Edmonton Oilers Leon Draisaitl (29), Evan Bouchard (2), Connor McDavid (97), Zach Hyman (18) and Ryan Nugent-Hopkins (93) celebrate Hyman’s goal against the Los Angeles Kings in Game 2 of their 2024 Stanley Cup Playoff series at Rogers Place on April 24, 2024, in Edmonton. Photo by Codie McLachlan /Getty Images

But the Chicago Blackhawks won zero Stanley Cups from 2016 to 2020, all with Kane and Toews still in their prime.

What went wrong? And can Bowman avoid the same fate now that he’s GM of the Edmonton Oilers, a team that has yet to win a Stanley Cup in the prime years of Connor McDavid and Leon Draisaitl?

Spoiler Alert: Yes, the Oilers can, but the next few weeks are critical when it comes to finding the right solution. Much of it comes down to the direction and conclusion of Draisaitl’s contract negotiations, both in terms of the amount and term of Draisaitl’s contract, and the example it sets for future negotiations with Evan Bouchard and Connor McDavid.

Bowman’s mistake in Chicago

Stan Bowman twice signed Kane and Toews to big contracts, once the deals working out in terms of Stanley Cup victories, once not at all.

Bowman was integral to the building of the Hawks, working his way up from Director of Hockey Operations in 2005 to Asst. GM in 2007 to GM and VP of hockey operations in July 2009, a job he held until 2021.

In December 2009 he made a move that was critical to the success of the Hawks, signing up his two young superstars Toews and Kane, to matching five years deals at $6.3 million per season, which then represented 11.1 per cent of the NHL salary cap each, 22.2 per cent combined, giving Bowman adequate cap space to build around them.

It wasn’t enough cap space to keep all of Chicago’s fine young players. Bowman had to move on from aggressive wingers Andrew Ladd after the 2010 Cup and Troy Bouwer in 2011, along with goalie Antti Niemi, skilled winger Kris Versteeg and  big and talented Dustin Byfuglien after the 2010 Cup. After the 2013 Cup, checking centre Dave Bolland also left. Skilled d-man Nick Leddy was traded in 2014.

Skilled winger Brandon Saad and savvy d-man Johnny Oduya went after 2015 Cup, along with rental centre Antoine Vermette.

But the big issue came when Kane and Toews signed their third contracts in July 2014, the two contracts to kick in for the 2015-16 season at $10.5 million each, 15.22 per cent of the cap each on their signing day.

Essentially, the Hawks went from paying 22.2 per cent of the cap to the two players to 30.44 per cent of the cap to them.

Never again did Chicago make the Stanley Cup Final, losing such players as  skilled wingers Teuvo Teravainen and  checking centre Andrew Shaw in 2016 and future superstar Artemi Panarin in 2017.

Of course, Bowman didn’t always spend his money on the right players. And he didn’t always get a great return on his trades. But I’ll suggest a major issue was the high cap hit paid to the team’s two superstar players, especially when their third contracts kicked in, taking almost one third of the cap.

As great as Kane and Toews were, Chicago was limited in how much support it could provide them because of the team’s salary cap issues.

I wonder if you asked Kane and Toews if they were to do it all again if they would have agreed to take less money in 2015 in order to give Chicago a better chance of winning more Cups. It’s a tough question, and there’s no shame in taking the money. I hold it against no player if he decides to take more money in another NHL city rather than take a discount on a team that might win a Stanley Cup.

The Stanley Cup Discount

A number of players have now reportedly taken less money to sign in Edmonton so that they might win the Stanley Cup. That number almost certainly includes the entire third line of Adam Henrique, Connor Brown and Mattias Janmark,  as well as top free agent signings, Jeff Skinner and Viktor Arvidsson.

But the biggest issue for the Oilers is getting Leon Draisaitl, Evan Bouchard and Connor McDavid to sign new contracts here, while still having enough money left over to sign enough good players to compete for the Stanley Cup in coming years.

Right now the talk is that Draisaitl is looking to sign for eight years at between $13 million and $14 million per year in salary. At $13.2 million per year, Draisaitl would be taking 15 per cent of the cap as it stands now. If McDavid signed for a similar amount, that would mean the two combined would be taking about 30 per cent of the cap, about the same as Toews and Kane after 2016 when Chicago was no longer able to compete for the Cup.

But if Draisaitl were to take a Stanley Cup Discount of 13.5 per cent of the cap, he’d be paid $11.88 million per year. He and McDavid, if he took a similar amount, would combine for about 27 per cent of the cap.

It’s unlikely they will take such a Stanley Cup Discount, at least if you go by the constant drone of the rumour mill that has Draisaitl taking more than $13 million per year in a new deal. But, make no mistake, if Job One is to win the Stanley Cup, trying to convince his star players to sign is Stan Bowman’s most crucial task, but convincing them to take some kind of Stanley Cup Discount is almost as critical.

Again, if Draisaitl and/or McDavid were to head to the open market and free agency they could likely command 20 per cent of the cap on a seven-year term.

But if they want to play together and challenge for the Cup year after year, Bowman’s job is to convince them their best bet is Edmonton with Stanley Cup Discount contracts. He can certainly bring up his Chicago experience in that conversation.

Draisaitl will make a key move in Edmonton’s quest for a Cup in these contract negotiations, of that there is no doubt.

It will be a difficult choice if he turns down millions, but as much as I’d love to see him get as rich as possible, I’m also an Oilers fan. I’m hoping he both signs here, makes a boat load of money, but also sets the standard for the team by taking a Stanley Cup Discount.