Player wants a gangster

[EggKookoo]

I'm getting ready to start my big new 5e session soon. I have players running a druid, sorc, monk (shadow), and paladin. Then I invited another player in who loves rogues. I told him the monk player is already planning to go the stealth/recon route, and he's okay with that. He's thinking of taking his rogue more down the assassination/combat route, and suggested that he play out more like a member (or perhaps former member) of a criminal organization. That's cool, he wants a gangster and will probably go with the criminal background. But...

Well, the assassin archetype is really kinda weak. I mean, Assassinate is cool, but then it just kind of trails off.

So what could I suggest to him? I'd consider having him multiclass fighter/rogue but he really likes Sneak Attack and will probably want to maximize it. It might be a hard sell to dilute rogue levels. I might be able to sell him on getting enough levels to gain Extra Attack.

I've also been thinking of going with the revised ranger hunter and having him pick humanoids for Favored Enemy. That would allow him to dish out damage pretty highly against "people" enemies which fits him being a gangster, but it also comes with some spellcasting and he's decidedly anti-spellcaster (too much bookkeeping). And I'd have to sell him on losing SA but I might be able to just run the numbers; RR/hunter is pretty vicious.

Any thoughts on this? How would you model an agility/mobility-based martial character without using a monk?

[nickl_2000]

Mastermind and go the route of Kingpin?

[Unoriginal]

Mastermind and go the route of Kingpin?

This. Mastermind's made for it.

[EggKookoo]

Oh, I didn't even think to look in Xanathar's. Thanks!

[JackPhoenix]

Maximizing sneak attack? Swashbuckler. No need to have advantage or friends around to get SA, and he can use his BA for TWF and still retreat without provoking OA.

[Mr.Spastic]

Are you building his character because he is new or because he wants you too?

If he wants you build it for him to than Mastermind for a Kingpin type, Swashbuckler for your typical dervish rogue(they make great melee rogues though), Thief doesn't have a lot of combat power but will be better at pickpocketing, Arcane Trickster is a thing I guess, Scout is kinda woodsy, and Inquisitor is more like a private detective. Over all though, most rogue subclasses don't provide a lot of combat prowess.

If he is new to the game or doesn't fully understand the rules you should talk with him and explain what each subclass does and let him pick for himself.

[Man_Over_Game]

I'm sorry, but I'd recommend scratching the Mastermind off. It's a good option for a social character, but it definitely lacks in combat. But there's a better solution for the same playstyle that isn't Assassin OR Stealth and is great as a hitman:

The Battle Master.

Hear me out. Battle Master Fighter starts with 4 maneuvers, each that can be used in melee combat AND ranged combat, using Dexterity OR Strength, and they're allowed to use medium armor. Also, almost every one of their maneuvers doesn't touch their Bonus Action, and besides the once-per-short-rest Second Wind, the Fighter won't have much that uses their Bonus Action, which ties directly into the Rogue.

Rogue 2, Battle Master Fighter X. Use ranged attacks to knock your enemies prone at long range (cuts their speed in half, means more ranged attacks), use Feint Attack to get advantage on your own attacks to proc Sneak Attack at range. Then, when they are stupid enough to engage you in melee combat, you put away the bow and swap to your twin swords and mop up. Or screw the swords and grab Sharpshooter + Crossbow Expert and go to town, since your hand crossbow with Xbow Xpert will allow it to serve as a melee weapon, getting +2 damage from Archery.

Take Stealth as a skill, but put your Expertise into Athletics and Thieves' Tools.

You're called The Professional.

[Digimike]

Assassin Rogue and Oath of Vengeance Paladin actually work amazingly well together. You lose out on some Sneak attack dice, but you gain a bigger hit die, smite, you can provide your own advantage, and extra movement against people escaping. Also some cool tricks like misty step and haste. Plus you end up with more attacks per round.

Smite Damage can also benefit from crits just like sneak attack dice, so the auto crit blends well for one hell of an opening round.

