There's one thing you're forgetting...

[Eltern]

I'm Captain Jack Sparrow!

I'm making a character with Jack Sparrow's mentalitly (from Pirates of the Carib.), and I'm having difficulty with adapting him to a world filled with magic. He is NOT a swashbuckler, he's actually a knifethrowing enthusiast, but the personality and style is the same. However, as a Chaotic "Goodish" character with a good sleight of hand skill, my DM is going to try to cow me into staying in line by utilizing the magic system. For instance, he's working in my character by having me delivering some blue armor from wherever, and then I meet up with the party. Now, I think I'd probably sell off the armor somewhere else, then tell my boss that his competitor stole it from me, sparking a merchant war, from which I will find a way to make a profit and such. However, now he's saying that I'm having dreams where a guy pops up and says "If you take the armor, you will suffer the consequences." How does a Captain Jack Sparrow react to those kind of big guns?

Thanks,
Eltern

 

[RangerWickett]

He sells it, right proper, then steals it 'imself and sells it again.

 

[Eltern]

He sells it, right proper, then steals it 'imself and sells it again.

While that was something else I considered doing, it still doesn't address the fact that in J. Sparrow's setting, it's feasible for him to screw with the powers that be, because they are not THAT much higher in power than he. But in Greyhawk, he's doing the cha cha with powerful wizards. In this situation, it's logical that he'll get his arse blasted if he tries to steal it again. Does he back down, or go for it in high flamboyant fashion?

Thanks,
Eltern

 

[Tilla the Hun (work)]

While that was something else I considered doing, it still doesn't address the fact that in J. Sparrow's setting, it's feasible for him to screw with the powers that be, because they are not THAT much higher in power than he. But in Greyhawk, he's doing the cha cha with powerful wizards. In this situation, it's logical that he'll get his arse blasted if he tries to steal it again. Does he back down, or go for it in high flamboyant fashion?

Thanks,
Eltern

Sounds to me more like your gm is stepping on your character concept - possibly due to you not communicating what Jack would do in the situation?

Be that as it may - deliver the goods as is proper, collect your money for delivering it. Once the PTB's don't have their full attention on you, meet with the local underlife to steal the armor back and re-sell it.

Better yet, after the focus is off you, get with a kender (you said Greyhawk ), and explain it to me in a typical 'Jack Sparrow' style and let 'him' get that suit of armor for you...

Flamboyant, extravagant, devious, and underhanded...

Make the delivery -with- your new found kender. Gently encourage him when making the delivery. During the ineveitable chaos, steal the armor back and hide it immediately. Find it and collect the finders reward. Repeat the performance, only this time, have a fence collect it and pay you money.

3x the money income just for the fun of it