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After back-to-back Stanley Cup championships for the Tampa Bay Lightning, coach Jon Cooper still couldn’t believe he was uttering these words:

“We’re going for three.”

The last time an NHL team won three straight Stanley Cups was from 1981-83, as part of the New York Islanders‘ run of four straight championships.

“‘We’re going for three.’ To say that out loud is kind of crazy,” Cooper told ESPN, before his team’s first-round playoff series against the Toronto Maple Leafs, currently tied 1-1. “You don’t get these chances often. They don’t come around. It’s like we’ve seen the top of the mountain. Let’s keep going for more.”

The chance to three-peat has only come around five times since the Islanders’ run, with the Edmonton Oilers and Pittsburgh Penguins going back-to-back twice and the Detroit Red Wings winning two in a row once. All failed to make it a hat trick.

If the Lightning win a third straight Cup, they cement themselves as a dynasty. If they fall short? Hockey Hall of Famer Mark Messier said that’s a special kind of pain.

“It was crushing. It was horrible. It was one of the worst experiences of our careers to be honest with you,” Messier said of the Oilers’ second-round loss to the Calgary Flames in 1986, which snapped their run of two straight Cups.

“When you win two in a row, it feels like the Cup belongs to you. To see someone else parade around the ice was not very pleasant.”

Messier had another back-to-back run with Edmonton, winning Cups in 1987 and 1988. Hockey Hall of Famer Larry Murphy also had two shots at a three-peat in the 1990s, with the Pittsburgh Penguins and the Detroit Red Wings. But it was that loss for the Penguins in 1993 — in the second round against the Islanders — that still haunts him.

“It was the most disappointing season in my career, without a doubt,” he said.

Aaron Ward was a defenseman for that Red Wings team when it won back-to-back Stanley Cups in 1997 and 1998, before losing in the second round in 1999 to their archrivals, the Colorado Avalanche.

“I don’t know if it’s any better to get eliminated in the Stanley Cup [Final], but to get eliminated in the second round … that’s pulling out your driver and not getting it past the novice tees,” he said.

As the Lightning push for the three-peat in the 2022 Stanley Cup playoffs, they’re discovering how hard the path gets during the third time around. Those who attempted the three-peat, but fell short, can relate.

‘We felt confident’

The Oilers might have had a three-peat, and limited the Islanders to just three Cups, had they won the 1983 Stanley Cup Final against New York. But they weren’t quite ready yet and were swept by the Isles for the latter’s Cup No. 4.

Instead, the Oilers prevented the Islanders from lifting a fifth straight Stanley Cup by beating them 4-1 in the 1984 Final, starting their own run of two straight championships — and getting them to start thinking dynasty.

“Our best chance was after we won in 1985,” said Messier, now a commentator with ESPN. “In 1986, we still had Wayne [Gretzky]. Our team was still positioned to win. We didn’t feel tired. We felt confident.”

Edmonton looked unbeatable in 1986. The Oilers had a .744 points percentage in the standings, best in the NHL. They averaged 5.33 goals scored per game — it was said at their peak in the 1980s, the Oilers would defeat their opponents before stepping on the ice through sheer offensive intimidation.

They demolished the Vancouver Canucks in three straight games in the first round of the playoffs. Then they met Calgary in the Battle of Alberta, and lost in a Game 7 that featured a monumental gaffe by defenseman Steve Smith, who banked a pass off goalie Grant Fuhr‘s leg to give the Flames a goal, the third-period lead and the win.

“We felt like we let one slip away in 1986. But we had a healthy respect for them. And a healthy dislike,” Messier said. “A lot of people would say that we got too complacent, but I don’t think we did. Calgary was a really great team that year. It came down to two really good teams and we didn’t play as well as we had to play.”

Messier still laments that missed opportunity.

“Did we have a good enough team to win? Yeah, we did. Did we win it? No. So it’s hard to say that we should have won it, because we didn’t,” he said.

The Oilers composed themselves and won two straight Stanley Cups again in 1987 and 1988. But in 1989, it was a transitional season for Edmonton. Paul Coffey had been traded to Pittsburgh during the 1987-88 season. Gretzky became the face of the Los Angeles Kings after The Trade in summer of 1988.

“It was a different team,” Messier noted of the 1989 Oilers.

The Lightning, for the most part, are not a different team this season. Messier expected big things from the Lightning in the playoffs.

