Sidney Crosby

Crosby was born in the Grace Maternity Hospital in Halifax, Nova Scotia on August 7, 1987 to Troy and Trina (née Forbes) Crosby. Crosby's jersey number (87) and 2007 contract signing ($8.7 million per year) reflect his birthdate (8/7/87). Crosby grew up in nearby Cole Harbour and has a younger sister named Taylor. His father was a goaltender who played for the Verdun Junior Canadiens in the Quebec Major Junior Hockey League (QMJHL). Troy played in the 1985 Memorial Cup and had been drafted 240th overall by the Montreal Canadiens in 1984, but never played at the NHL level. Growing up, Crosby admired Steve Yzerman and, like his father, was a Canadiens fan. Crosby began playing hockey by himself in his basement at the age of two, shooting pucks in a net that had the family dryer behind it, leading to a longstanding misconception that he was actually practising with the dryer; he learned to skate at age three.

Early in his minor hockey years, Crosby began attracting media attention for his play and gave his first newspaper interview at age seven. When Crosby was 13, Nova Scotia's Minor Hockey Council refused to allow him to play midget, a level of minor hockey designated for 15- to 17-year-olds. His family sued but lost. The following year, he entered the midget level with the triple-A Dartmouth Subways and went on to score a combined 217 regular season and playoff points, leading Dartmouth to a second-place finish at the 2002 Air Canada Cup. He was named the MVP and Top Scorer awards at the national tournament at the tournament banquet held after the preliminary round and he finished the tournament with 24 points (11 goals and 13 assists) in 7 games. Crosby was called up as a 14-year-old to play two games with the Maritime Junior A Hockey League's Truro Bearcats that season. Crosby had been drafted by the Bearcats in the 2001 MJAHL Draft as a 13-year-old.

Crosby was selected first overall in the 2003 Midget Draft by the Rimouski Océanic of the Quebec Major Junior Hockey League (QMJHL). In his first exhibition game, he scored eight points, leading his teammates to nickname him "Darryl" (in reference to Darryl Sittler's ten-point NHL game in 1976). In his first regular season game in the QMJHL, he scored one goal and added two assists. He was named QMJHL Player of the Week for two consecutive weeks at the start of the season and won the honour four more times as the season progressed. He was named QMJHL Player of the Month and Canadian Hockey League (CHL) Player of the Week three times each. Crosby finished his rookie QMJHL season with 54 goals and 81 assists over 59 games to capture the Jean Béliveau Trophy as the league's leading point-scorer. He was further recognized with the RDS/JVC Trophy (overall rookie of the year) and Michel Brière Memorial Trophy (most valuable player), becoming the first QMJHL player to win all three major awards at once. Rounding out Crosby's accolades for the 2003–04 regular season were QMJHL All-Rookie and First All-Star Team honours, as well as Offensive Rookie, Offensive Player and Personality of the Year Awards. As a team, the Océanic led the Eastern Division with 34 wins and 76 points. After receiving a first-round bye in the 2003 QMJHL playoffs, they defeated the Shawinigan Cataractes in the quarterfinals, then were eliminated by the Moncton Wildcats in the semi-finals. Crosby recorded 16 points (7 goals and 9 assists) over 9 playoff games.

Crosby went on to compete in two World Junior Championships with Team Canada's under-20 team. When he was named to the team in December 2003, he became the fifth 16-year-old to represent Canada at the tournament, following Jay Bouwmeester, Jason Spezza, Eric Lindros and Wayne Gretzky. Competing in the 2004 World Junior Championships in Helsinki, he then became the youngest player to score a goal in the history of the tournament at 16 years, 4 months, and 21 days when he scored against Switzerland in a 7–2 win. This record would last until the 2012 World Juniors, when Aleksander Barkov of Finland scored a goal aged 16 years, 4 months. Crosby finished the tournament with two goals and three assists in six games, helping Canada to a silver medal finish. The following year, he returned for Canada at the 2005 World Junior Championships in Grand Forks, North Dakota. He improved to six goals and three assists as Canada earned gold. Crosby stated the following year that his most memorable hockey moment was winning his World Junior gold medal.

