The Penguins won in 2009 because they had Malkin on an ELC. They won the last two years because Crosby, and to a lesser extent Malkin, are on very cap friendly deals they signed to help the team.
Chicago won because Toews, Kane, and Keith all had long terms deals for reasonable money. They didn't get paid big until they had won 3 cups.
The Oilers will never have that same window to put together a mini dynasty. All chance of them becoming the next Penguins or Blackhawks dies with the McDavid and Draisaitl contracts (assuming the rumors are true). It may still be possible to win a cup at some point, but it will take an absolute perfect storm of great depth players on low paying deals and young players breaking out while still on ELCs. I hope I'm wrong, but I bet the Oilers will not win a cup over the course of these contracts.
Yep Connor and Leon can have their money, but they can't have their window of a mini-Cup run early in their careers.
It's either one or the other (sacrifice). Doesn't work both ways.
Blackhawks and Kings won multiple Cups but on a salary structure that had multiple good players in the range of 5-6 million dollars and a roof for 7 mill or so for anybody.
Penguins only won once with Malkin, Letang, and Staal on cheap ELC deals, otherwise Crosby doesn't win a Cup until his
11th year. Think long and hard about that Connor, you could be waiting that long very easily.
You see a Evgeni Malkin for 3.8m on that Oilers roster? How about a Jordan Staal caliber player to 2.2m? No? Then stop with "yeah but Crosby ..." crap. Yeah but Crosby would be waiting until year 11 if he didn't cash in with a cheap roster, you do not have that luxury Connor.