If winning one Stanley Cup is the equivalent of hitting the Powerball, then winning twice in a row is like hitting the Powerball after getting struck by lightning.
And three times in a row?
The commonly called "hardest trophy in sports to win"?
There’s good reason why no team has lifted Lord Stanley’s chalice three consecutive years since the Islanders' four-term dynasty of 1980-83 with Mike Bossy, Denis Potvin and Bryan Trottier, among others. Since then, four more teams have set that stage and fallen short, including the David Volek-toppled Penguins of 1993.
These current Penguins are hoping to not become the fifth:

But it will be difficult in so many ways.
For one, this era of the NHL has seen unprecedented parity, in part because of a salary cap that's prevented anyone from spending excessively. Not many realized it at the time, but the 1991 and 1992 Penguins led the league in payroll both seasons. And until June 11 in Nashville, no team had even won back-to-back Cups since the 1997 and 1998 Red Wings, a half-decade before the cap.
For another, there is the toll that this game can take on one’s body and mind after having played more than 200 games the previous 30 months. Since their 2015-16 season opener Oct. 8, 2015, in Dallas, and running right through Tuesday night's 4-3 loss to the Rangers, they've now logged 193 regular-season games and 49 playoff games -- 242 total -- in the span of 790 days.
That's one game every 3.26 days including the offseasons!
“Three in a row is quite the challenge," as Sidney Crosby told me. "But we’ve put ourselves in the best position to have that opportunity.”
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Greatness had been predicted, if not expected, of Crosby by the time he was 12, still shooting pucks into his mother’s dryer in Nova Scotia, scarfing down Timbits on his way to early morning practices.
Much has changed for Crosby since then, notably the donut holes.
With three Cups and counting, not to mention two Olympic gold medals and a World Cup, the now-30-year-old has already vaulted into a group of the game’s all-time greats, a rank further legitimized by this past summer's latest parade down the Boulevard of the Allies. But, even as he is as knowledgeable about hockey and its history as any modern player, even as he still has so much hockey left, he prefers to live in the moment.
That legacy stuff?
“Really, I don’t think about it at all,” the captain was telling me. “If anything, you just want to be a good professional and be accountable to your teammates and, at the end of the day, you want to win and be a part of winning teams and things like that. I just think when you look back at things, you just want to be remembered as a good teammate and someone who showed up and was a true professional. If you can say that at the end of your career, that’s probably the biggest thing.”
Regardless, this season, the best player of this generation is chasing ghosts and gods. Crosby has an opportunity to do what Gordie Howe, Bobby Orr, Wayne Gretzky and Mario Lemieux — the Mount Rushmore of Hockey to most— could not. All but Orr won two Cups in a row, but none stretched it to three.
Howe’s Red Wings won in 1954 and 1955 but were rubbed out in the 1956 Final, 4-1, by Rocket Richard's Canadiens. Orr's Bruins won in 1970 and 1972 and never had a crack. Gretzky’s Oilers dethroned those Islanders in 1984 and 1985 but were stunted in the second round in 1986 by the Flames and a devastating own goal. And Lemieux’s Penguins in 1993 ... you know.
A three-peat and eclipsing all of the aforementioned — including Lemieux, his employer, former landlord and forever friend — “would be unbelievable,” Crosby confessed. But his stance is that he can only control what he can control now, not events that are six months away.
“Three in a row is quite the challenge, but we’ve put ourselves in the best position to have that opportunity,” he said. “We’ll see what happens with the way the division is and things like that, that’s on our mind now. We have to make sure we think about this and can’t think too far ahead.”
His pragmatism stems from a sluggish start to the season that saw the Penguins go an un-champion-like 11-10-3. Crosby had just six goals and 11 assists in the first 23 games of the season, good for most, but hardly fitting his career 1.31 points per game average and title as the best player of his generation. He has since followed that up with six goals and six assists in the past five games. Not coincidentally, the Penguins were able to piece together a four-game win streak, their longest of the season.
