What are the odds McDavid plays his entire career in Edmonton? Let’s say he doesn’t win a Cup in EDM, demands a trade or leaves in free agency, and ends up on pretty much any non-Canadian team. Would his Young Gun or any other rookie card be worth even half of what they are right now?
That may be the case.... the team continues to falter.... and he leaves Edmonton when this contract is up (or before, if he asks to be moved).
For a LONG time, it seemed that generally when players left their original team, RCs almost never maintained value. This was certainly true for Canadian Teams, Original 6, and the other "big" teams in the USA.... granted, lower valued players might also get a spike in value if they went to one of the more popular teams.
Assume the Oilers have annual playoff teams, start winning rounds again (McDavid-era Oilers have gotten out of the first round once) - I think the threat of him leaving because "the team hasn't won" is overblown.
Look at the best players from the last 15 years (I'm removing McDavid from the conversation). The top three IMO are Crosby, Ovechkin, and Kane (put them in whatever order you want). All three have remained with the clubs that drafted them - and I suspect all three will retire with those clubs.
If I continue to go down the list of the top 20 scorers from the last decade... after those three, the list has McDavid, and 10 more guys that haven't changed teams (and I don't think will be, anytime soon):
Marchand, Giroux, Backstrom, Malkin, Kopitar, Benn, MacKinnon, Kucherov, Stamkos, Bergeron
Here's the remaining 6, who have changed clubs:
Tavares, Wheeler, Kessel, Voracek, Seguin, Pavelski
Kessel (3), Voracek (2), Seguin (1) have only been traded, they've never left via FA (I would imagine that will change soon with both Kessel & Voracek).
Tavares left as a UFA, same with Pavelski. Wheeler is a mixed bag: He never signed with the team that drafted him (ARI), and signed as a free agent with Boston. The Bruins traded him to ATL, who moved to Winnipeg, and he's been there ever since. He's into his 10th season as a Jet now - and wasn't an elite player before he got there.
I was only looking at points, so defenseman were left out of the equation.... but just to add a few more names to the mix, I'd argue that the best dmen of the last 10 years are some combination of:
Hedman, Carlson, Doughty, Keith, Burns, Karlsson, Josi, Letang, Peiterangelo, and Weber.
Peiterangelo is the only one of those guys to leave via free agency.... three others (Keith, Burns, Karlsson) have were traded (Keith, well past his prime, and Burns - really before he was considered elite).
All I'm doing here is showing that most of the truly elite players in the NHL have not actually left their teams via free agency, or demanded a trade.
I grant you, many of the names I listed have won Stanley Cups - so perhaps the pressure to leave, and chase a ring isn't as great.... but I think it has a lot to do with guys establishing themselves as a player with a particular team, and really having personal ownership on that team's results. You play for a club, you play in a city - and so long as you're treated well: For the most part, Superstars aren't looking to leave.