UPDATED: The Drow Pirate Roberts Monk/Swashbuckler Multi-Class Concept

[DrowPiratRobrts]

Hey all! I'm looking for input on how to optimize my character, The Drow Pirate Roberts. He's an eccentric Drow who fled the oppressive drow society in search of a free life on the surface world. Long story short, he's a heavy drinker who seeks adventure and wants to be captain of a sky ship some day. In RP situations he's boisterous and a bit of a show-off. On the battlefield he's a loose-cannon, unpredictable, dangerous,etc. You never know what he's going to do with his suave gentlemanly way...did I mention he's a gentleman pirate??? This makes for some of my favorite RP I've ever done. I really want to know if anyone sees any glaring weaknesses/fall-off points in my build before I commit to it tomorrow. Onto the logistics:

I'm a Monk, but I'm thinking about splitting into an assassin as well. If I did, I would likely go Way of the Shadow Monk lvl 11/Assassin Rogue lvl 9. This seems optimal to me, but I could be overlooking something. It seems that I get the most out of each archetype as I pick up Infiltration Expertise at level 9 assassin and Cloak of Shadows at Monk 11...Cloak of Shadows is dope af for a pirate drow assassin loose cannon. Basically, I'm drawing inspiration from Jack Sparrow, One Piece, and Drizzt. Any thoughts on optimization are more than welcome! Here's my character info at level 3 (I'm about to lvl into monk 4 or rogue 1):

Str: 14
Dex: 20
Con: 15
Int: 11
Wis: 17
Cha: 14

Note: My DM will allow Sneak Attack Dice on attacks made with any monk weapons and/or unarmed strikes. So at level 5 I could attack twice with sneak attack (plus two unarmed strikes from flurry of blows). My DM thinks it's crazy but wants to allow it because of the uniqueness of my character. #successfulRPissuccessful

[Biggstick]

Hey all! I'm looking for input on how to optimize my character, The Drow Pirate Roberts. He's an eccentric Drow who fled the oppressive drow society in search of a free life on the surface world. Long story short, he's a heavy drinker who seeks adventure and wants to be captain of a sky ship some day. In RP situations he's boisterous and a bit of a show-off. On the battlefield he's a loose-cannon, unpredictable, dangerous,etc. You never know what he's going to do with his suave gentlemanly way...did I mention he's a gentleman pirate??? This makes for some of my favorite RP I've ever done. I really want to know if anyone sees any glaring weaknesses/fall-off points in my build before I commit to it tomorrow. Onto the logistics:

I'm a Monk, but I'm thinking about splitting into an assassin as well. If I did, I would likely go Way of the Shadow Monk lvl 11/Assassin Rogue lvl 9. This seems optimal to me, but I could be overlooking something. It seems that I get the most out of each archetype as I pick up Infiltration Expertise at level 9 assassin and Cloak of Shadows at Monk 11...Cloak of Shadows is dope af for a pirate drow assassin loose cannon. Basically, I'm drawing inspiration from Jack Sparrow, One Piece, and Drizzt. Any thoughts on optimization are more than welcome! Here's my character info at level 3 (I'm about to lvl into monk 4 or rogue 1):

Str: 14
Dex: 20
Con: 15
Int: 11
Wis: 17
Cha: 14

Note: My DM will allow Sneak Attack Dice on attacks made with any monk weapons and/or unarmed strikes. So at level 5 I could attack twice with sneak attack (plus two unarmed strikes from flurry of blows). My DM thinks it's crazy but wants to allow it because of the uniqueness of my character. #successfulRPissuccessful

Does the DM you're playing with allow SCAG? You might find the Swashbuckler arch type as rather fitting for your suave show off of a pirate captain. Adding Charisma to your initiative, never needing an ally next to an enemy to gain your sneak attack damage (melee only), and having the mobility feat built in, all online at level 3? That sounds like a much better fit then the Assassin route imo.

The other thing I'd bring up is the level 9 ability you're talking about within rogue. Infiltration Expertise sounds nice and everything, but you're still a Drow. I'm not sure how big the world is or how welcoming it is of Drow, but most societies aren't really big fans of Drow. While RAW the book says you should be able to create these identities, I think the DM will probably rule something along the lines of being suspicious of you simply for being a Drow, no matter how good your created identity is. Of course this entire assumption is based on Drow being looked down upon in your DM's world.

Lastly, picking up level 7 in both classes is wasted since evasion from both classes doesn't stack. I personally really like Shadow Monk 6 / Swashbuckler 14. (You can change the rogue arch type to whatever your preference is, I just really enjoy the benefits of Swashbuckler).

