Fair points, but none of our pass rushers have panned out. The two that have were the rotting corpses of Johnathan Abraham and Dwight Freeney on short-term, placeholder for retirement contracts. Also, it's difficult to find a suitable pass rusher late in the first round or in the ensuing rounds. Likely, if we make that trade, we're trading two picks that are between 21-32. If you can get a guaranteed top-tier pass rusher, it might be worth it.
Now, if we were still picking in the Top 10 year in and year out, my opinion might be different.
Yes, there is some risk, but I don't understand thinking it's not worth it. Miller was a sack machine long before Ware joined the Broncos and he's only been in trouble with the league one time, that being in 2013. With two late round firsts, are you going to get a player of his caliber? Are you even guaranteed two starters? One starter? We got DJ freaking Humphries this year. How much of an impact has Jonathan Cooper made? A bird in hand is worth two (or more) in the bush. Easy trade for me to make. Professional sports is about quality over quantity. Only so many guys can be out on the field at one time. I'd rather have one Von Miller than five Markus Golden's.....and I like MG.
Theres other factors beyond just "we're getting an elite pass rusher", because you must also pay him. Likely top paid defensive player in the NFL money. Talks are upwards of 127 million. Deals like that absolutely hamstring you. How do we resign Tyrann, CC, Veldheer, whoever-else, when the time comes when we are paying a non-QB QB-type money? And that's on top of the point already made about the fact hed be our ONLY pass rusher. Teams would walk in here, double team him for 60 minutes, and walk out. How would you feel if our 100M pass rusher ended the season with 5 sacks because he got doubled every game? And CC/Golden have not consistently shown they can win 1 on 1. That's a major problem. Wed be wasting money on essentially a block sponge NT at the OLB position.
Lastly, we haven't tried drafting yet. We've spent 1 pick on a pass rusher lately, Golden, and while hes not Von Miller, statistically, he was the best rookie pass rusher last year.
I know we don't like need-drafting, but going after a pass rusher in 1, 2 and 3 might not be a bad idea. One is BOUND to be good, as Keim is generally a good drafter.
*lastly part B, you don't need a Von Miller to win the superbowl. It helps, big time. But its not a requirement. Von Miller, JJ Watt, Aaron Donald, Khalil Mack are rare. All A++ guys.
But to win the superbowl, Id say you need 2 B+ pass rusher. Those are much easier to find then all-timers/future HOFrs like the guys I named.