Five games remain in the Red Wings’ quest, not only to make the 2016 Stanley Cup Playoffs but to extend what’s become known in Detroit as “the streak”. We all love to debate streaks in sports, be it for individuals and teams alike, but the merits of this particular one in Detroit are now being frequently debated and have been for the past three seasons, with playoffs anything but a certainty.

A playoff berth this year, regardless of how long it extends their season — and three of the past four seasons, they’ve made first-round exits (the franchise is 15-23 in their past 38 playoff games, dating back to Spring 2011) — matters a lot more to some Red Wings fans than it does others.

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Well, this weekend marks the 26-year anniversary of the final regular season game of the last Red Wings to actually miss the playoffs, the 1989-90 Red Wings. I thought it’d be interesting to flashback and look at why this team missed, despite having a superstar in his prime, plenty of complimentary talent, and a head coach who’d win the Stanley Cup a mere three years later.

Admittedly, there was a bit of a hangover coming into the 1989-90 season for the Red Wings, following a surprising upset in the first round of the playoffs. The Wings had won the Norris Division a second straight season, with 80 points in 80 games, but had crash-landed at the end of the regular season, losing six of eight games. They held off the North Stars by two points for the division crown, but it was nowhere near the 90 point season the Wings had the year before when they cruised through the first two rounds of the playoffs, and put a mild scare into Edmonton in the Western Conference Finals, despite missing Steve Yzerman the first two games of the series, and of course the infamous “Goose Looneys” bar night involving several players the night before (and morning of) Game 5 in Edmonton.

The Red Wings ended up losing in six games to a Chicago team that finished with 66 points, the worst record by far of the 16 teams to make the playoffs. The Blackhawks still got the 6th overall pick (Adam Bennett), while the Red Wings picked 11th (Mike Sillinger). The series ended with a humiliating 7-1 defeat at Chicago Stadium in Game 6, in which the Hawks scored four power-play goals past the combo of Greg Stefan and Glen Hanlon, each of whom had played so well at different times in the previous two springs.

The Red Wings moved some bodies in, and some bodies out prior to the 1989-90 season, but what stands out is the exceptional 1989 NHL Entry Draft they put together. Following the Sillinger pick at #11, they took defenceman Bob Boughner at 32nd overall in the 2nd round, Nick Lidstrom at 53rd in the 3rd, and Sergei Fedorov at 74th in the 4th. Follow that up in later rounds with Dallas Drake and Vladimir Konstantinov, and it simply is one of the most stunningly talented drafts any NHL team has ever put together. Two 1st-ballot Hockey Hall of Famers, a player who might have pushed to be in the Hall in Konstantinov before the tragic limo accident, and very steady and much-travelled NHLers in Sillinger, Boughner, and Drake.

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Unfortunately, this draft provided virtually no help for an aging core in Detroit during the upcoming 89-90 season. Sillinger was returned to Regina for more WHL hockey, and wouldn’t play consistently with the Wings until he was 21, Boughner wouldn’t become an NHLer until he was 24, then part of the Sabres’ organization and Fedorov would stay one more season before defecting in the summer of 1990, while Lidstrom stayed in Sweden until 91-92, when he and Konstantinov would both join the Wings as rookies, and instantly play in their top four D.

Given there’d be no contributions coming for the Red Wings from the Draft, this made what happened two days prior to the Draft, more disastrous, at least for the upcoming season, than anyone could have imagined. That said, when I first heard of this trade, I knew I hated it, but it took several more years of watching Adam Oates pile up the points in St. Louis and Boston to know how much I hated it.

Looking for a shakeup, GM Jim Devellano and head coach Jacques Demers also determined to get OLDER and bringing in players who could “lead” despite being so obviously on the downward slopes of their productivity was the way to go. Thus, Adam Oates and Paul MacLean were traded for Bernie Federko and Tony McKegney. Beyond awful.