There is a correlation, however, between Crosby’s slow start and that of his team. Spoiler alert: It’s not a lack of talent. And, no, it’s not the penalty-kill or lack of secondary scoring.
Take those 242 total games over the past two-plus seasons, then throw in the first eight back-to-back sets — out of a league-high 19 on the schedule — and that only begins to paint the picture of this third-chapter grind that began anew just three months and 23 days after showering off all that champagne and flying out of Music City.
All concerned with the Penguins have grasped that probably since that charter took off. They knew this journey would have to be different. With a few different players. With different regimens. With a different mindset.
An hour-long practice Tuesday morning at PPG was the exception, not the norm this season. Because of the schedule, Mike Sullivan said his practices this season have been more about recovery than teaching actual Xs and Os on a rink-side whiteboard. The teaching has been almost secondary as the Penguins have been, figuratively, doing nothing but “just play,” to use a Sully-ism. And usually on the road, where 14 of the first 21 games were.
“You’re in a hallway,” Kris Letang said, referring to doing calisthenics or riding a stationary bike on the road. “Yes, you have a couple weights but it’s not like having all the tools that you have here. And, obviously, right after games you have back-to-backs, you don’t have time to train. You have to get to the next city.”
Crosby is a rink rat from birth, a creature of habit whose pregame routine includes working on his stickhandling by toe-dragging a puck around the golden arch of the McDonald’s logo painted on the ice at PPG and countless other quirks. Unless injured, he loathes leaving the ice.
But in a concession to age and circumstances, Crosby says he has scaled back, at least a little.
“It’s more about maintenance as you get older,” he said. “You play games, you go through different things injury-wise, things like that, you are more apt to try to rest and get back to feeling 100 percent than you are to really go and push yourself in the gym and things like that. There’s a time and a place for it, but with a short summer, you only have so much time to do so many things.”
The morning skates, a staple in the NHL for the better part of the last half-century, have increasingly become optional, and Sullivan's no exception. The choice to skate on gameday mornings depends simply on how he feels and if there is any benefit to be gained. Crosby, Phil Kessel and Patric Hornqvist routinely bypass them, preserving themselves for faceoff.
For Crosby, the challenge of the three-peat is more physical than anything. It’s not what happens October through December — or, really, October through March — that will define him or the Penguins.
“I think the last couple years, with the amount of games we’ve played, you try to get the rest during the season while you can,” Crosby said. “Obviously in the summer you can push yourself a little bit more and kind of gain things that way, but as far as in-season, yeah, I think it’s just about managing your body and making sure that you are as rested as you can be when you go out there and play.”
The name Andy O’Brien is obscure to most everyone. Even the most diehard fan has probably never heard of the Penguins’ director of sports science, but at least one person considers him to be Pittsburgh’s secret weapon.
“I think, truthfully, that’s where the Penguins have an advantage. They’ve got one of the best in the business at what he does,” said Gary Roberts. “I think, looking from the outside, I think he’s had a big impact on their ability to win not just one Cup but two.”
Roberts would know. The former Penguins left winger now serves as the sports performance director at the Lemieux Sports Complex. He was an early convert to the importance of training after a neck injury threatened to end his career at age 30, and he educated himself on all things training related and was able to play into his late 30s.
To hear Roberts, the Penguins’ emphasis on recovery has been, and will continue to be, crucial to their sustained excellence.
“It’s all about recovery,” Roberts said. “The moment the game’s over, what do you do to give yourself the best possible chance to recover? It’s not like football where you’re playing one a week. Hockey, you’re playing four games a week and at the level they play, it’s all about recovery.”
Roberts said recovery doesn’t mean rest, at least not alone. It encompasses nutrition, lifestyle choices, water intake, and sleep, according to Roberts. All those factors become even more vital when you’ve played as many games as the Penguins have and as many on the road.
As a player, the only thing that took Roberts off the ice was injury. He was the ultimate competitor, racking up 2,560 penalty minutes in 1,224 games.
While teams in other sports will often sit out a player to preserve him for the postseason, Roberts says that just isn’t the hockey culture.
“That," he said, "is why it’s the greatest game in the world.”
