D&D 5E {Roleplay Help} The Swashbuckler

[Allistar1801]

Last week my friend decided to run a 1 shot of an island adventure, and we actually ended up loving it so much that we're probably going to continue it as a full campaign! This kind of left me in an awkward position as to what I wanted to do with my character, and I figured why not post about it.

Stop me if you've heard this one before, a charming Italian sailor who's quick with a joke and the jab of a rapier. Yeah I went with a rogue, but I wanted put a little spin on it by making him a bit of the classical braggart with an aura of swagger to him. Also since my alignment I decided to be a bit of a generous man, still a bit snarky and whatnot but a kindhearted underneath it all. The only thing is I rolled pirate for his background rather than sailor, and I think that's running a bit against how I played him throughout the session. I can't really change it since it's kind of cannon now since I rode in on a rowboat with them. I however did lose them pretty quickly by pulling a bit of a Jack Sparrow and completely ignoring the dock marshal and letting the rest of them handle it, meanwhile I slip away to mingle at the festival in town meeting up with the other party members while I'm enjoying the sights of this new foreign land. I never used my background feature and from the way I want to play my character I don't think I ever really will, so how can I RP around it?

My first thought is having him try to escape it and pursue his own journey (Twas one of his ideals). Trying to shake the bad reputation and become a captain in his own right seems like a neat way for me to go. Only problem I see here is the fact that he doesn't really have anything to run from. The islanders are nice, and he's nice to them, the other pirates are pretty much the only ones that know about it, and it's not like he's proving anything by giving them a middle finger. It changes nothing in the eyes of the navy or the islanders, but it would be so unbelievably true to the character. Perhaps I can work with the DM and develop a bit of a reason behind this, but what do y'all think?

 

[FrogReaver]

Why were you a pirate? That’s your answer.

 

[77IM]

Pirate and sailor are identical except for the background feature. So if you never once used the background feature in play, then you weren't actually a pirate; that was just you bragging! You were really a sailor all along. You went so far as to write "pirate" on your character sheet, because that's how dedicated you are to role-playing the deception. Imagine everyone's surprise when the Dread Pirate Rupert turns out to be a big softy!

 

[Cap'n Kobold]

The practical effect of the Pirate background is getting away with minor crimes. Perhaps people allow you that because you have a good reputation rather than a bad one?
You're a bit of a celebrity or hero, and so people will turn a blind eye to you plucking an apple off their stall as you swagger by, or bringing their pint, or entering their bar via the window rather than the door.

 

[Allistar1801]

or entering their bar via the window rather than the door.

You give me great Ideas. In all seriousness though, I think the switch up could work between good/bad reputation, I guess the jarring part would just have been me sailing with the pirates. Meh, gotta get to the isle somehow I guess, so why not sail in style by becoming a """ally""" with the pirates and ditching them at the first opportunity

 

[MarkB]

Depending upon the campaign setting, your pirate may have been more of a privateer - part of an independent crew attacking one faction on behalf of another. To the target faction you're a pirate, but to others you may have been fighting for a noble cause.