Sure paladin doesn't sound very thuggish, but its not like paladin is LG anymore. And the benefits of this multiclass should sell the player on it.

[EggKookoo]

Maximizing sneak attack? Swashbuckler. No need to have advantage or friends around to get SA, and he can use his BA for TWF and still retreat without provoking OA.

Yeah, the more I look at it, the more Swashbuckler seems to fit.


Are you building his character because he is new or because he wants you too?

I'm not going to actually build out the character. He's not at all new to D&D but he's not very experienced with 5e. I did have a high-level game he played in (with a rogue, of course) so he gets the idea. I don't know if he really knows all his options.


If he is new to the game or doesn't fully understand the rules you should talk with him and explain what each subclass does and let him pick for himself.

He's building it all. My job is to make sure he's aware of what builds fit his concept, and to what degree they deviate. In the end he could just go with a thief or something. Which is fine, it's his character and he should build what's fun for him.

[JakOfAllTirades]

Wow, tons of interesting ideas in this thread I hadn't thought of before. This is why I read this forum!

[Brother carc]

Personally I think arcane trickster aiming for shadow blade and later haste gives you the best sneak attack progression.

Lvl. 1-3 booming blade then disengage to make the opponent trigger the effect. Use an owl familiar to give you advantage.
Level 4. Take elven accuracy for increased advantage
Level 5. Booming blade damage goes up
Level 7. Take shadow blade and combo with booming blade for extra damage/other source of advantage
Level 11. Booming blade damage goes up again
Level 13. Shadow blade damage goes up and/or use haste to trigger two sneak attacks a round. Can also use mage hand for advantage

Combined with sneak attack dice it gives you solid damage potential, possible synergy with elven accuracy and still all the usual arcane trickster shenanigans

[jdolch]

I second the BM Fighter/Rogue Route.

[Contrast]

Well, the assassin archetype is really kinda weak. I mean, Assassinate is cool, but then it just kind of trails off.


I actually really like the other assassin abilities though you're correct that they do not make the PC better in combat directly.

If he's considering more of a thug you might actually want to consider a barbarian dip and make a strength based rogue. You still have to use a finesse weapon but you don't actually have to use Dex, you can still use strength if you want. Reckless attach to generate advantage, then disengage to avoid them being able to hit you back. Works particularly well as a mountain dwarf.

Expertise in athletics and shield master is also a fun option. Worse if you follow the current guidance on how shield master works of course, and it does take your bonus action so possibly better if you're planning more barb levels than you are rogue.

[Kefvin]

I'm getting ready to start my big new 5e session soon. I have players running a druid, sorc, monk (shadow), and paladin. Then I invited another player in who loves rogues. I told him the monk player is already planning to go the stealth/recon route, and he's okay with that. He's thinking of taking his rogue more down the assassination/combat route, and suggested that he play out more like a member (or perhaps former member) of a criminal organization. That's cool, he wants a gangster and will probably go with the criminal background. But...

Well, the assassin archetype is really kinda weak. I mean, Assassinate is cool, but then it just kind of trails off.

So what could I suggest to him? I'd consider having him multiclass fighter/rogue but he really likes Sneak Attack and will probably want to maximize it. It might be a hard sell to dilute rogue levels. I might be able to sell him on getting enough levels to gain Extra Attack.

I've also been thinking of going with the revised ranger hunter and having him pick humanoids for Favored Enemy. That would allow him to dish out damage pretty highly against "people" enemies which fits him being a gangster, but it also comes with some spellcasting and he's decidedly anti-spellcaster (too much bookkeeping). And I'd have to sell him on losing SA but I might be able to just run the numbers; RR/hunter is pretty vicious.

Any thoughts on this? How would you model an agility/mobility-based martial character without using a monk?