[DrowPiratRobrts]

Does the DM you're playing with allow SCAG? You might find the Swashbuckler arch type as rather fitting for your suave show off of a pirate captain. Adding Charisma to your initiative, never needing an ally next to an enemy to gain your sneak attack damage (melee only), and having the mobility feat built in, all online at level 3? That sounds like a much better fit then the Assassin route imo.

The other thing I'd bring up is the level 9 ability you're talking about within rogue. Infiltration Expertise sounds nice and everything, but you're still a Drow. I'm not sure how big the world is or how welcoming it is of Drow, but most societies aren't really big fans of Drow. While RAW the book says you should be able to create these identities, I think the DM will probably rule something along the lines of being suspicious of you simply for being a Drow, no matter how good your created identity is. Of course this entire assumption is based on Drow being looked down upon in your DM's world.

Lastly, picking up level 7 in both classes is wasted since evasion from both classes doesn't stack. I personally really like Shadow Monk 6 / Swashbuckler 14. (You can change the rogue arch type to whatever your preference is, I just really enjoy the benefits of Swashbuckler).

I'll definitely look into that! I'm waiting on a response about using SCAG and the Swashbuckler. Is that a rogue archetype or an individual class? I also asked about feelings toward Drow since I'm jumping in at level 3 and don't really know the world. We'll see how it goes. I will check out the Swashbuckler once I find access to the SCAG.

[Biggstick]

I'll definitely look into that! I'm waiting on a response about using SCAG and the Swashbuckler. Is that a rogue archetype or an individual class? I also asked about feelings toward Drow since I'm jumping in at level 3 and don't really know the world. We'll see how it goes. I will check out the Swashbuckler once I find access to the SCAG.

Swashbuckler is a rogue archetype. Reading your description of the character, it definitely seems to fit the Swashbuckler attitude and style in combat.

[DrowPiratRobrts]

Lastly, picking up level 7 in both classes is wasted since evasion from both classes doesn't stack. I personally really like Shadow Monk 6 / Swashbuckler 14. (You can change the rogue arch type to whatever your preference is, I just really enjoy the benefits of Swashbuckler).


Here's my thought on the level breakdown. I'm going to do Swashbuckler/Shadow Monk. I'm currently a Level 3 Shadow Monk and a Level 1 Rogue. The reason I was thinking 11Mo/9Rg is because of the increasing Martial Arts Die finishing at 1d8 and the Sneak Attack Die at 5d6. The double dip Evasion doesn't bother me since even though I only get 4 ASIs my stats are already pretty great, and I won't need to spread the points out beyond WIS, CON, and maybe CHA.

So I would gain 2d6 Sneak Attack and Reliable Talent as quite possibly the best bonus of a Lvl 14 Swashbuckler and a proficiency bonus of +5 as opposed to +4 (not bad). Elegant Maneuver won't be a huge benefit IMO since my acrobatics with expertise is already at +9 at 4th lvl.

On the other hand, I lose 5 ki points (huge loss since flurry of blows counts for sneak attack trigger with my DM) and 5 ft speed (synergizes well with Swashbuckler). I also drop from a d8 to a d6 for my Martial Arts die. Remember, if I use flurry of blows at level 11 I'll be making 4 attacks per turn with a d8+5 and my sneak attack dice on first hit(dependent on Rogue lvl). I also lose Unarmored Movement Improvement (great for RP or Combat) and Cloak of Shadows which drastically improves the usefulness/utility from Shadow Step.

Thanks for the Swashbuckler suggestion. I didn't even know it existed! It's way better for my character than Assassin. What do you think about only doing 9 levels though and putting the rest into monk? I hope that explanation makes half sense at least.

[RaynorReynolds]

Hey all! I'm looking for input on how to optimize my character, The Drow Pirate Roberts. He's an eccentric Drow who fled the oppressive drow society in search of a free life on the surface world. Long story short, he's a heavy drinker who seeks adventure and wants to be captain of a sky ship some day. In RP situations he's boisterous and a bit of a show-off. On the battlefield he's a loose-cannon, unpredictable, dangerous,etc. You never know what he's going to do with his suave gentlemanly way...did I mention he's a gentleman pirate??? This makes for some of my favorite RP I've ever done. I really want to know if anyone sees any glaring weaknesses/fall-off points in my build before I commit to it tomorrow. Onto the logistics:

I'm a Monk, but I'm thinking about splitting into an assassin as well. If I did, I would likely go Way of the Shadow Monk lvl 11/Assassin Rogue lvl 9. This seems optimal to me, but I could be overlooking something. It seems that I get the most out of each archetype as I pick up Infiltration Expertise at level 9 assassin and Cloak of Shadows at Monk 11...Cloak of Shadows is dope af for a pirate drow assassin loose cannon. Basically, I'm drawing inspiration from Jack Sparrow, One Piece, and Drizzt. Any thoughts on optimization are more than welcome! Here's my character info at level 3 (I'm about to lvl into monk 4 or rogue 1):

Str: 14
Dex: 20
Con: 15
Int: 11
Wis: 17
Cha: 14

Note: My DM will allow Sneak Attack Dice on attacks made with any monk weapons and/or unarmed strikes. So at level 5 I could attack twice with sneak attack (plus two unarmed strikes from flurry of blows). My DM thinks it's crazy but wants to allow it because of the uniqueness of my character. #successfulRPissuccessful

Keep in mind sneak attack is only once per round.