During the off-season, the World Hockey Association, a major professional league proposed to rival the NHL, held an Entry Draft on July 17, 2004. Holding the first overall selection, Toronto chose Crosby. The following month, it was reported that Crosby turned down a US$7.5 million contract over three years to play for Hamilton. Crosby told reporters that while "it took a lot to say no to that much money", he "work[ed] hard most of his life to play in the NHL". The contract would have paid him $2.5 million annually and an additional $2 million payout regardless of whether the WHA was realized as a legitimate league or not. However, it was not clarified, how Hamilton could have signed Crosby, as Toronto held his WHA playing rights. Nevertheless, the WHA never materialized.

From age 12 to 15, Crosby attended Astral Drive Junior High School. He was a straight-A student and, according to the vice-principal, "an amazing role model, who was really kind to students in the learning centre and to special needs kids". At age 15, Crosby transferred to Shattuck-Saint Mary's in Faribault, Minnesota, to play with the school's hockey program. While playing for the Rimouski Océanic of the QMJHL, Crosby attended and graduated in 2005 from Harrison Trimble High School, in Moncton, New Brunswick.

Entering the 2005 NHL Entry Draft, Crosby was listed first overall in the NHL Central Scouting Bureau and International Scouting Services' respective rankings of prospects. He had also won the Mike Bossy Trophy as the QMJHL's best prospect. Crosby went on to be selected first overall in the draft by the Pittsburgh Penguins on July 30, 2005. Due to the labour lockout that suspended the entire 2004–05 NHL season, positioning for the 2005 draft was conducted via a weighted lottery based on each team's playoff appearances and draft lottery victories in the last four years. This lottery system led to the draft being popularly referred to as the "Sidney Crosby Lottery" or the "Sidney Crosby Sweepstakes".

"Sid the Kid", a nickname given to him by the media early in his career, made his NHL debut on October 5, 2005, against the New Jersey Devils, and registered an assist on the team's first goal of the season, scored by Mark Recchi in a 5–1 loss. He scored his first NHL goal in the Penguins' home opener on October 8 against goaltender Hannu Toivonen of the Boston Bruins. Despite having registered two assists for a three-point night, the Penguins were defeated 7–6 in overtime. Crosby began his rookie season playing alongside Hall of Famer Mario Lemieux. Unfortunately, Lemieux was forced to retire due to an irregular heartbeat after having played just 26 games of the season. Near the midway point of the season, Penguins head coach Ed Olczyk was fired and replaced by Michel Therrien on December 15, 2005. The following day, Therrien designated Crosby as an alternate captain for the Penguins. The move drew criticism from some hockey pundits, including Don Cherry, who claimed that Crosby did not have the experience for the position. Cherry said, "An 18-year-old kid says he's going to give us ideas. What, from the Quebec League, he's going to give them ideas? Come on. That's ridiculous." Although hopes were high in Pittsburgh for the club to succeed, largely in part to the beginning of Crosby's NHL career and bolstered by the acquisitions of Sergei Gonchar, Žigmund Pálffy and Mark Recchi, the Penguins still finished with the worst record in the Eastern Conference.

Crosby's number 87 Pittsburgh Penguins jersey was the top seller on the NHL's website from September 2005 to February 2008. It has continued to be among the top-selling jerseys since his rookie season. In January 2005, an Air Canada baggage handler in Montreal stole Crosby's red Canada jersey from the World Junior Hockey Championship. It was recovered later in a mailbox. His white jersey from the tournament was temporarily delisted from an auction while the red one was missing. It eventually sold for $22,100, which went to youth hockey charities and 2004 Indian Ocean earthquake relief.

In his second NHL season, Crosby built on his rookie success. On October 28, 2006, Crosby scored his first NHL hat-trick in an 8–2 victory over the Philadelphia Flyers. His success against the Flyers continued as just over six weeks later, on December 13, he recorded the first six-point game of his career (one goal and five assists). The multi-point effort vaulted Crosby into the NHL scoring lead, which he would retain for the remainder of the season. He finished the 2006–07 with 36 goals and 84 assists in 79 games to become the first teenager to lead the NHL in scoring since Wayne Gretzky in 1980. Being only 19 years old at the time, he became the youngest player in NHL history to win the Art Ross Trophy and the youngest scoring champion in any major North American professional sport.

