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The Edmonton Oilers’ greatest feat ever was assuredly their fifth Stanley Cup in 1990. To win a Cup not only without Wayne Gretzky, but Grant Fuhr and the previously-departed Paul Coffey was significant. Add on all the adversity the Oilers had to tackle during the 1989–90 season, and it was a most impressive accomplishment all around.

The question automatically then becomes, can you do it again? The 1984 and 1987 teams both followed up Cup championships with a repeat win. And entering 1990–91, a lot of the pieces remained from the previous season, including Mark Messier as captain. Things looked perfect for a third back-to-back in the franchise’s young history.

How similar were the 1989–90 and 1990–91 rosters

To a point, rather similar, but with one major exception. Another franchise great, Jari Kurri, declined to accept a new contract from the Oilers prior to the 1990–91 season. He would play in Italy for a year before coming back to the NHL, his rights having been traded from Edmonton to the Los Angeles Kings, by way of the Philadelphia Flyers.

Apart from Kurri, the other core pieces remained in place in 1990–91. The other departures were more role players, headlined by another five-time Cup champ in Randy Gregg. Yes, the same Randy Gregg behind the Edmonton Riverhawks baseball franchise.

Another successful regular season

The Oilers actually began this season worse than they began 1989–90, with a wretched 2–11–2 start. Complicating matters was they did not have Fuhr for most of the season, and Messier would miss nearly 30 games due to injury. The Oilers wouldn’t win a road game until November 24, at Maple Leaf Gardens in Toronto.

Like the season before, though, the team would rally in the face of adversity. Between November 14 and January 22, the Oilers would go 27–9–1, including 11–3–0 in the month of December alone. That stretch cancelled out the rough start and then some, putting them right back into the upper half of the standings. Bill Ranford built on his Conn Smythe-winning 1990 playoffs with a solid 1990–91 campaign, and players who had stepped up the year before continued to do so.

The Oilers finished 37–37–6, which in the current day and age wouldn’t be anywhere close to a playoff spot. But in 1991, as we’ll note a little later on here, there were several teams who ended with a worse record than .500. By 1991 standards, this finish was good for third place in the Smythe Division.

The Modano-led North Stars pull off the surprise

The 1991 Stanley Cup Playoffs started off surprisingly similar to the years of past for Edmonton. Series wins over the Kings, and the Calgary Flames , the last playoff Battle of Alberta we’d see for 31 years. The 1991 edition is best remembered for the two teams trading Overtime winners on their opponents’ ice. Theo Fleury did it in Edmonton in Game 6, before his knee-slide celebration down the ice. Fortunately, the Oilers still had Esa Tikkanen around to respond in Overtime in Game 7.

Over in the Wales Conference, the Mario Lemieux- and Jaromir Jagr-led Pittsburgh Penguins were finally breaking through. After a tough seven-game series in the first round with New Jersey, the Pens won their next series in five games. Following that dispatching of the Washington Capitals, they knocked out the Bruins in six. Lemieux, in his seventh NHL season, had already risen to a status of being one of the best NHL talents not named Gretzky. Coffey played there now. Pittsburgh was looking to be perhaps the next great dynasty. They would be able to take on the Oilers, if Edmonton could just get past one more round.

The Minnesota North Stars finished 27–39–14 in the 1990–91 season, making the playoffs as a seventh seed. They finished just three points ahead of eighth-place Vancouver, who represented the playoff cut line. Even though this was a team that featured a young Mike Modano, there wasn’t much of a reason to believe they would go far. The Oilers had faced them in the Conference Final once before, in 1984. It ended in a sweep.

But even in 1991, all you had to do was make the playoffs, and magic could happen. The North Stars lost their first home game of that run 6–5 to the Chicago Blackhawks. They would not lose another home game until the Stanley Cup Final. On top of that, they were able to steal defensive-style wins on the road, with Jon Casey providing solid goaltending. In short, they became the hottest team in the NHL in April and early-May 1991.

The North Stars remained hot in the Conference Final

Minnesota stayed true to that script against the Oilers. They came away with a tight 3–1 win in Edmonton to open the series up. Well, okay, Edmonton had spotted the Jets a road Game one victory the year before. They can come back from that.

