I'm not sure they'll be a taker for that trade, given how this draft seems to have a dropoff around pick 12-14.
But based on past trades, including the ones listed above, I actually do think it's potentially possible. I'm also remembering the Coyotes recently moving up from #27, #34, and #45 for pick #11 to take Conor Geekie. So generically a similar trade would be #20, #34, and #58 for pick #9 or #10.
2 things needed to line up. Coyotes having the extra picks, which CHI does have and SJ sorely lacking picks having acquiring EK and making a lot of win now moves.
I mean, just looking at the top 10,
SJ, Chi, Ana, Cbs, AZ, Mon, Ott are your bottom 7.
I don't see any of the other 6 looking to add more prospects to their pool by moving out from the top 7. Those clubs have been at the bottom for a couple of years now, so quantity isn't what they are seeking.
So, down to 8-10 picks.
SEA, PItt, Cal, Buff, NJ hold slots 8-12 currently.
Sea, I think they bet on the higher pick turning out than 20 and the extra.
Pitt, No top end talent and have to decide whether to give his pick up or risk the unprotected 2025 pick to SJ.
Cal, they already have Van's 1st, so no need for them to drop to 20.
Buff, they are more of a we need guys who can help us now than adding picks.
NJ, they are better off using this pick on player or trading it for now help since Hughes is on his great 2nd contract. No real need to drop down.
So, if we talk more reality, I don't see much reason for teams to go down to 20 for additional picks.
Again, NFL vs NHL view 2nd rounders much differently when it comes to draft day trades. You're getting guys now in the NFL vs waiting 2-4 years for 2nd rounders to play. GM who trades down might not be around for those extra picks to arrive.