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With a resume that includes a record 14 Cups as either a coach or executive, and as one of just two men in modern NHL history to win it not three but four straight times, Scotty Bowman is uniquely qualified to discuss dynasties.
But not even the most accomplished coach in league history could win the Cup three years in a row every time he had the chance. Bowman guided the Canadiens of the late 1970s, arguably the best team of all time, to four in a row, but failed in two later attempts to win three straight. Two years after he took over for the late Bob Johnson in Pittsburgh, Bowman was behind the bench in 1993, losing despite the most formidable roster the franchise has ever seen. Six years later, after leading Detroit to consecutive titles, Bowman’s Red Wings blew a 2-0 series lead, losing to bitter rival Colorado in the second round.
“No two years are even close to being the same,” Bowman told me. “I think once you’ve done it, you get a chance to do something a lot of teams don’t do. Two is not easy and, of course, three is more difficult. We know that.”
Of course, when Bowman’s Canadiens and Red Wings — or Glen Sather’s Oilers and Al Arbour’s Islanders — were repeating as champions, they did so without a cap. And they did so at a time when free agents didn’t defect until their early 30s.
Bowman knows how that works, too. Working as the senior advisor to his son, Chicago general manager Stan Bowman, the 84-year-old Bowman has seen the Blackhawks win three Cups in a six-year span between 2010-15. But the Blackhawks, who join the Penguins with the most Cups in the new century, have never won two in a row, let alone three.
The NHL is, first and foremost, a business. Many factors conspire against teams winning repeatedly, but always remember to follow the money.
“It’s a lot different now,” Bowman said. “You’d like to have the same roster as you had the year before and playoffs, but obviously changes have to be made now, more so than before. Before, a couple of changes, adding a couple of players to the ones you have, was always a good asset. Nowadays, you have to have replacement players. You can’t keep everybody, especially on a team that’s successful and you have contracts that are expiring. You have to fit everybody under the salary cap.”
This past summer, the Penguins saw the free agent departures of Chris Kunitz, Nick Bonino, Matt Cullen, Trevor Daley and Ron Hainsey, all valuable contributors. And still the Penguins are currently right up against the cap with only $762,942 to spare, according to Spotrac.com.
“Keeping your team intact is not easy,” Bowman said. “Probably the most important thing is who you can bring in to replace the guy.”
The Penguins signed Matt Hunwick in free agency, traded for Ryan Reaves and for Riley Sheahan and are looking to get continued production from a bunch of youngsters — like Jake Guentzel and Bryan Rust — still on entry-level contracts. Under Jim Rutherford, they seem to have mastered the prototype for a successful organization in today’s NHL: Identify a group of core players — Crosby, Letang, Kessel and Evgeni Malkin — and build around them with younger, cheaper complementary pieces.
“It’s pretty impressive,” Bowman said of the Penguins. “They had players up from their minor-league team and some of them had really good rookie seasons and some had a good playoff. That’s the trick. It’s not easy when you have big stars on your team that you’re paying heavy contracts to, and they deserve it. It’s hard to find players that can help those guys because you’re not going to be able to take on expensive players. But sometimes you find players because you give them a chance and you give them an opportunity.”
An opportunity is exactly what Bowman believes the Penguins should have again this spring. Nothing more, nothing less. They certainly have the experience, the stars, the supporting cast — for the most part — and the starting goalie to do it.
But there are so many X-factors, so many variables, he said, it’s nearly impossible to predict in the first week of December.
“I think the challenge is to not to get too high, not get too low during the season. Once you get cranked up, and if you get in the playoffs, then everything changes again. Then you’ve won the year before. The big thing is the regular season.”
But, as Bowman is well aware, some things are simply out of your control.
“Sometimes teams are better than you or you get into a certain situation with your goaltending or the health of your team; that’s always a big factor. When you’re in the playoffs, it’s how healthy can you stay because it is a grind trying to play 20-whatever, 25 games maybe, to win the Cup. It’s not easy.”
There is no rest. The challenge of the three-peat is the grind, Bowman says.
"You have to go for it."
