You need 2-3 Superstars and another 2-3 stars in their prime / near prime to win the cup
How you get those players is irrelevant BUT what is relevant is the odds of acquiring them
Trades : Eichel and MT are the last two superstar quality players to be traded and both demanded a trade, AND wanted to go to a contending team. The odds of Calgary acquiring a star player this way is very very low, because teams genuinely don't trade them unless forced too, and then they usually go to winning, desirable locations.
Recently Reinhart would also fit into this group (and Fox but that's another outlier a team like the Flames certainly can't rely on)
Guys like Montour, Filip Forsberg, Mark Stone, Kadri also helped push teams over the edge / stars seasons who were traded
FA: Oof. If you are looking for franchise foundation FA's you are going to have a bad time.
Panarin is the best UFA recently, with guys like Hyman, Pietrangelo, Bobrovsky, JT Miller, Taylor Hall (for a few years), Zibanajeb, O'Reily rounding out the best FA signings
UFA's usually cost too much and are post apex. But its doable to find a foundational piece once in a while, but you better have a solid core first IMO
Draft Them: This is how most competitive teams acquire their core. (Duh)
Below is the success rates per round and per pick. For no surprise, picking higher means better chance at success - But I don't think people understand how huge the drop off actually is
https://thehockeywriters.com/success...l-draft-picks/
Drafting top 4 gives you a ~13% chance of a player who gets 1000 career points (Superstar Level Player)
Drafting 10th? 1.6%
Drafting 24th - 32nd? ONE player - Joe Nieuwendyk (CGY)
I know people like to point to JG's and Kucherov's as example - The odds of drafting a 1000 pts player in the 4th round is 0.3%. It's happened 5 times.
Even lowering to 750 points (star quality player) it has happened 3 additional times.
Looking at the Flames right now I see Wolf (fingers crossed no jinx) as potential star quality. I think you might get one more player out of the prospect mix who ends up in that group/ you hope you do
That means we need 2-3 more stars in our pipeline. (And preferable 1-2 superstar calibre)
It isn't just that the Flames need to draft better then the rest of the league, it's that statistically players of star quality very very rarely drop past the first few picks of the first round to even be available to be picked. And with better analytics these outliers will occur less and less
(I know this doesn't account for D or "non points" measures although GP is also in the link. It is more illustrative to show how rare drafting a superstar forward outside the first few picks really is)