Im playing a Battlebuckler Swashbuckler/Battlemaster, currently at 3/5

Im enjoying it immensly. Started off with rouge for expertise and as soon as I hit lvl 3 I went fighter all the way to 5 for the extra attack. My charname really shines in combat, dodgeing in and out of combat without provoking OA. Duelling with bosses while using his riposte manouver to dish out two sneak attacks, one in my round and one if the enemy misses. He is also a bit of a gangster in his spare time, he has a gambling addiciton so he frequently pockets loot found in the dungeon to fund this. He also intimidates and threatens people in the gambling halls etc etc while in town.

[CTurbo]

Im playing a Battlebuckler Swashbuckler/Battlemaster, currently at 3/5

Im enjoying it immensly. Started off with rouge for expertise and as soon as I hit lvl 3 I went fighter all the way to 5 for the extra attack. My charname really shines in combat, dodgeing in and out of combat without provoking OA. Duelling with bosses while using his riposte manouver to dish out two sneak attacks, one in my round and one if the enemy misses. He is also a bit of a gangster in his spare time, he has a gambling addiciton so he frequently pockets loot found in the dungeon to fund this. He also intimidates and threatens people in the gambling halls etc etc while in town.

This^^^^


This is pretty much what I was gonna say. Swashbuckler is perfect for what he's looking for and Battlemaster only makes it better. Take Sentinel at some point along with Riposte and you'll use sneak attack twice per round all the time.

I'd take at least Rogue 3 before dipping Fighter at which point I'd probably just go 5 straight levels before going back to Rogue and staying. If you want to TWF you could stick to just 3 levels of Fighter. Defense, TWF, or Dueling would be great depending on what style he had in mind.

[Trustypeaches]

Just play a Barbarian / Rogue Strength Rogue.

The classes have a lot of unexpected synergy. You activates Sneak attack with Reckless Attack and knock fools over with Expertise athletics checks. Medium armor and shield proficiency. If you use a rapier, you benefit from both Sneak attack and Rage (you can reflavor it to another weapon if you want).

I think that captures a “beat em up” thug.

[EggKookoo]

All these suggestions are great, thanks everyone!

I'm going to suggest swashbuckler first, and suggest variant human and Sentinel (or Alert or Lucky) as the first feat. If that's a no-go we'll work it out from there. Maybe see if he's interested in the revised ranger hunter for the sheer humanoid damage. Not the same flavor as SA but it might do.

The pally is already planning to go vengeance so I don't want to dilute that. And I leave multiclassing as a last resort. I won't stop him from doing that but I feel like that's something for someone who has considerable system experience and is willing to take on the extra complexity.

[Vogie]

I'd throw in an Inquisitive rogue

When I think of Gangster, I don't think of a thuggish one-on-one enforcer or duelist like a Swashbuckler would be. I think instead of a character who is always on the lookout for something odd, disruptions in their business. They'd be quiet, watchful, sphinx-like. Power as in business suit, rather than power as in plate armor.

If the player also wants their character to be able to fight dirty, mix in the Martial Adept feat and/or some levels of battlemaster fighter.

[CTurbo]

Single class Swashbuckler would work just fine. Just make it tougher than a normal Swashbuckler would be. Vhuman with Moderately Armored feat at level 1 and you could start with 16 Dex, 16 Con, and 14 Cha. Breast plate + Shield would be 18 AC. As soon as you bump Dex to 18, Studded Leather + Shield would also be 18 AC.

[KorvinStarmast]

Im playing a Battlebuckler Swashbuckler/Battlemaster, currently at 3/5

Im enjoying it immensly. Started off with rouge for expertise and as soon as I hit lvl 3 I went fighter all the way to 5 for the extra attack. My charname really shines in combat, dodgeing in and out of combat without provoking OA. Duelling with bosses while using his riposte manouver to dish out two sneak attacks, one in my round and one if the enemy misses. He is also a bit of a gangster in his spare time, he has a gambling addiciton so he frequently pockets loot found in the dungeon to fund this. He also intimidates and threatens people in the gambling halls etc etc while in town. *golf clap* if we start a new campaign next year, this looks like a for sure character concept for at least two of the people i our group.