His contract makes his value more of neutral worth nothing tbh. like Bobby Ryan dude is overpaid, but 50 point pace retained worth something. So Oshie retained is worth a mid-round pick

No he has value for sure

He's pretty damn far from what I'd deem negative value - guys like Lucic or Seabrook who are actively bad and expensive. BUT he's got the worst cap hit on the Caps and he's probably the most obvious candidate to have a pretty steep decline because of concussions and how he plays.

Right now, he's an overpaid 50 point winger who brings a ton of intangibles and can wear a lot of hats for the Caps. But in a few years, I could see his contract being a problem. I wouldn't say hes even an asset for the club because there's basically zero chance he's moved in the near future.

He definitely has value now for teams going for a Cup over the next few years. But in about 3-4 years his value goes down due to the contract. But all of this is mute because I can't see the Caps ever wanting to move him. MAYBE they let him get taken in the expansion draft.

This. And even then, Caps would probably have to really tank next year and completely give up with the current core to expose Oshie.

Mostly the same as what others have said - not negative trade value per se, but he's close to unmoveable when you put together what he brings to the table for the Caps on/off ice and finding suitable trade partners who would want to take on an aging winger and give up true value in return. I.e., probably just not a lot of teams with the cap space to take on his contract that are not actively rebuilding and therefore aren't seeking somebody with Oshie's age, contract, and skillset, except maybe to mentor younger players, and then there are cheaper versions (even if they don't have similar production).

Not quite what you asked but a question that also gets tossed around a lot is "does Oshie have a bad contract" or "is Oshie's contract worth it". On its face, you could make an argument that it was a bad contract to give an aging winger (although there are certainly worse ones out there), and you might have a point - an 8-year contract for a 31-year-old winger that took up about 8% of the cap in the year it was signed is a little rough, but he was also coming off a season where he was within 2 points of guys like Eichel, Toews, Giroux, & Forsberg. Plus they won a cup, so that makes everyone likely to forgive a lot.

Depending how confident the Caps are that their team can contend with or without Oshie, I could see either of the following being interesting:

Lucic+1st=Oshie..... Caps get a pick to take on the ultimate project.

Oshie+2nd+3rd+Bowey=Zucker. Get younger with the same skill level, for a price. Minnesota adds a third big star off Team USA, to help lead and mentor their team, but more importantly, picks and a young player.