Charlatan-turned-Knight: Class Suggestion!

[Ninjadeadbeard]

I have a fun idea for a character and I'd like some class suggestions. He's basically a con artist and scammer who got saved from a mob and picked off the street by a wandering knight errant, and decided to follow around this schmuck until he could make a big score. Low and behold, as time passed, he grew to genuinely like the knight, and sort of became his squire. Still an opportunistic git, but one that only stole from those that could afford it (and sometimes ended up giving it away to those who needed it).

Anyway, knight eventually goes down to a poison arrow meant for my character or something suitably self-sacrificing, and the charlatan decided to take up the knight's cause: accumulate enough wealth and title to win the hand of his childhood sweetheart. Since the knight himself is kill, and the charlatan can reasonably pass for him (at least in broad dimensions), the charlatan has taken up the knight's weapons (had the longsword lightened to count as a rapier), armor, and even his name in an attempt to finish the quest, by any means necessary.

I'm torn between two options, though I'll take any suggestions. Swashbuckler with a level or two dip in Fighter for armor (gotta get that chainmail knight look), or a War Bard, which gets me armor, but also spellcasting. Spellcasting's nice, but it doesn't 100% mesh with the character concept. I'll take it, of course, but it's not a huge priority because my DM doesn't force us to optimize or anything. I just want to get the most fun build out of this concept.

tl;dr I'm a charlatan thief pretending to be a knight. What is a fun-but-effective build to simulate that?

[Aett_Thorn]

Well, since you'll probably have good Str, Con, and Charisma, a Paladin of some sort would be an ideal fit from a mechanical perspective.

However, a Cavalier/Swashbuckler combo would be an interesting, if tough, fit. You'd just need to make sure that you have at least a 13 Dex as well.

[The_Jette]

I second the vote for Paladin. Seems the obvious choice, though. And, I am loathe to admit the obvious choice might be the best...

[Temperjoke]

I don't know that I would go with paladin, necessarily; I mean, mechanically, sure it works, but the Oaths would be the issue. The character wants to take up the Knight's quest, but that's not avenging him, and that would be the closest Oath to the circumstances. Depending on what level you're starting at, I'd start with Swashbuckler Rogue, then start moving into Cavalier Fighter to signify the new path he's taking. Stat-wise, since you want chainmail armor, you'll need a minimum of 13 in STR, but otherwise I'd put the emphasis on DEX and CON.

[Afrodactyl]

Cavalier fighter/thief rogue?

[Nidgit]

This screams fighter/rogue multiclass to me. Pick whichever non-magical fighter subclass you want to compliment Arcane Trickster, Swashbuckler, or Thief and go for a 5/15 or 8/12 split.

[smcmike]

I think it really depends on your vision for the character. There are lots of mixes that could work, really.

To me, it sounds like this guy is primarily a grifter - a charisma specialist, rather than a dexterity-based sneak. Obviously there’s some support for that with swashbuckler, but I’d probably go Bard, then add on some paladin for his change of heart.

[Zanthy1]

If I were making this character, I would probably go thief and cavalier. Thief to get those fast hands and extra movement, which could surprise other knights you may come across (How does he move so fast!), and Cavalier seems like the most knightly fighter subtype. Plus this way you don't have any magic, ut plenty of cool abilities and your own code of honor

[GlenSmash!]

Isn't Charlatan already a background? Why not just take that background and be a Cavalier/Banneret/Battlemaster/Champion/ or paladin?