After completing his rookie season with the Pittsburgh Penguins, Crosby competed in the 2006 IIHF World Championship as an alternate captain for Canada. Scoring a tournament-best eight goals and eight assists in nine games, he became the youngest player ever to win a World Championship scoring title. Despite his performance, Canada failed to medal, being shut-out by Finland 5–0 in the bronze medal game. Crosby was named the tournament's top forward and to the competition's all-star team.

After omitted from Canada's Olympic team in 2006, Crosby was named to the Canadian roster on December 30, 2009, as an alternate captain for the 2010 Winter Olympics in Vancouver. He scored the game-winning shootout goal for Canada in the second game of the preliminary round against Switzerland. After going pointless in the quarter- and semi-final against Russia and Slovakia respectively, Crosby scored the winning goal 7 minutes and 40 seconds into overtime against the United States in the gold medal game. The goal has later become known as the "Golden Goal" due to it being scored in the gold medal game. It is also regarded by some as "Canada's most iconic sports moment".

Crosby rarely discusses his personal life and avoids social media. Andy O'Brien, Crosby's fitness trainer for over 15 years, has said: "He [Crosby] wants to be one of the guys and doesn't really seek to separate himself or get special treatment in any way... He takes a lot of enjoyment in the regular, simple things in life and having a normal, ordinary routine". Greg Powers described Crosby as essentially the brother of Lemieux's son Austin, as he lived with Lemieux's family in Sewickley, Pennsylvania, from 2005 until 2010. In the spring of 2010, Crosby purchased his own home in the same area. In June 2006, he bought his first house on Grand Lake in Halifax, Nova Scotia.

Crosby's second NHL season also saw significant improvements for the Penguins franchise as a whole, as the emergence of Calder Trophy-winner Evgeni Malkin and runner-up Jordan Staal complemented the club's offence. As a result, the Penguins jumped from last place in the Eastern Conference the previous season to fifth for the club's first playoff appearance since 2001. Playing the Ottawa Senators in the opening round, Crosby scored a goal in his Stanley Cup playoff debut in a 6–3 loss. He finished the series with five points in five games as the Penguins were ousted by the eventual Stanley Cup runner-up. Following the Penguins defeat, Crosby was named Pittsburgh's team captain on May 31, 2007, making him (at 19 years, 9 months, and 24 days) the youngest team captain in NHL history. During the season, the Penguins had offered him the captaincy, but he had turned it down. In the press conference naming him the team captain, he explained:

At the NHL's annual awards show later in June 2007, Crosby completed a rare off-season "hat-trick", winning the Hart Memorial Trophy and the Lester B. Pearson Award in addition to his previously-clinched Art Ross Trophy. He became the youngest player in NHL history to win the Lester B. Pearson, and only the second youngest player ever to win the Hart (after Gretzky). He became the youngest player ever to be named to the NHL's First All-Star Team.

With Crosby's initial three-year, entry-level contract set to expire at the end of the following season, the Penguins signed him to a five-year, $43.5 million contract extension on July 10, 2007, ensuring his stay with the Penguins through the 2012–13 season. Midway through the subsequent season, Crosby recorded a Gordie Howe hat-trick on December 20, 2007, in a game against the Boston Bruins. His first assist came 55 seconds into the first period. At 8:26 of the same period, Crosby scored to give the Penguins a 2–0 lead. Then, five minutes and nine seconds into the second frame, Crosby fought ex-Penguin defenceman Andrew Ference to complete the hat-trick. This was Crosby's first NHL fight. In NHL's first Winter Classic (with a record crowd of 71,217 fans in attendance), Crosby scored the shootout winner in heavy snowfall to defeat the Buffalo Sabres. However, two weeks later, on January 18, 2008, Crosby suffered a high ankle sprain crashing leg-first into the boards in a game against the Tampa Bay Lightning. As a result, he missed the 2008 All-Star Game, to which he was named a starter. After missing 21 games, he returned on March 4 against the Lightning and earned an assist. However, two games after his return, he felt his ankle was not up to shape and decided that he needed more time for it to heal. Crosby consequently sat out of the Penguins' next seven games and returned on March 27, 2008, to help the Penguins defeat the New York Islanders 3–1. Despite his injury-shortened campaign, Crosby still managed 72 points in just 53 games.