“When I look at Tampa this year … you know, you can talk yourself into anything you want. If you’re physically or mentally tired, you can talk yourself into feeling great,” said Messier. “I’m pretty bullish on their team. They’ve solidified that bottom six a little bit better. With Andrei Vasilevskiy in net, they’re not going to be an easy out.”

‘When it comes too easy, bad habits creep in’

The core was solid for the 1990-91 Pittsburgh Penguins, when they won the franchise’s first Stanley Cup: Mario Lemieux, Jaromir Jagr, Ron Francis, Mark Recchi, Joe Mullen, Coffey and Murphy are all Hall of Famers.

The core was still solid for 1991-92 Stanley Cup champion Penguins, although Recchi had been traded for defenseman Kjell Samuelsson, forward Rick Tocchet and goalie Ken Wregget; Coffey had been moved to the Kings; and Scotty Bowman took over for Bob Johnson behind the bench.

In 1992-93, many outside the team were expecting a Penguins dynasty, although they were trying to tamper those expectations.

“It was similar to the previous season. There wasn’t a lot of talk about the big picture. It was just about trying to win that year,” said Murphy. “There was a sense that Mario’s here, so our chances are even better. And then it turned out that wasn’t the case.”

Lemieux missed a quarter of the season due to Hodgkin’s lymphoma, but returned to have the Penguins rolling into the playoffs. They beat the New Jersey Devils, 4-1, in the first round. But then the Islanders shocked them in Game 7, on David Volek‘s series-winning goal at 5:16 of overtime.

“Things were moving along nicely. But then we run into the Islanders, and it’s all for naught,” recalled Murphy. “It was just a sense of huge disappointment. The opportunity doesn’t present itself every season.”

His theory behind the Penguins falling short of the three-peat?

“What hurt us is that it came too easy at the end of the season. If we had struggled going into the playoffs, I think we would have fared better,” he said. “And when it comes too easy, then bad habits creep in, and that’s what happened that year.”

Murphy would get another chance at a three-peat with the Red Wings after they won in 1997 and 1998.

“Right place at the right time,” he joked.

The Red Wings swept the Flyers for the 1997 Stanley Cup. But the dynamic changed dramatically in 1998, according to Murphy. After the Cup celebration, a limo containing defensemen Vladimir Konstantinov and Slava Fetisov hit a tree. Konstantinov spent several weeks in a coma. His hockey career ended due to paralysis suffered in the accident.

Murphy said having Konstantinov around the team, including in their Stanley Cup celebration in 1998, was an inspiration to win back-to-back Cups.

“It definitely gave us motivation. To win it for Vladdy,” he said.

“Winning that first one, there’s that drive to win it for the first time. The second time, it’s a continuation. It’s a different sort of motivation. The third is like, ‘We know what it’s like to win the Cup. Let’s do it again.'”

But the run would stop at two Cups for the Red Wings.

‘Why wouldn’t we be able to do it again?’

Aaron Ward remembers the dynasty talk for those Red Wings.

“That was what our media was talking about. The Detroit News and Detroit Free Press, at the time, were always talking about whether it was going to be a dynasty. And there was a plan in place to definitely win a third and maybe even challenge for a fourth,” he said.

The fans loved it. Coach Scotty Bowman did not.

“It would frustrate Scotty. He wants to control the message. He doesn’t want anyone on his team thinking about any f—ing dynasty,” said Ward.

The former NHL defenseman knows what the Lightning are going through this season. Ward noted that Tampa didn’t play its sharpest hockey in the regular season, despite amassing 108 points.

He watched as Tampa Bay added Brandon Hagel and Nick Paul at the trade deadline — and remembered the 1998-99 Red Wings.

“From what I remember of the 1998-99 season was this feeling of just getting through to the trade deadline. Get yourself well-positioned. Inevitably, the organization was going to go out and get key pieces. They’ve done it in previous years. Remember, there was no salary cap [at that time],” he said.

At the trade deadline in 1999, the Red Wings acquired defenseman Chris Chelios from the Chicago Blackhawks, forward Wendel Clark from the Tampa Bay Lightning and Ulf Samuelsson from the New York Rangers.

