I think Jerry should do this. Yes, Wilson is older, but he's better than Dak, and with a lower cap hit, it makes sense, but there are some IFS.
1. Do it if you can get Wilson for Dak plus our 1st-round pick. No giving up two firsts; that would be too much.
2. This team must do everything possible to build up this defense. I'm not sure if the following is possible, but I would prefer the trade to be Dak, plus our 2022 first rounder, leaving us with the #10 pick this year to draft the best defensive player available. Like I say, that might be a reach, so my second choice would be the 2021 first rounder + Dak for Wilson; then with the #1 pick in 2022, you go for the best defensive player available.
3. Either way, most of the 2021 draft should be about defense.
4. Re-sign Dalton, if possible, to back up Wilson. If Wilson goes down for a few games, I would much rather have an experienced vet to give us a better chance to win than a rookie project would.
5. Do some smart free agent shopping. Wait until after you have some idea what you've gotten from the draft, and see if you can sign an experienced game changer on defense, much like the Bucs signed Suh. It may be a great D lineman or it may be a great safety. But you build up that D primarily through the draft and then add the right vet to help them be their best.
6. You don't bargain basement free agent shop for key needs. You bargain basement shop for basic needs like punt returners, other special team needs, maybe a backup running back, and other backup positions.
7. Work up some unexpected, occasional use plays in the offseason. These are not your core plays, but rather occasional use ones that you only use unexpectedly to turn the momentum in key games. Have in your hip pocket plays like the direct snap to a running back, the flea flicker, a halfback pass to your QB downfield as a wide receiver, reverses, end-of-half Hail Marys, etc. Like I say, you don't get cute by over-using these things. You establish a sound game plan, but as the opponent gets used to your conservative play, you throw in an occasional surprise, especially when you sense you can catch them off guard.
8. Waiver wire sniffer. The WW is often a long shot, but you can add helpful players from it. Especially be aware when another team gets overstocked at a position and thus can't sign everyone of value at that position. This was how we ended up with an excellent #2 WR in Laurent Robinson some years back. Obviously, you can't build your team from the waiver wire, but an astute coach can fill an occasional need from it.
Okay, I ended up writing way more than I had planned to. But anyway, in short I'm a "yes" on going after Wilson provided we do it right.