In the 2009–10 NHL season, Crosby tied Tampa Bay Lightning centre Steven Stamkos for the lead in goals scored, with 51 goals, earning the Rocket Richard Trophy. He also garnered 58 assists for a total of 109 points, enough to tie with Alexander Ovechkin for second in league points, trailing only the Vancouver Canucks' Henrik Sedin's 112. Crosby was also named a finalist for the Hart Memorial Trophy and Ted Lindsay Award. Crosby won the Mark Messier Leadership Award, getting recognized as a "superior leader within the sport, setting a positive example through on-ice performance, motivation of team members and a dedication to the community". This was the second time he had received this honour, the other being in January 2007, during the award's first year when it was presented monthly. He was also included on NHL's all-decade second team of 2000s.

Early in the following season, on October 18, 2008, Crosby scored one goal and three assists to surpass benchmarks of 100 goals, 200 assists, and 300 points for his career. On the play in which Crosby scored, teammate Evgeni Malkin assisted to record his own 200th point. As a result, Crosby had a team trainer cut the puck in half so both players could commemorate the achievement. Minor injury troubles kept Crosby from five games early in the season as he was listed day-to-day, but he was, for the most part, able to bounce back from the previous injury-riddled season and stay healthy. He recorded 33 goals and 70 assists to finish third in league scoring, as Evgeni Malkin captured his first career Art Ross Trophy. Entering the 2009 playoffs as the defending Prince of Wales Trophy winners, the Penguins defeated the Philadelphia Flyers in the opening round before meeting the Washington Capitals for a highly publicized second-round matchup. The series was heavily followed as it pitted Ovechkin of the Capitals against both Crosby and Malkin, who together finished as the league's top three scorers that season. In the second game, Crosby and Ovechkin recorded matching three-goal efforts for their first career playoff hat tricks in a 4–3 Capitals victory. Despite being down 2–0 in the series, Crosby and the Penguins won the next three games and eventually defeated the Capitals in a seventh and deciding game, in which Crosby added another two goals. Following a sweep of the Carolina Hurricanes in the Eastern Conference Final, Crosby opted against recent NHL tradition and picked up the Prince of Wales Trophy, which he had left untouched the previous year. In explanation of the change of heart, Crosby said, "We didn't touch the trophy last year, and obviously we didn't have the result we wanted ... Although we haven't accomplished exactly what we want ... we can still enjoy it."

Crosby continues to be active in the community in Cole Harbour, Nova Scotia. He created the Sidney Crosby Foundation in 2009, an organization committed to providing support to charities benefiting children. In 2015, he launched an inaugural Hockey School in Cole Harbour. His "Little Penguins Program" has provided free equipment and lessons to more than ten thousand local youngsters in Pittsburgh.

Crosby's Penguins were defeated in the second round of the 2010 Stanley Cup playoffs, losing to the Montreal Canadiens in seven games. Crosby had 19 points in 13 games in the playoffs, though through seven games against the Canadiens, he had only one goal and four assists. Game 7 was also the last game to be played at Mellon Arena, the Penguins' home rink since the start of the franchise. On July 27, 2010, Crosby joined his mentor Mario Lemieux to be the first to skate on the new ice at the Consol Energy Center. The two skated for about five minutes before being joined on the ice by a group of young hockey fans all wearing Lemieux's 66 or Crosby's 87 jerseys.

Following the Penguins' second-round elimination in the 2010 playoffs, Crosby declined an invitation to join Canada midway through the 2010 IIHF World Championship in Germany. Crosby was selected to represent Canada at the 2014 Winter Olympics and was later named team captain. Canada won gold, with Crosby contributing one goal and two assists in six games. He scored his only goal in the final against Sweden, further establishing his reputation as "a player who rises up in big games". In 2015, Crosby captained Canada to its first World Championship title since 2007, with the team winning all 10 games and scoring 66 goals. Crosby, scoring four goals and seven assists in nine games, became the 26th member of the Triple Gold Club. He is the first member of the club to captain all three championship teams, and the first member to be a first overall NHL draft pick.

