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What if Uwe Krupp never scored that overtime goal against the Penguins?

Would Jaromir Jagr have ended up in Pittsburgh? What would the Penguins have been able to do in the 1990 playoffs?

Player Mario Lemieux

The Pittsburgh Penguins have no shortage of “what if” scenarios in their franchise history, including a couple of infamous Game 7s (New York Islanders in 1993, Florida Panthers in 1996) and the health of the two greatest players in franchise history (Mario Lemieux and Sidney Crosby).

For now, let us focus on one that looked crushing at the time, but ended up being one of the most significant — and franchise altering moments — in team history.

That moment: Uwe Krupp’s overtime goal for the Buffalo Sabres in the regular season finale of the 1989-90 season.

If you are not familiar with the situation, it played out like this.

The Penguins needed just one point in the regular season finale (a win or a tie) to clinch a playoff spot. They were a playoff team the year before (the first playoff appearance for the team with Lemieux) and were a Game 7 against the Philadelphia Flyers away from being in the Wales Conference Final. Lemieux was just starting to hit his prime, there was a strong core of players being built around him (including Paul Coffey, Mark Recchi, and Kevin Stevens), and they were generally seen as a team on the rise in the NHL.

This would also be the first season that Lemieux would miss significant time due to injury, appearing in just 59 games during the regular season (still scoring 45 goals and 123 points). Those missed games would obviously play a pretty significant role in the Penguins’ spot in the standings heading into the regular season finale (they badly struggled without him down the stretch), but they still had a chance to make the playoffs with a tie (or a win). They would also be getting Lemieux back in the lineup for the first time after he had missed the previous month-and-a-half. He recorded two points (the Penguins only scored two goals), including the game-tying goal early in the third period.

Everything was right there for them, especially once they reached overtime and simply needed to avoid giving up a goal.

But just one minute into overtime of the regular season finale, Krupp beat Tom Barrasso to give the Sabres a win, send the New York Islanders to the playoffs, and keep the Penguins at home.

There are a lot of what ifs at play here, including what would have happened had the Penguins actually made the playoffs during the 1989-90 season. It is an intriguing question, not only because of how far the team had advanced the year before, but also because it was playing in a very winnable Patrick Division where they would have had a legitimate chance to beat any team they were matched up against.

A tie against Buffalo would have given them a Round 1 matchup against the New York Rangers in the playoffs. Even though the Rangers finished the regular season with the best record in the division, they were hardly a juggernaut of a team. Their 86 points were 8th out of 21 teams in the league, while their 36 wins placed them 12th — just four wins ahead of the Penguins. It would have been an extremely evenly matched series that could have gone either way.

There was also this fact: In the head-to-head matchups during the regular season the Penguins went 5-1-1 in the seven games that Lemieux played in, while he recorded 16 points in those games. They absolutely could have won that series. Had they done so would have found themselves in a Round 2 matchup against an even more beatable Washington Capitals team (a Capitals team they went 5-2 against with Lemieux in the lineup that season).

It is not beyond the realm of possibility to think that the 1990 Penguins could have found themselves in a Wales Conference Final showdown with the Boston Bruins before potentially getting a chance to face Edmonton Oilers dynasty in the Stanley Cup Final.

Obviously that is a lot of what ifs, but that is the whole point of a “what if” exercise. And quite honestly, that Penguins team — with Lemieux in the lineup — beating the Rangers and Capitals seems very, very, very reasonable.

The downside to all of that would have been what it meant for the Penguins that offseason and the long-term direction of the franchise.

Because they missed the 1990 playoffs they ended up with the No. 5 overall pick in the draft where they selected Jaromir Jagr. Had they gone on an extended postseason run they may have picked too late in the first round to get him.

Jagr, of course, would go on to be a franchise cornerstone, an all-time legend, and a massive part of the first two Stanley Cup winning teams in Pittsburgh.

Selecting him is one of the biggest and most important moments in the history of the franchise and almost certainly helped produce two championship winning teams.

Had Krupp not scored that goal the Penguins would have had the chance for a lengthy playoff run in the spring of 1990 (which would have been exciting and intriguing). But it also would have kept them from getting one of the most significant players in league history, potentially kept them from winning the Stanley Cup the next two seasons, and having the most dominant offensive duo the league has ever seen (all of which would have been bad!).

Put it all together and it makes Uwe Krupp one of the most meaningful players in Penguins history, even though he never actually played a game for the team.