Why have one rogue when you could have two! Working together with some deceptive wit, Double Trouble Rogues don their trenchcoat in social encounters, blending in as members of taller species, just as quickly doffing it in combat to confuse their enemies and add presence to the battlefield. These rogues master the art of teamwork to artfully move, dodge, and attack as one, using their unusual nature as a benefit rather than a hinderance. These rogues tend to members of shorter species such as Goblins, Halflings, or Gnomes, but Double Trouble Rogues may also exist with larger species such as humans provided they are trying to blend in with communities of taller species such as Goliaths or Giants. One might be surprised how many seemingly unassuming members of the community are actually two people in disguise. 

This subclass is a work in progress, and suggestions are welcome!

Credit goes to Zoken44 who created a similar, very popular subclass on which this is based (DnD Beyond won't let me share the link, but the subclass was called "Two Goblins in a Trenchcoat"). This subclass is meant to mechanically refine some of the ideas created by them, and introduce other original ones where I felt they would work better. 

Level 3: Collaboration

You have two forms, a ‘split’ form and a ‘combined’ form. Your ‘combined’ form has your normal statistics and abilities. Your ‘split’ form splits you into two creatures, or halves, with the following properties: 

• Each of these creatures have max health equal to half of your max health in your ‘combined’ form, and begin with current health equal to half of the current health your ‘combined’ form had before you split. 
• These creatures each have speed equal to your walking speed and may each move on your turn. 
• These creatures move on the same initiative, retain all abilities of their ‘combined’ form, and share actions, bonus actions, and reactions. 
• Both of these creatures retain any conditions affecting you when you split from your ‘combined’ form 
• If one of these creatures drops to 0 hp, they will not start making death saving throws until the other half is killed or dropped to 0 hp. Death saving throws are rolled collectively between the two halves rather than individually. Damage equal to twice a half’s max hp does not kill it, but instead drops it to 0 hp.
• Any actions taken as part of the Cunning Action ability apply to both halves

While in ‘split’ form, if both halves are within 5ft of the same creature and aren’t incapacitated, attacks may benefit from sneak attack so long as they are not at disadvantage. Further, while in ‘split’ form, if both halves are within 5ft of each other, they may choose to rejoin as a bonus action. If they do so, they convert to ‘combined form’, with current hp equal to the sum of each of the halves’ current hp. Your ‘combined’ form retains all conditions affecting both halves when it converts. At the end of your turn if you are not in combat and you are in your ‘split’ form, provided at least one half has more than 0 hp, you rejoin into you ‘combined’ form in the space of one of the halves (your choice) if they are physically able to rejoin each other. If they cannot, choose one half to be immobile as if under the stunned condition, except it can speak, until the other half comes within 5ft of them. 

Convincing Ruse

Beginning at 3rd level, you have honed your disguise in order to pull off roguish ruses. While in your ‘combined’ form, you have advantage on Deception and Performance checks to convince others you are one person. In addition, other creatures cannot discern you are multiple people by the way you walk or stand.

Panic!

At 3rd level, you’ve learned when to divide to conquer. When you take damage in your ‘combined’ form, as a reaction you may split into two creatures, your ‘split’ form, which appear within 5ft of where your ‘combined’ form took damage. Both of these creatures may, as part of the reaction, move equal to your movement speed, benefitting from the effects of the disengage action as they do. Once per short rest when you use this reaction to split, you may halve the triggering damage.

Coordinated Dodge

At 9th level, while you are in your ‘split’ form, if one half uses the Uncanny Dodge ability to mitigate damage from an attack, the other half may halve the damage of the next attack that hits it before the start of your next turn provided it has a movement speed greater than 0m. 

Ceaseless Arguing

At 9th level, you learn to leverage your constant arguing to confuse enemies. If you are in your ‘combined’ form, or if both halves of your ‘split’ form are within 5ft of each other, when you attack, you may choose to taunt or bicker. When you do so, the creature you attacked must make a Wisdom saving throw. The save DC is equal to 8 + Your Proficiency Bonus + Your Charisma Modifier. 

 

• Taunt: If you chose taunt and the target fails the saving throw, they have disadvantage on attacks against creatures other than you until the beginning of your next turn. Creatures who are immune to being charmed are immune to this effect.

• Bicker: If you chose bicker and the target fails the saving throw, they have disadvantage on attacks against you until the start of their next turn. Creatures who are immune to the frightened condition are immune to this effect.

 

You may use this ability a number of times equal to Your Charisma Modifier (minimum 1). You regain all expended uses of this ability upon a short or long rest. 

 

Combined Assault

Starting at 13th level, you’ve learned to work together on the battlefield. When you take the attack action on your turn, you may take an extra attack provided the second attack fits the following parameters. This ability does not stack with other abilities that let you take additional attacks such as Extra Attack or Thirsting Blade. 

• If you are in your ‘combined’ form, you may make a second thrown attack with a dart
• If you are in your ‘split’ form, you may make a second melee attack with a dagger, provided the half making the second attack is not the same as the one who made the first attack

Provided you meet the requirements to apply sneak attack, your second attack may benefit from sneak attack even if you have already applied sneak attack this turn, doing sneak attack damage equal to the sneak attack damage of a rogue a third (rounded down) of your rogue level. 

Launch Maneuver

You have put your heads together to create the ultimate tactical strike. At 17th level, if you are in your ‘combined’ form, you may use a bonus action to enter your ‘split’ form, giving one half a flying speed of 60ft until the start of your next turn. If you make an attack while flying as a result of this ability, the target of that attack must make a dexterity saving throw against a save DC equal to 8 + Your Proficiency Bonus + Your Dexterity Modifier. If the attack hits, for each 10ft you flew in a straight line before hitting the target, you may deal an additional d6 on a failed save to a maximum of 6d6, or half as much on a successful save. While in your ‘split’ form, a half may ask (no action required) a willing creature within 5ft to use their reaction to launch you, giving that half the benefits of Launch Maneuver. The damage from Launch Maneuver may only be applied once per turn. You may use this feature a number of times equal to your dexterity modifier (minimum 1). Having another creature use their reaction to give you the benefits of Launch Maneuver counts as a use of it. You regain all expended uses of launch maneuver upon a long rest.