The 26-year old Oates, coming off a 78-point season (best of his career, and third-straight very productive campaign), and 31-year old Paul MacLean, who played on the Red Wings first line with Steve Yzerman and Gerard Gallant most nights the prior year, were gone. MacLean had just arrived in Detroit the prior offseason when Jimmy Devellano gave up only Brent Ashton back. MacLean had averaged 35.4 goals/season in his seven years in Winnipeg, not easy to do even in the Smythe Division going against Edmonton and Calgary sixteen times a year. In 88-89, he easily put up 36 goals and 35 assists riding shotgun on Yzerman’s wing.

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Demers is often blamed for putting the hard sell on Devellano to do this, but Devellano could easily have said no. Federko was 33 and was practically out of gas. He never clicked in Detroit and after a 17-goal season, promptly retired at age 34. McKegney had scored 65 goals combined in the previous two Blues’ seasons but also found his Detroit stop frustrating. He couldn’t get anything going and was miserable. After 14 games, he was shipped to Quebec, for 29-year old forward Greg Adams, and 33-year old defenceman Robert Picard. Little gained by either team in that transaction. Picard was a former #1 D-man, but that was ages ago, and he retired also when his lone Wings season ended.

Another offseason move that caught attention was that of the signing of Maple Leafs legend Borje Salming. Perhaps wanting a change of scenery, and more than likely, beyond sick and tired of the seeing all the shenanigans play out of the Harold Ballard Era, Salming headed west on the 401 to play home games at Joe Louis Arena. It was quite odd, and even those close to Salming weren’t quite sure how it all played out. If he wanted one last shot at playing in a Stanley Cup Final, there were other destinations besides Detroit in 1989 to consider. Either way, he fit in and though we now regard plus-minus as an antiquated statistic, and properly so, it does tell something of Salming’s consistency that he led the entire club with a +20, on a team that gave up more even-strength goals than it scored (actually by only one, 230 for to 231 against)

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So in October 1989, the Red Wings start poorly. Outscored 20-10 in their first THREE games, all out West against at Calgary/Vancouver/Winnipeg. That’s a tough stretch to start the year with, admittedly, but the goals against issue was a bit of an omen. The Wings then win four of their next five, stabilizing the early concerns.

But on November 2nd, with a record of 4-6-3 and following a 5-5 tie at home against the Flyers, the Red Wings pull the trigger on a trade meant to give them a 2nd superstar centre to slot in behind Steve Yzerman, and also move out a couple players who were underachieving and past their due date.

The Wings acquired 21-year old Jimmy Carson from Edmonton. Carson was the prime return in the summer of 1988 Wayne Gretzky trade with the Los Angeles Kings, and delivered under the most extreme of pressures, a 49 goal, 51 assist season in Edmonton, following up his 107 point season the year before in LA. However, Carson was one of the several Oilers who took the brunt of criticism following the first-round playoff loss to Gretzky’s Kings, especially after the Oilers had a 3-1 series lead, only to collapse and be blown out 6-3 in Game 7 at the Great Western Forum. Carson attempted to put a brave face on things, showed at training camp and played the first four regular-season games, but was miserable in Edmonton, and went home in mid-October to wait to be traded.

The Red Wings came calling, but the price was steep. Very. They acquired the disgruntled Michigan native, and tough guy Kevin McClelland (because on a team with Bob Probert, Joe Kocur, Daniel Shank, Torrie Robertson, and even Gerard Gallant, you just can’t afford not to have any fighters handy!), but it cost them former #1 overall pick Joe Murphy, the enigmatic and increasingly erratic Petr Klima, and most unfortunate of all, their 2nd round pick from the 1986 Draft, Adam Graves. Graves was 21 at the time of the trade (mere weeks older than Carson), and though it hadn’t shown on the scoresheet much yet, was starting to thrive with more ice time and responsibility. Though not quite as late a “bloomer” as Adam Oates was, Graves had been in and out of Jacques Demers’ lineup and at times used, far too sparingly, according to many covering the Wings in the newspapers at the time. More on this trade later, although it should be mentioned that young blueliner Jeff Sharples was specifically requested by Edmonton and tossed in as well. But the Wings admittedly had a stockpile of young defencemen all around the same age — Steve Chiasson, Doug Houda, Rick Zombo, Yves Racine — and Sharples might have been the least-promising of the bunch.

