Born: Aug. 7, 1987 (Halifax, Nova Scotia, Canada)
Position: Center
Career: Pittsburgh Penguins (2005-present)
Career highlights: Three-time Stanley Cup champion (2009, 2016, 2017), two-time Hart Trophy winner (2007, 2014), eight-time NHL All-Star (2007-09, 2011, 2015, 2017-19), two-time Ross Trophy winner (2007, 2014), NHL All-Rookie Team (2006), two-time Conn Smythe Trophy winner (2016, 2017), NHL All-Star MVP (2019)
Bottom line: As Sidney Crosby enters the twilight of his career, he’s still serving players a decade or more younger than him and still one of the NHL’s best players.
The oldest player on this list by almost five years, Crosby is already minted as one of the NHL’s greatest players of all time and can only burgeon his legacy in the coming years. You know what would be cool? While individual awards may be slightly out of his grasp at this point, a fourth Stanley Cup title to cap off his career would be a fitting final chapter … although the Penguins haven’t made it past the first round since the last time they won the Stanley Cup in 2017.