Back in the final season of the World Hockey Association, 17 year old prodigy Wayne Gretzky joined the Indianapolis Racers. Eight games into the season, Racers owner Nelson Skalbania wasn’t seeing the results he needed in his wallet and decided to sell Gretzky (along with two players) for $850,000. Skalbania told Gretzky he would be traded, but it could be to either Edmonton or Winnipeg. Gretzky was put on a plane with the other two players, Eddie Mio and Peter Driscoll, without knowing where their final destination would be. In the end, the Oilers made the deal.
Both Edmonton and Winnipeg were absorbed into the NHL a year later, and both teams were dismantled thanks to the NHL’s dispersal draft, which essentially punished the four new teams. They also selected at the end of the entry draft, instead of the beginning like expansion teams normally do. Fortunately for Edmonton, they were allowed to protect Gretzky as a priority selection before the expansion draft.
But what would have happened if Skalbania made the deal with Winnipeg instead?
While both teams struggled in their first NHL season, 69 points for the Oilers, 51 for the Jets, Gretzky surely was the difference between the two teams, scoring 51 goals and 137 points, winning his first Hart Trophy. According to Hockey Reference’s Point Share system, Gretzky had about 13 that year, which would give the Oilers 56 points and the Jets 64 (and give them the final playoff spot).
The next season, the Jets were the worst team in the league by far (32 points to Detroit’s 56). Gretzky would have made the team better, but not that much. In the next draft, the Jets selected Dale Hawerchuk #1 overall, giving Winnipeg a 1-2 punch down the middle or putting Hawerchuk on Gretzky’s wing.
While the Jets and Oilers were dismantled in the 1980 dispersal draft, the Oilers restocked their team through the NHL Entry Draft with names like Messier, Kurri, Coffey, Anderson, Lowe and Fuhr. The Jets selected decent players, but could have made better picks (Ken Daneyko instead of Jim Kyte, 1982 or Cam Neely instead of Andrew McBain, 1983). Despite these picks, the Jets regained prominance in the mid-1980s behind Hawerchuk, Thomas Steen, Paul MacLean and Randy Carlyle. MacLean and Carlyle were both acquired via trade.
Fast forward to alternate reality 1984-85. The Jets finish ahead of the defending Cup Champion Oilers and win the Smythe Division for the first time by 10 points over the Flames, with the Hawerchuk-Gretzky-MacLean line finishing with 167 goals, 439 points. Edmonton finishes third, four points behind rival Calgary. However, the two meet in the Smythe Finals, Winnipeg makes its’ first conference final with a six game series victory. Behind Gretzky and Hawerchuk, the Jets defeat Chicago in game seven to make it to the Stanley Cup final, taking on the Philadelphia Flyers. The young Flyers find a way to solve Jets goalie Brian Hayward and even Gretzky can’t stop the Flyers from winning in seven games.
The next season, the Jets struggled in the standings. Gretzky won his seventh straight Hart Trophy, but the team failed to get out of the first round with a loss to the eventual Champion Flames. In 1987, the Jets rebounded and finished in first place again with 105 points, beating out Calgary’s 95 and Edmonton’s 89. Winnipeg and Edmonton meet in the Division Finals once again, with the Oilers beating the Jets this time in seven games. The Oilers went on to the Cup Finals once again before losing to the Flyers in seven.
Gretzky failed to play 65 games for the first time in his career in 1988, and trade rumors started to swirl. The Jets still finished in second place to Calgary, and beat out Edmonton in the first round. However, they were no match for the Flames as Calgary won the series in six games and went on to win the Stanley Cup over Boston.
Two hours after the Jets’ exit from the playoffs, Gretzky learns about the Jets’ plans to trade him, citing growing salaries in the NHL, crunching owner Barry Shenkarow’s wallet. This would eventually force the team to move to Phoenix in 1996. Gretzky would be dealt to Los Angeles, where he would make one last Stanley Cup Final appearance in 1993.
The Flames and Oilers would split the next two Stanley Cups, each defeating Gretzky’s Kings in the Divisional Final. The Jets failed to make the playoffs in 1989 and lost in the first round in 1990. The Jets never finished higher than fourth in their division until after they had relocated. After Messier left Edmonton as a free agent, the Oilers would toil in the bottom half of the standings for the next few years, prompting the trades of many veterans including Kurri, Coffey and Anderson.
Gretzky retired in 1999 and later coached Phoenix, coming back to the team he started his NHL career with. While he collected many trophies and set various records, he missed one major thing his career needed: a Stanley Cup.