To be clear, I am not recommending this approach but rather raising it as a possibility.
In the NHL as it currently stands cap space has value if you can use it. Let's assume the Oilers can use it and that therefore it is worth something to them.
Our mission: the Oilers aren't winning the Stanley Cup this year and don't have the core to immediately contend. Rather than go through a painful 5 years and waste Ales Hemsky's contract entirely, let's reload instantly and make a new team.
Remember; in this reality cap space has value, so view all trades in that context.
Dustin Penner to someone for a draft pick.
Steve Staios and Ethan Moreau to a contender for a pick and a prospect.
Robert Nilsson for a young defenceman.
Erik Cole for a draft pick (note; in this type of thinking, trading Cole actually isn't a huge priority because he's off the books regardless)
Marc Pouliot for a 4th rounder or a similar prospect with a different skillset.
Zach Stortini traded for a better hockey-playing version of himself or a pick.
Strudwick is not resigned.
Jacques is released or bought out.
Roloson is not resigned. He's traded to a contender if possible.
So here's what we're left with:
------- ------ Hemsky
Cogliano Horcoff Pisani
------- Gagner -------
------- Brodziak -------
Still in the mix/on the bubble: Schremp, Brule, Potulny, Lefebvre, Reddox, MacIntyre
I like our D, they're quite good. Sign a different vet to play #7. But make him actually be the #7 and have SOME exceptional asset rather than just being BLAH.
The role of goalie is open.
There...cap space galore and freedom + a butt load of picks that can be swapped for players.
Conklin (so sue me; he's a good goalie and deserves to make things right here!)
I'm not a big fan of spending a lot on goalies because I think it's a lot more of a crapshoot than many others do. I'd also be looking at Antero Nittymaki or a trade for Chris Mason who's signed for another year at 3 mil. For you Conklin haters: 22 wins, 6 SOs, .918 save percentage and Osgood isn't even close. He's a good goalie.
D stays pretty well the same as I noted.
Cammalleri (he's still the right guy for the job a year later. Backup would be Havlat)
Connolly (won't get a huge deal because of past, which is overblown. So skilled. Backup plan would be a trade)
Cogliano-Horcoff-Pisani (This puts Horcoff in an appropriate role and gives him solid guys to play with. I like Cogliano's speed better coming off the wing).
Bell (Take a chance on someone like a Mark Bell for this spot. Our Bubble guys could also compete)
Gagner (can't give up on this kid. Don't do it. He will be EXCELLENT)
Guerin (tutor the kid, provide toughness, shooting, leadership. Backup here would be to try to get Sykora back and get a big guy for LW)
Ian LaPerriere (He can shoot and is a pain in the butt to play against)
Kyle Brodziak (Kept, I really like his game)
Chris Neil (No-brainer)
There...now we're harsh to play against, can shoot the puck, and have an offensive unit to play with Hemsky. Am I under the cap? I have no idea. If I'm not, shave on the fourth line.
So that would be my plan if we were down for tearing the place to the ground.