Game 2, the Oilers responded emphatically with a 7–2 win, the last time they’d register a playoff seven-spot until 2017. See, there’s the glory-days Oilers’ we’ve become accustomed to covering in these Lookbacks. All should be fine.

This was where the ride came crashing to a halt. The North Stars still refused to let any opponents win a game at the old Met Center. Neither Game three nor Game 4 was particularly close, with 7–3 and 5–1 scores respectively. The ability to steal a road game was no longer there for Edmonton.

Game 5 would be close, too. But Minnesota repeated what they did in Game 1: a tight, 3–2 victory on Coliseum ice. We would not get the Oilers-Penguins matchup we had all hoped for in the Stanley Cup Final. There would be no third repeat championship for the Oilers.

1991–92: No Messier in the room now

Still plagued with the financial troubles they had been dealing with all this time, the Oilers would have to make more moves in the 1991 offseason. One such move would be to let Adam Graves sign an offer sheet with the New York Rangers. Another would be allowing coach John Muckler to depart for Buffalo.

The major trades were still to come, however. First of all, after significant missed time the past two seasons, Fuhr would be moved, along with Glenn Anderson, to the Maple Leafs in exchange for a package headlined by Vincent Damphousse. Just before the regular season, however, would land a move even more seismic.

Messier, frustrated by all the cost-cutting moves in the organization, had requested a trade. On October 4, 1991, that request was fulfilled, as he was shipped off to the New York Rangers. One of the pieces in return, besides Bernie Nicholls? A young kid who had just taken part in a Las Vegas outdoor game against the Kings, named Louie DeBrusk.

With Messier gone, Kevin Lowe would not only be the last future Hall of Famer left on the team. But he would also become the captain, with dynasty links Tikkanen, and Craig MacTavish, as alternates. It would be their job to return the team to the promised land once more.

Marginal improvement in the standings, and a 13th consecutive playoff berth

Once again, slow starts were the name of the game, as the Oilers commenced by going 1-5–1 through the first seven contests. They would recover for the rest of October, getting back to 5–6–2 by Halloween. November proved to be the most cursed month on the calendar for Edmonton, and January wouldn’t fare much better. But they would dominate the December, February, and March portions of the schedule to balance that out.

Ranford was once again a huge key to their regularseason success, backstopping 27 of the team’s 36 wins on the year. Despite one fewer win, the Oilers also had three fewer losses on their final record. A 36–34–10 finish put them two standings points higher than the previous season, and once again netted them third place in the Smythe.

One last deep playoff run ends the same as the playoff run before

Somehow, the Oilers still had it in them to make a point of knocking out Gretzky and the Kings in the playoffs. They would do that in the first round this time, a plot line that would be followed heavily in the 2020s. Like this most recent postseason, Edmonton won it in six games.

While Paula Abdul was rocking at Northlands Coliseum, the Oilers were opening up a second-round series against the Vancouver Canucks. The Canucks went nowhere in 1991, but had gotten better for 1992. Their time was not yet, however, as the Oilers dispatched them in six games like was done to .LA.

This set up a Conference Final with the Mike Keenan-led Chicago Blackhawks. The Oilers had eliminated these same ‘Hawks in 1990 en route to a Cup. Maybe this was an omen of good things to come.

Not to be, however. To the tune of 21–8, the Oilers were badly outscored as Chicago emphatically swept Edmonton. Once again, an Oilers-Penguins Cup Final would not become a reality. What offered one last glimmer of hope for the Oilers dynasty, instead signalled the likely end of an era.

The Oilers could make do without one or two of their key pieces. Heck, they could win a Cup without the face of the NHL. But by this time, too many franchise greats were departed, and the Oilers could no longer dominate like they used to. The dynasty was set to end.

From the writer’s desk, warmest regards and appreciation

The “Franchise History Lookbacks” series has been a fascinating one to write over the past month and a half. This observer certainly hopes it has been well-liked, and that it can continue again when the next lull comes around.

For now, though, a new season is dawning. Training camp is underway, and the Oilers’ first official preseason games are tomorrow against Calgary. Do enjoy hockey’s return, and hopefully we shall reconnect for this series in the not too distant future.

This article first appeared on The Oil Rig and was syndicated with permission.

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