Following Crosby's Olympic gold medal victory with Canada in 2010, it was announced that his stick and glove were missing. It was initially suspected that they might have been stolen; Reebok Canada offered a reward of CAD$10,000 for their return, "no questions asked". On March 10, the items were found: Crosby's stick had been placed in a shipment bound for the International Ice Hockey Federation Hall of Fame in Saint Petersburg, Russia, (the shipment was intercepted in Toronto) and his glove was found in a hockey bag belonging to Olympic teammate and Boston Bruins' centre Patrice Bergeron, whose stall was beside Crosby's in the locker room.

On May 29, 2010, it was announced that Crosby would sign the richest endorsement contract in NHL history with Reebok, expected to pay Crosby $1.4 million per year for five to seven years. In 2015, he signed a six-year endorsement contract with Adidas. Crosby also has endorsement deals with Bell, Tim Hortons and Gatorade. Regarded as one of Canada's "legendary goal-scorers and storied leaders", Crosby was featured in Canada Post's NHL Great Canadian Forwards stamp collection, alongside Phil Esposito, Guy Lafleur, Darryl Sittler, Mark Messier and Steve Yzerman. In 2016, he won an Emmy Award for his role in There's No Place Like Home With Sidney Crosby.

In the 2010–11 season, Crosby had a 25-game point streak, which began November 5, 2010 against the Anaheim Ducks and ended December 28, 2010 against the New York Islanders. During this streak, he had 27 goals (including three hat-tricks) and 24 assists for 51 points. This streak was tied for 11th-longest point streak in NHL history, and he was named First Star of the Month in both November and December. On January 3, 2011, Crosby was selected as a 2011 All-Star, along with teammates Evgeni Malkin, Marc-André Fleury and Kris Letang. However, neither Crosby nor Malkin were available to play in the All-Star Game due to injuries, and rookie Jeff Skinner (along with Paul Stastny) were named as replacements. In consecutive games – the 2011 NHL Winter Classic on January 1, 2011, against the Washington Capitals and then January 5 against the Tampa Bay Lightning – Crosby suffered hits to his head from Dave Steckel and Victor Hedman respectively. After experiencing several concussion symptoms, Crosby did not return for the rest of the regular season, and he missed the 2011 playoffs. The Penguins were further crippled when Evgeni Malkin suffered a torn ACL and MCL, taking him out for the rest of the season and leaving the Penguins without their two highest-scoring players. Despite Crosby's injury and subsequent absence for the final 41 games of the season, he finished as the Penguins' leading scorer. His 66 points in 41 games were 16 points ahead of the second-highest team scorer, defenceman Kris Letang. In so doing, Crosby set an NHL record for fewest games played by an NHL team's points leader.

Crosby missed the first 20 games of the 2011–12 season due to the lingering effects of his concussion. He returned on November 21, 2011 in a game against the New York Islanders, scoring two goals and two assists in a 5–0 shutout for the Penguins. However, after playing another seven games – scoring a total of 12 points in 8 games – Crosby's concussion-like symptoms returned in December 2011, possibly following an elbow hit by David Krejčí in his eighth game of the season. Despite passing a successful ImPACT test, Crosby decided not to return on the ice until he felt perfectly fine, stating that he also must "listen to [his] body". Crosby returned to action on March 15, 2012, scoring an assist in a 5–2 win against the New York Rangers. Despite only playing 22 games, Crosby recorded 29 assists to go with 8 goals for 37 points, including his 600th career point. He later credited neurologists at UPMC and chiropractic neurologist Ted Carrick with helping him return to hockey.