“So it played out exactly as we thought. [GM] Kenny [Holland] would make major acquisitions. When those three guys came in, I was like ‘Chalk it up, we’ve got another Stanley Cup here,'” said Ward. “When you’ve won it two years in a row, the feeling was that you had to maintain enough focus to get to the playoffs and then in the playoffs, that’s where the war begins. We’ve proven ourselves capable in two previous years, why wouldn’t be able to do it again?”

The Red Wings finished first in the Central Division with 93 points, which was the third most in the Western Conference. They swept the Mighty Ducks of Anaheim in the first round, outscoring them 17-7. But then they met the Colorado Avalanche for the next chapter of their storied feud — the Avs eliminated the Wings en route to the Stanley Cup in 1996, and the Wings did the same to the Avs in 1997.

Detroit won the first two games in Denver. The Avalanche roared back to win four straight and eliminate the Red Wings in six games.

“The weird part from that one was … we weren’t complacent, but we didn’t have an answer,” said Ward. “Because we acquired those guys and we had the depth that we had, we felt pretty confident. Something about that series just didn’t work for us. Colorado seemed to have an answer, in the same way we had the answer in 1996-97. It all went across the net. They were in control. We just couldn’t do it.”

The players were left wondering why what used to work to championship perfection no longer did. “We were still playing left wing lock. We were still playing the Scotty Bowman system,” said Ward. “Maybe that system had expired. Maybe they figured something out. But we were having trouble defensively against the Colorado Avalanche.”

Ward said to not complete the three-peat was a “massive frustration” for the Red Wings.

“In the two previous years, you’ve proven to yourself that you know what it takes. It’s in your back pocket. It’s almost like a cheat sheet that you can consult. You’ve encountered every possible type of adversity that can be thrown at you,” he said. “The immediate reaction was a high level of frustration.”

Will the Tampa Bay Lightning feel the same thing before the end of June?

‘Don’t squander an opportunity’

The Lightning’s Stanley Cup wins in 2020 and 2021 came in truncated seasons with untraditional postseason formats. While no one is saying there should be an asterisk next to either of them, the Lightning are trying to win a third straight chalice in an 82-game season with a compressed schedule.

While other three-peaters have played more games, none have had to win during the unique tensions of playing through a global pandemic, which the Lightning have.

“The situation with COVID, the disruptions of the seasons and the shorter seasons, you’re dealing with something that’s never been dealt with before. They’re a deep team. Last year, they were fortunate with the salary cap situation,” Murphy said, in reference to the Lightning getting star Nikita Kucherov back for the playoffs after spending the entire season on long-term injured reserve. “It’s an experienced team that, when you watch them play, they just know how to do it.”

Messier has been impressed with all the teams that approached dynasty status in the salary cap era. Along with the Lightning, the Penguins won back-to-back Cups in 2016 and 2017. The Chicago Blackhawks didn’t win back-to-back Cups, but they did win three Stanley Cups in six seasons (2010, 2013, 2015).

But due to the salary cap, the 2010 Blackhawks had to jettison a good portion of their supporting cast.

“It’s a lot harder now. You’ve really gotta tip your cap to Pittsburgh and Chicago for winning three and Tampa Bay winning two now,” said Messier. “It’s hard to keep a core together. And then you have to support them, because a core alone won’t get a Stanley Cup done.”

It also takes patience. The Lightning lost in the Stanley Cup Final in 2015, and the conference finals in 2016 and 2018. Then came the critical moment: Getting swept by the Columbus Blue Jackets in the first round of the playoffs in 2019, after a 128-point regular season.

Then came the back-to-back Cups.

“After 2019, I was a little skeptical, I’ll tell you that. But we kept the band together. We kept the faith,” Cooper said. “To be in this position, it takes a lot of good players. It takes a staff. It takes the right management positions. It takes an owner. They put us in a position where we can make the playoffs every year. But you’re not going to win every year, we understand that. We get a chance to take a swing for the fence, we’re going to do that.”

It’s a mighty big swing to try to win three straight Stanley Cups. Others have tried to do it since the Islanders’ dynasty in the early 1980s, and all have failed.

What would Larry Murphy, who nearly pulled the three-peat with two franchises, say to the Lightning today?

“I would say to them as I would say to any other team in any other playoff: Don’t squander an opportunity. You want to feel like at the end of it that you didn’t leave anything on the table,” he said. “But everything is easier said than done. They might want it just as much as the last two seasons, but for whatever reason, it won’t happen for them.”