As it would turn out, Murphy would play 689 more NHL games with 7 20-goal seasons. Graves would play 1028 after the trade with 8 20-goal seasons, including a 52-goal year and a brilliant playoff in the New York Rangers’ Cup-winning spring of 1994. And Klima, the OT hero of the 1990 Stanley Cup Final, would score 20-plus four seasons with the Oilers, and two more in Tampa, playing 480 games away from Detroit, before bizarrely coming back for 13 games in the Red Wings 98-99 season.

But back to Carson, he made his debut in a highly-anticipated home game against Hartford on November 3rd, in the Wings 14th game of the season. Detroit would lose 4-3 and Carson wouldn’t score. He’d score just one goal in his first six games and after feeling insufferable pressure in Edmonton, THEN coming back to your hometown and being traded for three regular contributors to Detroit’s offense, and popular players at that, the pressure started to build again. Carson would chip in the occasional goal, but it wasn’t what people were expecting from a player averaging 1.18 points/game in his first three seasons.

The Wings would have a catastrophic 12 game winless streak (nine losses, three ties) in which they were outscored a mind-numbing 54 goals against to 29 goals for. At least, fans got to see some scoring, yes? Below are the Norris Division standings on November 17th, the night before the dam burst and the Wings broke the streak with an 8-1 at Le Colisee in Quebec against former teammate-for-a-moment Tony McKegney and the Nordiques.

NORRIS DIVISION GP W L T PTS

Chicago 22 14 7 1 29

Minnesota 20 12 7 1 25

St. Louis 18 9 6 3 21

Toronto 21 10 11 0 20

Detroit 20 4 13 3 11

Over? Well, it wasn’t, but it seemed so. After the disastrous November, the Wings settled in and got slightly better goaltending from the tandem of Glen Hanlon and rookie Tim Cheveldae (Greg Stefan’s NHL career, as it turned out would end following a knee injury in the first period of a late November game at home against Edmonton, necessitating the Cheveldae call-up from Adirondack). December 1989 would see the Red Wings go 6-5-2 overall, and more importantly 5-1-2 in their 8 Norris Division games to bring the pack back closer to them.

Meanwhile, Adam Oates tormented Wings’ management, his former coach Jacques Demers, and Red Wings fans. He merely put up 11 goals and 40 assists for 51 points in his first 34 games playing with Brett Hull, on his way to a 102-point season at the age of 27. Bernie Federko, meanwhile, would score his 10th goal in his 44th game as a Red Wing, putting up only another seven in a lacklustre 57-point season.

Lost in the anger from Red Wings fans about the Adam Oates/Paul MacLean trade, the ineffectiveness of both Federko and Carson early on, was the fact Steve Yzerman was having another incredible offensive season. After posting a career-high (it stayed as such) 155 points in 1988-89 and winning the Lester B. Pearson Award as the top player in the league as voted on by the players themselves, Yzerman adapted to all the turmoil and change within the franchise and continued to score in bunches.

He started the season with 8 goals and 14 assists in the first 12 games and scored 13 points during that catastrophic 12-game winless streak mentioned earlier. All this with the departure of Paul MacLean, Adam Oates, Joe Murphy, Petr Klima, Adam Graves, and the absence of Bob Probert.

Yes, the 1989-90 season can’t be documented without the notation of the late Bob Probert’s incarceration. In early March 1989, Probert was indicted for attempting to smuggle cocaine in his clothing as a car he was in attempted to cross the border via the Detroit/Windsor Tunnel. US Customs agents testified they found fourteen grams of the powder in Probert’s underwear. Probert had suffered through an injury-riddled and personally troubling season but had played the prior six games before his arrest. He was obviously lost to the Red Wings for the remainder of the 1989 season, and it was impossible to guess whether he’d ever play in the NHL again. Prison stints will do that.

Probert spent three months in a penitentiary, three months in a halfway house, and after being paroled and released early, the Red Wings welcomed him back late in the 89-90 season to great fanfare as he scored goals in his first three games back as the Red Wings attempted a late-season playoff run.