Crosby's return in advance of the playoffs resulted in many experts predicting that the Penguins would win their second Stanley Cup title in four years, and though the Penguins were accordingly picked to oust the Philadelphia Flyers in their first round series, it was acknowledged that it would be a tough series for both teams. The Flyers shocked the Penguins by winning the first three consecutive games, the third of which saw the teams combine for 158 penalty minutes. After the 8–4 loss in Game 3, Crosby was widely criticized for his conduct during the game, and for his testy post-game interview. When asked about an incident where Flyer forward Jakub Voráček had dropped his glove and Crosby swatted it away with his stick before Voráček could pick it up, Crosby replied, saying, "I don't like any guy on their team there, so his glove was near me, went to pick it up, and I pushed it, so yeah, that's... [...] I don't like them. Because I don't like them. I don't like... I don't like any guy on their team." When the interviewer suggested that he could have skated away, Crosby replied, "Skate away? Yeah, well, I didn't that time." The Penguins went on to win the next two games, but ultimately lost the series in Game 6. Crosby would finish with three goals and five assists in the six games. On June 28, 2012, the Penguins announced that Crosby had agreed to a 12-year, $104.4 million contract extension set to keep Crosby in Pittsburgh through to the end of the 2024–25 NHL season.

The start of the 2012–13 was postponed until January 2013 due to the owners locking out the players as negotiations took place to solidify a new collective agreement for the players. During this time, Crosby was a regular attendee of meetings taking place between National Hockey League Players' Association (NHLPA) representatives and NHL owners. The lock-out began on September 15, 2012, and ended January 6, 2013, with the NHL regular season beginning on January 19. During the 119-day lock-out, Crosby was often questioned about his future plans should the lockout persist, and said on more than one occasion that he was entertaining contract offers from various teams in European leagues (where many NHL players went so that they could continue playing in a professional capacity while waiting for the lock-out to end or for the NHL season to be officially cancelled). Crosby continued to practice and participated with other NHL players who had not gone overseas in several exhibition games open to the public.

Crosby finished the 2014–15 season with the highest point-per-game average and a total of 84 points, trailing only John Tavares (86 points) and Art Ross winner Jamie Benn (87 points). On November 26, 2014, Crosby scored his 800th career point, becoming the sixth-fastest player in NHL history to reach that milestone. On January 4, 2015, in a game against Philadelphia, Crosby scored his 300th career NHL goal. Despite a strong start to the season, the injury-plagued Penguins entered the playoffs as the Eastern Conference's second wild card. Facing the New York Rangers, Crosby helped even the series with two goals in Game 2. Despite this, the Penguins were defeated in five games and was eliminated in the first round for the first time since the 2012 playoffs.

Crosby has a younger sister named Taylor who is a hockey goaltender. Like her brother, she went to high school at Shattuck-Saint Mary's in Faribault, Minnesota, to play with the school's hockey program. In 2014, Taylor joined the Northeastern Huskies women's ice hockey team as a freshman at Northeastern University in Boston. In 2015, she transferred to Minnesota's St. Cloud State University and played with the St. Cloud State Huskies women's ice hockey team through to graduation at the end of the 2017–18 school year.

Starting the 2015–16 season, the Penguins had gone through a major overhaul of their roster, adding a number of offensive players such as right winger Phil Kessel. Despite a line-up laced with some of the world's finest offensive talents, Crosby struggled to score points, as he and the team had for much of the Johnston era. By the time Johnston was fired on December 12, 2015, after posting a 15–10–3 record through 28 games, some media outlets began speculating that Crosby had aged out of his prime scoring years. On December 16, The Washington Post wrote, "Sidney Crosby has widely been regarded as the NHL's best player since he burst on the scene as a rookie in 2005 ... But Crosby just hasn't been himself this season, scoring just six goals in 29 games and sitting with a plus/minus of minus-seven. All players go through slumps, but it is clear that the Crosby we knew has been on the decline for some time." His slow start was capped off by not being selected as a starter for the 2016 NHL All-Star Game.