[DrowPiratRobrts]

Keep in mind sneak attack is only once per round.

Yep! It's actually once per turn though which means it can be triggered by OAs.

[RickAllison]

Yep! It's actually once per turn though which means it can be triggered by OAs.

Indeed, but rogues are pretty awful at taking advantage of OAs. As someone who has done the Swashbuckler, going up to 9 with that would be a blast! At that point, you get Panache, which lets you make a Persuasion check to penalize the creature for attacking anyone but you, and you would still have the bonus action to teleport around and the heightened movement to mess with your foes while slinging quips.

[Biggstick]

Thanks for the Swashbuckler suggestion. I didn't even know it existed! It's way better for my character than Assassin. What do you think about only doing 9 levels though and putting the rest into monk? I hope that explanation makes half sense at least.

If you're more focused on picking up the Monk levels, or at least primarily being a Monk, I wouldn't advise going past level 5 Rogue. Reasoning behind this is levels 6-9 are levels that don't really bring much to the character's power. The only things you're gaining for 4 levels of Rogue aren't as valuable as the things you'd gain from the 4 levels of Monk


Rogue levels 6-9 features: Expertise in 2 skills, Evasion (already have from Monk), an ASI (equal with Monk), your Roguish archetype feature (which as a Swashbuckler isn't big enough imo to warrant 4 levels), and an additional 2d6 to your 3d6's of sneak attack damage (total of 5d6 as compared to 3d6).

Monk levels 12-15 features: an ASI (equal with Rogue), Tongue of the Sun and Moon (You understand everyone and everyone understands you), Diamond Soul (proficiency in all saving throws, and the ability to burn a Ki point to re-roll a failed save), Timeless Body (flavor, but not having to eat or drink while at sea is pretty cool), 4 Ki points, and 5' of movement.


I'm not sure how you view the value of each thing, but I personally really like proficiency in all saving throws and being able to speak/understand all languages. I think the language thing would be interesting as well with your character. You can show off your gentlemanly swagger to even that insert whatever terrible monster here and both parties will understand each other.

[RickAllison]

If you're more focused on picking up the Monk levels, or at least primarily being a Monk, I wouldn't advise going past level 5 Rogue. Reasoning behind this is levels 6-9 are levels that don't really bring much to the character's power. The only things you're gaining for 4 levels of Rogue aren't as valuable as the things you'd gain from the 4 levels of Monk


Rogue levels 6-9 features: Expertise in 2 skills, Evasion (already have from Monk), an ASI (equal with Monk), your Roguish archetype feature (which as a Swashbuckler isn't big enough imo to warrant 4 levels), and an additional 2d6 to your 3d6's of sneak attack damage (total of 5d6 as compared to 3d6).

Monk levels 12-15 features: an ASI (equal with Rogue), Tongue of the Sun and Moon (You understand everyone and everyone understands you), Diamond Soul (proficiency in all saving throws, and the ability to burn a Ki point to re-roll a failed save), Timeless Body (flavor, but not having to eat or drink while at sea is pretty cool), 4 Ki points, and 5' of movement.


I'm not sure how you view the value of each thing, but I personally really like proficiency in all saving throws and being able to speak/understand all languages. I think the language thing would be interesting as well with your character. You can show off your gentlemanly swagger to even that insert whatever terrible monster here and both parties will understand each other.

Unfortunately, the loss of Tongue of the Sun and Moon is pretty big for the Swashbuckler. With it, he can taunt and use the Panache feature (which can actually be really powerful if you have a high Charisma) on any creatures who understand a language. Makes for a fun idea for a gestalt campaign, however!

[DrowPiratRobrts]

If you're more focused on picking up the Monk levels, or at least primarily being a Monk, I wouldn't advise going past level 5 Rogue. Reasoning behind this is levels 6-9 are levels that don't really bring much to the character's power. The only things you're gaining for 4 levels of Rogue aren't as valuable as the things you'd gain from the 4 levels of Monk


Rogue levels 6-9 features: Expertise in 2 skills, Evasion (already have from Monk), an ASI (equal with Monk), your Roguish archetype feature (which as a Swashbuckler isn't big enough imo to warrant 4 levels), and an additional 2d6 to your 3d6's of sneak attack damage (total of 5d6 as compared to 3d6).

