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So I‘m finally getting to run Darkening of Mirkwood - one less thing on my bucket list.

Now, when Bard starts to woo Una he will send the fellowship to Erebor. They‘re supposed to cash in his favour for returning the Arkenstone and demand a piece of jewellery fitting for a queen. The dwarves will agree on giving him a certain item, which will cause trouble with one individual who believes that it should rightfully belong to his family.
However, the players will also be warned that Smaug‘s taint may still linger on the piece. I want to use this as a possible explanation for all the ill that befalls Una and Bard later on, but I‘d also like to give the players an opportunity to break the curse.
Problem is, I have no idea right now how that could work. Time is short, so visting Elrond or Saruman is not going to work (it‘s unlikely that any character will have connections to these people anyway).

So, how do you break the curse of an ancient malevolent dragon upon a piece of magnificent dwarven jewellery?

The only curse placed upon Smaug's treasure by the dragon himself seems to be the dragon-sickness, and that is simply a function of the hoard being in long possession by a great worm. Any one part of that hoard only carries a tiny portion of that taint--though an elaborate piece of expensive jewelry is bound to carry more of it than a single gold coin. The best cure for Smaug's curse seems to be simple generosity, reminding me of Tom Bombadil taking the contents of the barrow where Frodo and his companions were imprisoned, and spreading it out for any passerby to take. The mere act of giving the piece freely as a gift might go a long way towards cleansing the taint from it. Perhaps the dragon-curse can be broken for good by removing a piece from the item, fashioning it into a ring or pendant or some other item, and gifting that portion to someone else. However, the nature of the dragon-sickness doesn't seem to have much to do with the later sorrows of Bard.

Perhaps this item of jewelry should have its own sad history that lays a second curse upon it that brings misfortune to its possessor--a curse that has nothing to do with Smaug.

Thanks, that’s excellent input. I had the dragon’s curse filed under “bad stuff happens” in my head, so thank you for reminding me that it’s actually greed-related stuff in effect.

Well, I’ve already mentioned that there is another dwarf who thinks the precious should belong to his family. He just can’t prove it to the council. So with some added tragedy in the past, like the last owner sacrificing herself to save her beloved’s life, there might be enough substance here for another curse.

In that case breaking it might be tied to how the fellowship deals with their adversary. Compensating him or even convincing him to give it up freely (“It will be worn by a queen again - that’s what it was made for, wasn’t it?”) will cleanse it. Taking it by force of law or, even worse, arms will make it carry the grudge of a whole clan of dwarves.