However, under new head coach Mike Sullivan, the 28-year-old turned his season around, outscoring all NHL players from December 12 through the end of the season. On February 2, Crosby scored three-straight goals for his first natural hat-trick in more than five years. Four days later, Crosby scored his 900th, 901st and 902nd career NHL points to fuel a 3–2 overtime comeback victory over the Florida Panthers. He tallied at least 1 point in 15 of Pittsburgh's 16 games in March, including six multi-point efforts, and was subsequently named the NHL's First Star of the Month. On April 2, Crosby recorded his 600th NHL assist as the Penguins clinched their berth in the 2016 playoffs. Six days later, he scored in overtime against Washington Capitals to secure home-ice advantage in the first round of the playoffs. Crosby finished the season with 36 goals and 85 points in 80 games, including a career-high nine game-winning goals, and was voted team MVP for the sixth time in his career. His two-way game also received league-wide praise, with Hockey Hall of Fame coach Scotty Bowman stating that Crosby would be a good candidate for the Frank J. Selke Trophy as the league's best defensive forward. Crosby's comeback also impressed Wayne Gretzky, who said, "He had a tough start, but the sign of an elite athlete is a guy that battles through it. He didn't point any fingers, he just battled through it, and I don't think there is any question the last 40 or so games, he made a case for the MVP. He was that good. He went to another level." On May 7, Crosby was named a finalist for the Hart Memorial Trophy. He finished as the first runner-up with 800 points and 11 first-place votes.

In 2016, Hockey Canada named Crosby captain for the 2016 World Cup of Hockey in Toronto. Crosby, who led the tournament in scoring with ten points, helped Team Canada win the championship, and was named the Most Valuable Player. He joined Bobby Orr and Wayne Gretzky as the only players to win the Conn Smythe, Hart Memorial Trophy and World Cup MVP. Team Canada head coach Mike Babcock described Crosby as a serial winner, saying, "He's that high-end competitor. He's a good leader because he tries to do it right all the time. He demands a lot out of himself. In doing so, he demands a lot out of his teammates."

Noted for his on-ice vision, passing ability, leadership, work ethic and complete overall game, Crosby is considered one of the greatest players of all time. Bobby Orr named Crosby among the five best players in the history of NHL. Wayne Gretzky said of Crosby, "He's proven over and over that he's the best player in the game today. And it seems like the more important the game, the more impact that he makes on a game." Gordie Howe was also impressed by Crosby, "I met him and I've seen him play. Unless you put two guys on him, he'll kill you in a game." In 2016, Mario Lemieux praised his protégé for his ability to play both sides of the puck: "I think he's more of a complete player. Defensively, I think he's improved a lot over the last couple of years." In an article for The Washington Post, other players, teammates and coaches highlighted his work ethic and strive for greatness as a major factor to Crosby's lasting success. "While his natural ability – powerful skating, pistol-quick hands, uncommon feel – made him a phenom, his creative, distinct capacity for work has enabled him to stay atop the NHL." Current Pittsburgh head coach Mike Sullivan described Crosby as "best 200-foot player in the game" and the "heartbeat" of the Penguins.

Crosby missed the first six games of the 2016–17 season after being diagnosed with a concussion just a few days before the season opener against the Washington Capitals. Upon his return, he scored 30 goals in his first 45 games, and on February 16, 2017, he registered an assist on a Chris Kunitz goal against the Winnipeg Jets to reach 1,000 NHL points, doing so in just his 757th game to become the 12th-fastest (and 11th-youngest) player to reach that milestone. He also participated in his first NHL All-Star Game since 2007, winning the shooting accuracy segment of the Skills Competition. He was named team MVP and finished the season as the runner up for the Art Ross Trophy with 44 goals and 89 points in 75 games. It marked the eighth time he finished a season in the top-three in NHL scoring, tying Mario Lemieux, Stan Mikita and Phil Esposito for the third-most instances in history behind only Wayne Gretzky (15 times) and Gordie Howe (12 times). With his 44 goals, Crosby captured the Rocket Richard Trophy for the second time in his career. Crosby was also named a finalist for the Hart Memorial Trophy and Ted Lindsay Award.

