recchi, which was crucial to his career. The duo played a lot together during Crosby’s first two seasons, as the young prodigy took the league by storm putting up 75 goals and 222 points. During that time, Recchi registered 48 goals and 125 points.

3. Pascal Dupuis

Some players simply need more time to develop. Dupuis was undrafted as well and earned a spot with the Minnesota Wild after five seasons in the Quebec Major Junior Hockey League. The late bloomer, was at the peak of his game in Pittsburgh.

His skating ability backed off defenders, and he backchecked like a madman when his line didn’t have the puck,

Jonathan Bombulie on Dupuis (from ‘Who has been Sidney Crosby’s top Penguins linemate? Chris Kunitz by a landslide,’ Trib Live, 07/31/2019).

The Canadian’s greatest asset was his versatility. He complemented the Penguins captain’s extraordinary vision with a solid slapshot and reliable back-checking. Dan Bylsma, the Penguins’ head coach at the time, said that Dupuis was the winger who could bring out the best in Crosby. With the Penguins, Dupuis totaled 109 goals and 247 points in 452 games and spent much of that time on Crosby’s wing.

2. Jake Guentzel

Jake Guentzel is possibly the most talented winger to have regularly played with the iconic captain. Along with Sheary, the trio created a line that fans called Sid and the Kids in the 2017 Stanley Cup Playoffs. Guentzel managed to net 13 goals and was among the hottest candidates to win the Conn Smythe Trophy.

No. 59 is excellent at positioning and making himself open to Crosby’s unexpected quick passes. He possesses a great shot and is also a very solid playmaker. In 243 regular-season games, he has 98 goals and 200 points. His most valuable asset is how he elevates his game in the postseason, where he has 43 points in 41 games. Guentzel is also the only player on this list who proved that he can score even without Crosby.

1. Chris Kunitz

Yet another player who slipped through the draft unnoticed, Kunitz had all the tools Crosby needed from a winger. The four-time Stanley Cup champion wasn’t afraid to throw his body around, but at the same time, had a fine touch for scoring.

In the 2013-14 season, Kunitz was at the top of his career, registering 35 goals and 68 points. His chemistry with Crosby helped him make Team Canada’s star-stacked 2014 Olympic roster and win the Gold Medal. Crosby assisted on 83 of Kunitz’s goals with the organization, the most of all Penguins wingers. Thus, it is only fitting that Crosby recorded the 1,000th point of his career on Kunitz’s goal against the Winnipeg Jets on Feb. 16, 2017.

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On August 7, Crosby will turn 33. Even though he still is one of the best players in the league and an essential part of the Penguins organization, most of his career has already gone by. Thus, there are few players who can take Kunitz’s place as Crosby’s best winger in the future. Possibly, the only one that could do that is Guentzel. With a contract until the end of the 2023-24 season, the duo will have a lot of time to show what these two are capable of together.

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