3 reasons why Sidney Crosby should actively pursue a trade out of Pittsburgh

Sidney Crosby has played with the Pittsburgh Penguins since he was 18. He's won three Stanley Cup titles and ranks behind franchise icon Mario Lemieux in almost every statistical category, building his case as one of the NHL's all-time greats.

However, after qualifying for the playoffs for 16 consecutive seasons, the Penguins missed out last season by a single point and have fallen further behind in 2023-24. Unless they pull off a miracle, Pittsburgh will most likely miss the playoff cut-off by seven or eight points.

After general manager Kyle Dubas dealt away one of his best players, pending unrestricted free agent Jake Guentzel, at the NHL trade deadline, it appears the Penguins are about to face the harsh reality that they will need to rebuild or retool, which will occur during Crosby's final seasons.

So, at 36 and still producing at a point-per-game pace, thanks to 65 points in 65 games, what does the future hold for the Penguins captain, and does he finish his career in Pittsburgh?

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3 reasons why Sidney Crosby should actively pursue a trade out of Pittsburgh

#1. The Penguins could see an entire coaching staff shuffle

Mike Sullivan has been behind the bench with the Penguins since the 2015-16 season, becoming the franchise's longest-tenured and winningest head coach.

Capturing two Stanley Cup championships during his first two seasons and a lengthy playoff streak allowed him a lot of leeway, which explains why he's still in his position almost a decade later.

Mike Sullivan, Pittsburgh Penguins, Pittsburgh Penguins, 2017 NHL Stanley Cup Final

Despite those accomplishments, he's still the man whose voice and strategy lead to wins and losses. However, many of the Penguins' current struggles are pinned on him and former general manager Ron Hextall.

By pushing Pittsburgh against the salary cap ceiling and signing older, veteran, unproductive players like Jeff Carter, Hextall had hoped to catch lightning in a bottle. However, this did not occur during his tenure, which ended in the summer of 2023.

Although not all the fault can be placed on Sullivan, it seems that his tenure is about to end with two consecutive seasons without postseason participation. Ultimately, this leads back to Crosby, who may enjoy working with Sullivan or be one of the voices who wishes for a new coach to write a winning game plan.

Either way, change is coming to the Penguins organization and will mark the first time in a long time that the team's longest-tenured player will have to adapt his game around someone else drawing up the plays.

#2. A strong supporting cast no longer surrounds Crosby

As mentioned, Crosby's good friend Guentzel is gone, and so are the 22 goals and 52 points he had in the 2023-24 season. After 65 games, Crosby leads the team in scoring 32 goals and 65 points, with long-time teammate Evgeni Malkin ranking second with 50 points.

Heading into the season, the Penguins were the oldest team in the NHL. After the trade deadline, they are the fourth oldest, with an average age of 27.89. Their elder statesmen include Carter (39), Malkin (37), Crosby (36) and Kris Letang (36).

Thus far, 35 players have played a game with Pittsburgh this season, with 22 aged 30 or under. However, Guentzel was the top player in that group, collecting 52 points, with the next highest scorer under 30 being defenseman Marcus Pettersson, who scored 24 points.

Jake Guentzel, Evgeni Malkin and Sidney Crosby of the Pittsburgh Penguins

In the season's final 17 games, Malkin (19) and Bryan Rust (19) have a chance to score 20 goals, but with Guentzel off the books now, the Penguins will finish with the fewest 20-goal scorers (three) in four seasons.

As it stands, Pittsburgh ranks 25th overall in NHL scoring with 187 goals, which is another testament that once hailed as the league's most lethal offense, it has lost a step since winning back-to-back titles.

#3. Crosby may want other opportunities to check off a few bucket list items

Crosby grew up in Halifax, Nova Scotia, rooting for the Montreal Canadiens, the team that drafted his father, Troy, in 1984. Although he never cracked an NHL lineup as a goalie, the family has had strong ties with the Original Six franchise.

Despite all his accomplishments and community involvement in Pittsburgh, Crosby may desire an opportunity to skate for his childhood team and play with one of the most iconic franchises in professional sports.

On the other hand, he's close to Colorado Avalanche star Nathan MacKinnon, who is about to win the Art Ross Trophy for the first time with a league-leading 115 points.

The Avalanche won the Stanley Cup in 2022 and are close to recapturing the silver chalice again in 2024. A tandem with MacKinnon would give them an even better shot in 2025 or 2026.

Finally, although their respective clubs are bitter rivals on the ice, Crosby is also close to Brad Marchand, captain of the Boston Bruins. As another Nova Scotia native, Crosby's possible link-up with David Pastrnak would give the Bruins, another Original Six franchise, an unfair advantage and increase their championship aspirations.

Even though he will likely end his career with the Penguins, he may not want to be part of a deep rebuild that will result in top draft choices in the coming years. If he decided to pursue opportunities outside of Steel City, 31 other teams would be willing to move mountains to acquire him, even if only for half a season.

As mentioned, Crosby will be considered one of the all-time greats, with one of the most distinguished resumes in hockey history. At this point, it would be unfair for him to play on a struggling team to end his career, but he'll have to consider whether that is an option in the weeks and months leading up to his retirement.