Monk levels 12-15 features: an ASI (equal with Rogue), Tongue of the Sun and Moon (You understand everyone and everyone understands you), Diamond Soul (proficiency in all saving throws, and the ability to burn a Ki point to re-roll a failed save), Timeless Body (flavor, but not having to eat or drink while at sea is pretty cool), 4 Ki points, and 5' of movement.


I'm not sure how you view the value of each thing, but I personally really like proficiency in all saving throws and being able to speak/understand all languages. I think the language thing would be interesting as well with your character. You can show off your gentlemanly swagger to even that insert whatever terrible monster here and both parties will understand each other.

Thank you! I think that's what I'll do! I've wanted to try to get some of the higher levels of monk abilities, but I wasn't certain that it was possible until now. This has been a great help, really! You've explained things very simply and made a great case. I agree with the RP value of Tongue of Sun and Moon and Timeless Body. The other stats pretty much speak for themselves.

[Biggstick]

Unfortunately, the loss of Tongue of the Sun and Moon is pretty big for the Swashbuckler. With it, he can taunt and use the Panache feature (which can actually be really powerful if you have a high Charisma) on any creatures who understand a language. Makes for a fun idea for a gestalt campaign, however!

You would not be able to access both the Panache feature of Swashbuckler and the Tongue of the Sun and Moon on the same PC. Panache comes online at Rogue level 9 and Tongue of Sun and Moon at Monk level 12.

[RickAllison]

You would not be able to access both the Panache feature of Swashbuckler and the Tongue of the Sun and Moon on the same PC. Panache comes online at Rogue level 9 and Tongue of Sun and Moon at Monk level 12.

Indeed, that is literally what I just stated in the post you quoted :smalltongue: Hence why at the end I stated:


Makes for a fun idea for a gestalt campaign, however!

I clearly stated that it would be great for a campaign style in which the PC takes two class progressions. I was lamenting that monks couldn't get the ribbon earlier, as then it would have been a potent combination.

[DrowPiratRobrts]

Thanks everyone for your contributions! If anyone else has input, it's definitely welcome! I'm also interested in anyone who has been inspired by this idea to create some other character. As a side note since I'm a new user, is there a way to change the title of the thread to Swashbuckler instead of Assaasin? Just curious.

[DrowPiratRobrts]

Thanks everyone for your contributions! If anyone else has input, it's definitely welcome! I'm also interested in anyone who has been inspired by this idea to create some other character. As a side note since I'm a new user, is there a way to change the title of the thread to Swashbuckler instead of Assaasin? Just curious.

Yeah, you just edit the original post yah dunce! :P

[Biggstick]

Indeed, that is literally what I just stated in the post you quoted :smalltongue: Hence why at the end I stated:

I clearly stated that it would be great for a campaign style in which the PC takes two class progressions. I was lamenting that monks couldn't get the ribbon earlier, as then it would have been a potent combination.

My apologies. I've never heard the gestalt term before. You would be correct though lol.

[RickAllison]

My apologies. I've never heard the gestalt term before. You would be correct though lol.

It was more of a thing in 3.X, as I understand. I would be very intrigued to try a game with it as there are so many class combinations that wouldn't normally be possible with double the class levels. Completely understandable not to have heard it if you haven't lurked in the right threads :smallsmile:

[PoeticDwarf]

No. Not Roberts. Not him again. Noooooo

Oh wait, this is a drow not an halfling

Glad nobody heard me

I am scared

[DrowPiratRobrts]

No. Not Roberts. Not him again. Noooooo

Oh wait, this is a drow not an halfling

Glad nobody heard me

I am scared

Lol wat????

[RulesJD]

I have a level 9 Shadow Monk/3 Swashbuckler.

Ton of fun to play, but watch your bonus actions, they get really busy between shadowstep, cunning action, and bonus action attack.

[PoeticDwarf]

Lol wat????

Something from a campaign I played with a dreaded vampire parite called Roberts

[Southpaw]

Indeed, but rogues are pretty awful at taking advantage of OAs. .

Well, if the DM is allowing monk weapons to get sneak attack damage try to fit Pole Arm Master in there somewhere. Wack them on the head with your quarterstaff with Sneak attack damage and back up a few feet (no AoO against you thanks to Swashbuckler). Let the opponent close back in with you and get your own AoO due to them entering your threat area with PAM with another dose of Sneak Attack damage. Extra points if you can fit in Booming Blade. I believe I am looking at the this all correctly.