Entering the 2017 playoffs as the defending Stanley Cup champions, the Penguins defeated the Columbus Blue Jackets in five games before meeting the Washington Capitals in the second round. After winning the first two games on the road, Crosby sustained a concussion after suffering an injury from a slash and cross-check from Alexander Ovechkin and Matt Niskanen in Game 3. He missed Game 4 but returned to practice the next day and played in Game 5. The Penguins would eventually eliminate the Capitals in Game 7, with Crosby assisting on the series-winning goal. The Penguins then defeated the Ottawa Senators in a gruelling seven-game series to secure their second consecutive trip to the Stanley Cup Final. Crosby had the primary assist on the series-clinching goal, scored by Chris Kunitz in double overtime. Facing the Nashville Predators in the Finals, Pittsburgh jumped out to a two-game lead, despite being outplayed for long stretches in both games. The Predators responded by tying up the series, winning Game 3 and 4 at home. In Game 5, the Penguins' captain delivered a dominant performance, adding three assists in a 6–0 win to pass Lemieux for most Stanley Cup Final points (20) in franchise history. After defeating the Predators 2–0 in Game 6, the Penguins became the first team to repeat as Stanley Cup champions since the 1997–98 Detroit Red Wings, and the first to do so in the salary cap era. Crosby won his second consecutive Conn Smythe Trophy as the most valuable player of the playoffs, only the third player to do so after Bernie Parent (1974, 1975) and Mario Lemieux (1991, 1992). He finished second in scoring behind Evgeni Malkin with 27 points (8 goals and 19 assists) in 24 games.

On January 27, 2017, in a ceremony during the All-Star Weekend in Los Angeles, Crosby was named one of the 100 Greatest NHL Players in history. In that same year, Fox Sports ranked Crosby 15th on their "21 greatest athletes of the 21st century (so far)" list, and TSN named him the eighth-best NHL player of all-time. In a survey conducted by Sportsnet in June 2017, Crosby was voted by Canadians to be the greatest athlete of the 21st century. A poll conducted by the NHLPA in 2018 of more than 500 players resulted in Crosby being voted the "most difficult to play against, best role model, best team player, the player you'd want to win one game, and the player who would be a great coach upon retirement". In 2018, Crosby was chosen as Nova Scotia's "Best athlete ever" by the Nova Scotia Sport Hall of Fame. In 2019, an anonymous survey conducted by The Athletic showed that Crosby was regarded the best all-around NHL player by his peers.

In the 2017–18 season, Crosby appeared in all 82 of Pittsburgh's regular season games for the first time in his career, finishing with 29 goals and 60 assists for 89 points. On February 12, 2018, he scored his 400th NHL goal, becoming the 95th player to reach the milestone. On March 21, he recorded his 700th career NHL assist. The Penguins began their 2018 playoff campaign against the Philadelphia Flyers. In Game 1 of the Battle of Pennsylvania, Crosby recorded a natural hat-trick in a 7–0 win. On April 18, in Game 4, Crosby passed Mario Lemieux as the Penguins' all-time playoff points leader with 173. The Penguins ultimately defeated the Flyers in six games, with Crosby scoring 6 goals and 13 points. After the series, retired Hockey Hall of Fame centre Bryan Trottier said of Crosby, "Sid has a wonderful gift to maintain his composure and not get rattled. You like the emotion he shows, too. I think he fires his team up, and that's why he's wearing the 'C' [for captain]." The Penguins were eventually eliminated in Game 6 of the second round by the eventual Stanley Cup champion Washington Capitals, ending Penguins's bid for a three-peat. Crosby finished with 21 points (9 goals and 12 assists) in 12 games, pushing his career playoff total to 185, tied with Steve Yzerman for tenth-most all-time.

Rimouski Océanic retired jersey number 87 in Crosby's honor in 2019, and the QMJHL also retired the number for all of its teams.

On January 3, 2019, Crosby was selected to play in the NHL All-Star Game for the eighth time in his career. He scored four goals and four assists, helping the Metropolitan Division to victory; his efforts won him his first All-Star MVP award, making him the sixth in NHL history to have won that award after having won the Conn Smythe Trophy and Hart Memorial Trophy. During the 2018–19 season, Crosby passed Mario Lemieux to become the Penguins' all-time leader in games played (916), and moved into second place on the Pens' all-time scoring list with his 440th career goal in a 5–1 victory over the Montreal Canadiens on March 3, 2019. Two days later, he became the 48th player in NHL history to score at least 1,200 career points. On April 5, the Penguins clinched a playoff berth for the 13th consecutive season under Crosby's captaincy. He finished the season with 100 points (35 goals and 65 assists), the first time he has reached the 100-point mark since scoring 104 points in 2013–14. Crosby finished 4th in voting for the Selke Trophy and became a Hart Trophy finalist for the seventh time in his career. He was also elected team-MVP. In 2019, Crosby was selected to NHL All-Decade First Team.