Advice on an anti-hero

[xyianth]

I’ve been asked to join a game by a friend of mine as a sort of anti-hero. I don’t know much about the campaign world or the party composition. All I know is that my character should provide plenty of potential plot hooks for the DM to use. Since I am usually the DM for my table, this is a rare opportunity for me to be a player.




race: human(variant)
stats(if using point buy): 14(15) str, 10 dex, 14 con, 8 int, 10 wis, 15(16) cha
if rolling: 15+ str, cha>con>dex,wis>int after mods
background: sailor(pirate)
skills: athletics, perception, intimidation, persuasion, deception
tools: navigator’s tools, vehicles(water)
languages: common, infernal(or some other esoteric, vaguely evil, campaign appropriate language)
ECL class details
1 paladin 1 polearm master, divine sense, lay on hands
2 warlock 1 fiend patron, dark one’s blessing, cantrips(eldritch blast, minor illusion), spells(hex, armor of agathys)
3 warlock 2 agonizing blast, devil’s sight, spells(command)
4 warlock 3 pact of the tome(shillelagh, vicious mockery, guidance), spells(darkness, command->blindness/deafness)
5 warlock 4 +2 cha, cantrips(friends), spells(misty step)
6 warlock 5 book of ancient secrets(find familiar, alarm), spells(fireball or hypnotic pattern)
7 paladin 2 divine smite, dueling fighting style
8 paladin 3 divine health, oathbreaker, channel divinity(control undead, dread aspect)
9 paladin 4 warcaster
10 paladin 5 extra attack
11 paladin 6 aura of protection
12 paladin 7 aura of hate
13 paladin 8 +2 cha
14 paladin 9
15 paladin 10 aura of courage
16 paladin 11 improved divine smite
17 paladin 12 lucky
18 fighter 1 second wind, defense fighting style
19 fighter 2 action surge
20 fighter 3 battlemaster archetype, combat superiority(menacing attack, riposte, trip attack)

My backstory: (rough outline)
I sailed the world as a pirate.
I came across an interesting trinket. (probably by theft from true owner)
The trinket linked me to a powerful fiend.
My ship was attacked and sank, but I survived because of unnaturally lucky instincts. (drawn from link to fiend patron)
I am empowered by my patron.
Fiend patron has plans for me, but I don’t know what they are.

Character personality, motivations, and goals:
I am neutral evil. (as in self serving, not as in over the top villain)
I do not shun helping others if it will also help myself.
My pirate reputation comes from the tattooed markings that indicate I was a member of a specific pirate group. The informed can identify the troupe, the uninformed just know that the tattoo is associated with dangerous people.
I’m indebted to the fiend, though I don’t know for sure that it is one. All I know is that it saved my life and gives me power. I’m sure there will eventually be a price, but I don’t currently care.
I am still trying to carve out a life of luxury for myself.
I generally believe that might makes right and ends justify means.
I figure the unknown fiend’s identity and plans provide a decent plot hook. The pirate background with identifiable markings is another plot hook. The theft of the trinket could provide yet another plot hook. The selfish, but willing to help others personality should help move plot lines in interesting directions. And the character is, mechanically, a pretty versatile party asset: high melee damage output, good-to-great defense, utility casting, party face abilities, and a decent ranged attack.

Any suggestions for improvement? or critiques of the concept? Have any ideas for more plot hooks?

[Phion]

I find your build slightly odd for a pirate and personally would have went straight up Rogue (or at least one level into rogue for skill expertise and so on) as I did for my character captain Leeroy Jenkins, I find the skill set is perfect for an anti hero and was easy to become a lovable scum bag.

However being an anti hero isn't about build at the end of the day it is about how you play, you don't have to be dark and brooding (although there's no reason why you can't be either). My advice is find a few flaws in your characters personality (Leeroy has a weakness for gold (which can drop the group in dangerous situations while at the same time can be an advantage)+ adrenaline junky (will attempt crazy feats of skill or gambits) + a coward (this can seem contradictory to the previous assessments but applicable i.e. he once ran into a room and ran out screaming because of giant spiders). Written down that can possibly sound annoying for other players but you have to balance it all out to become memorable yet not overpowering by allowing others to have their chance.

