Sidney Crosby: A Legendary Journey Through 21 Seasons with the Penguins

It’s hard to fathom that Sidney Crosby, the captain of the Pittsburgh Penguins, is celebrating 21 seasons in the NHL. This remarkable journey began exactly 21 years ago, on July 30, 2005, when the Penguins made him the first overall pick in the NHL Entry Draft. Dubbed “The Next One,” Crosby’s arrival in Pittsburgh was a pivotal moment in the franchise’s history, marking a new era that would see him succeed the legendary Mario Lemieux, who even played alongside him during part of his rookie season.

Since that fateful day, Crosby has led the Penguins to significant achievements, including Stanley Cup championships in 2009, 2016, and 2017. His impressive resume also boasts three Olympic medals—two of them gold—along with victories in the World Championship, World Cup, and 4 Nations Face-off. Individually, he has claimed two Hart trophies, two Art Ross Trophies, two Conn Smythe trophies, two Maurice “Rocket” Richard trophies, and three Ted Lindsay Awards.

Recently, Crosby made headlines by clinching his 21st consecutive season averaging over a point per game, breaking a record he previously set after eclipsing Wayne Gretzky’s mark the season prior. This milestone further solidifies his status as one of the greatest players in hockey history.

Currently, Crosby is widely regarded as a top-10 all-time NHL player, with many placing him firmly in the top five. As he stands seventh on the all-time scoring list, he surpassed Lemieux to take the franchise lead in points during the 2025-26 season. Projections indicate that he will soon surpass Ron Francis, who sits at 1,798 points, potentially placing him among the top five scorers in NHL history.

With the possibility of reaching the coveted 2,000-point milestone, Crosby could become only the second player in NHL history to achieve this feat. If he continues on this trajectory, the debate over who ranks above him in all-time greatness may shrink to just one or two names.

However, where does Crosby currently stand among his younger counterparts? Elite Prospects has him ranked No. 12 among active players, with the next oldest player in the top-25 being goaltender Connor Hellebuyck at age 33. THN echoes this sentiment, also ranking Crosby at No. 12. In EA’s NHL 26, he received the eighth-highest player rating, a 94, trailing only Connor McDavid.

Last season, Crosby finished No. 22 in the league for points per game with an impressive 1.088. The only player older than him who ranked higher was his teammate Evgeni Malkin, who was just ahead at No. 21 (1.089). Among players aged 30 or older, only seven made it into the top-25.

As he heads into his age-39 season, Crosby’s performance remains exceptional, especially considering there are few players his age competing at a similar level. Although he did face a setback due to a knee injury while captaining Team Canada at the 2026 Olympic Winter Games, causing him to miss 14 games, questions about his elite status are unfounded.

Reflecting on the moment he donned the Penguins’ gold jersey 21 years ago, the 18-year-old from Cole Harbour, Nova Scotia, could hardly have imagined the incredible legacy he would build. As his story continues to unfold, there’s little doubt that Crosby will be remembered as one of the top three players in hockey history when he eventually hangs up his skates.

Note: This recap is an independently written summary based on publicly available reporting.