On the night of March 24th following a 5-3 win at the Joe against Chicago, the Red Wings had played consistently enough with a six-game unbeaten streak here, and a four-game win streak there, to actually be back in the playoff discussion. The standings below show where the Red Wings stood with just four games remaining, three of them on the road.

NORRIS DIVISION GP W L T PTS

Chicago 76 38 32 6 82

St. Louis 77 36 32 9 81

Toronto 76 37 35 4 78

Minnesota 76 34 38 4 72

Detroit 76 28 35 13 69

Incredible, right? Look at all those ties Detroit put up! From December 1st onward, the Red Wings played thirteen overtime games, won two of them, and tied the other eleven – a big reason they got themselves back in the hunt. Remember, at this point in time, no bonus point for losing in overtime, or the good old days as I call them.

As it would turn out, though, the Wings would lose three of their remaining four games, and the North Stars did enough to hold on to fourth place, winning two of their last four.

The 89-90 Red Wings finished 28-38-14 for 70 points in 80 games. In their final 60 games, they were 24-25-10, but it wasn’t enough to overcome the terrible first 20 games.

Though we didn’t know it then on April 1st, 1990 when the regular season finished, the next few months would see many beginnings and ends. Jacques Demers would be fired as Red Wings’ head coach. Was it the playoff miss and prior 1st-round upset the spring before? The Oates trade? The Carson trade? Both? Or also, the lack of discipline several Red Wings showed before and after the Goose Loonie incident in 1988. Demers would land in Montreal at the start of the 92-93 season as Canadiens’ head coach and the team would win 10 of its 16 playoff games in overtime en route to a very improbable Stanley Cup triumph in 5 games over Gretzky and the Kings.

But another Stanley Cup was about to be handed out, and that same spring, the Edmonton Oilers would go from first-round losers in their first post-Gretzky season to Stanley Cup Champions. They were 3-1 down to the Winnipeg Jets, and from that point forward went 15 wins, 3 losses the rest of the way, beating Boston in the Cup Final. The former Wings forwards, Graves, Murphy, and Klima combined for fourteen goals and fourteen assists, including five game-winning goals. Safe to say, the Oilers don’t win the Cup that year without the Jimmy Carson trade orchestrated by Jimmy Devellano.

1989-90 saw the last of NHL hockey for Bernie Federko, Borje Salming, Robert Picard, Torrie Robertson, Mike O’Connell, Greg Stefan, and for all intents and purposes, Daniel Shank.

Shank became a real crowd favorite, in name alone. He put up 11 goals and 13 assists in 57 games while having several memorable fights against much bigger opponents. He played only 7 games for the Wings the next season, before being involved in a less-than-memorable trade for Chris Tancill.

Bryan Murray was hired swiftly after his firing by the Washington Capitals after their playoff flop of 1990, and with Jimmy Devellano moving upstairs as President, Murray held both head coach and general manager titles.

What a big step forward for the Red Wings, and despite the woeful results in the Oates and Carson trades, Murray gets nowhere near enough credit for stabilizing an aged and teetering Wings team going into the 1990-91 season. Murray drafted Keith Primeau with the 3rd overall pick (behind Owen Nolan and Petr Nedved, and just ahead of Mike Ricci and Jaromir Jagr.). Along with Doug MacLean, a future Stanley Cup finalist as head coach of the 1995-96 Florida Panthers, Murray did an incredible job with Sergei Fedorov as a new-to-America rookie, and got solid production in first full seasons from Johan Garpenlov, Yves Racine, Tim Cheveldae, Brent Fedyk, and even coaxed a 45-point season out of Jimmy Carson, who’d later be traded back to the Kings for Paul Coffey, and Coffey and Primeau eventually would net a return of Brendan Shanahan, and you know how the rest ends.

Maybe the 1990 Red Wings aren’t so memorable for anything other than being the last non-playoff team in Detroit, but with two blockbuster trades that enraged the fans, a future Hall of Famer at centre in Yzerman, a future Hall of Famer quizzically playing his final NHL games as a Red Wing in Salming, and the real life police and courtroom drama that Probert’s situation brought, there was more than enough to keep things interesting.