[BladedWizard]

I kind of agree with Phion regarding the built. But yet again... it all depends at which level you start the campaign. As for the pirate background one would assume that you have at least one level of fighter, rogue, or maybe bard. But a background is to simply add flavor to your character. The way I would explain my pirate background and build is as the following:

You were a good paladin (1st level) who found a trinket that forever changed you... you became obsess with the trinket as you felt power within it... that led you to fall into darkness... which granted you your first level of warlock. Then the fiend manipulated you to join a group of pirate for a certain purpose that is unknown to you. Yet you are not even aware that you were manipulated to do so. With time... you grew in power (paladin and warlock)... as a pirate you often tried to conceal your true power and relied on strength alone... which granted you more level of paladin.

Yes it is cliché...

It all depend if the DM wants to build his game around you being a pirate... or if it was something of the past.
Personally I would play an evil bard/rogue or bard/lock. I'm not about power build. I prefer RP and flavor as I find it boring when you have the ultimate build that can do everything. To me it's not real. A bard/lock could fit your pirate background. You joined a pirate group for the adventure and the tales and knowledge of the sea. The trinket... let you to your warlock power. If you want melee... go with the valor bard. I imagine my evil bard who plays eerie type of music... he scare people with his death metal... played on a lute. :P

My two cents... and sorry for my English. It's my second language.

[eastmabl]

I find your build slightly odd for a pirate and personally would have went straight up Rogue (or at least one level into rogue for skill expertise and so on) as I did for my character captain Leeroy Jenkins, I find the skill set is perfect for an anti hero and was easy to become a lovable scum bag.

Dread Paladin Roberts
Annoying do-gooder (ADG) with paladin levels sets sail on a ship for his one true love. The ship is attacked by the original Dread Paladin Roberts (oDPR). With ADG the sole survivor, oDPR sees the love in his heart and offers him the chance to study under him and become the new Dread Paladin Roberts (nDPR). Through a timely conversion to 5e, ADG ditches his lawful stupid ways and heeds common sense!

ADG sails with oDPR becoming his first mate and learning under him (Sailor background). At some point, the ship goes to port and oDPR retires, granting the ship and a shiny trinket to ADG-now-nDPR. The shiny trinket speaks to him and promises him power beyond imagine if he serves the entity that created the trinket. The New Dread Paladin Roberts agrees to serve to this bargain because it conveniently does not offend his Dread Paladin oath, and suddenly he is infused with fell power from Entity-ville! He gets back on his boat and sails away, wreaking havoc on shipping until the impending nuptuals of the one true love entails that he leave his piratical ways and save her!

Paladin 2/Warlock 1, Sailor background. It might entail that his bond is to the one true love. It's an interesting way to build it - especially if you don't announce your character concept to the rest of the group but let them figure it out on their own.

However you wish. Fred Savage not included.

[Phion]

Dread Paladin Roberts
Annoying do-gooder (ADG) with paladin levels sets sail on a ship for his one true love. The ship is attacked by the original Dread Paladin Roberts (oDPR). With ADG the sole survivor, oDPR sees the love in his heart and offers him the chance to study under him and become the new Dread Paladin Roberts (nDPR). Through a timely conversion to 5e, ADG ditches his lawful stupid ways and heeds common sense!

ADG sails with oDPR becoming his first mate and learning under him (Sailor background). At some point, the ship goes to port and oDPR retires, granting the ship and a shiny trinket to ADG-now-nDPR. The shiny trinket speaks to him and promises him power beyond imagine if he serves the entity that created the trinket. The New Dread Paladin Roberts agrees to serve to this bargain because it conveniently does not offend his Dread Paladin oath, and suddenly he is infused with fell power from Entity-ville! He gets back on his boat and sails away, wreaking havoc on shipping until the impending nuptuals of the one true love entails that he leave his piratical ways and save her!

Paladin 2/Warlock 1, Sailor background. It might entail that his bond is to the one true love. It's an interesting way to build it - especially if you don't announce your character concept to the rest of the group but let them figure it out on their own.

However you wish. Fred Savage not included.

Oh no background is completely possible as you pointed out it's just at a stretch also I am thinking further down the line a character more along the lines of a rouge has the skill set to become a memorable anti-hero. To be fair this is simply my preference in style, I love rouge thief and often use cheap tactics such as pulling down the enemies helmet over their eyes or throwing my jacket at them gaining temporary advantage via blinding them thus sneak attack. Really anyone can be classed as an anti hero since it is based on that characters actions I just view the rogue as that class that captures the vibe so well; fighting dirty and perhaps for selfish reasons yet possibly a reason for why they behave how they do and perhaps deep down a noble side.