Halfling Rogue Character Guide: DnD 5e

For the halfling rogue mastermind build, consider the following:

Halflings make notoriously fun rogues, especially rogues who fall under a charismatic umbrella. It might just be me, but the Mastermind archetype seems to be great choice.  This character will still use thieves’ tools and have lethal ability with a rapier—a full-fledged rogue.

There’s no doubt halflings make great rogues and thieves, but let’s see how we can make this different.  We can make cooler, smoother. This character could be more Ocean’s Eleven in their thieving.

If you’re interested in a premade adventure full of casino games and pirate poker, check out my original Dead Man’s Tale by clicking here or below.

Deadman's Tale an Island Pirate Adventure DnD 5e friendly 3rd party campaign

Halfling racial traits

As I mentioned, halflings are natural rogues.  Stealthy, small and light on their feet, this race was built to burgal… so to speak.  As a racial bonus, they gain a +2 to Dexterity, the natural ability score of rogues.

There are, however, other racial abilities that contribute to a rogue.  Lucky is a racial trait that allows me to re-roll a d20 when I land on 1.  You’d be surprised how clutch this could be.  Halfling Nimbleness allows a halfling to move through the space of any creature that is of a size larger than my own.

More specifically, Ill choose the Lightfoot subrace of halfling.  This race receives a +1 bonus to Charisma as well, along with unique stealth moves.  Naturally Stealthy gives me the ability to attempt to hide while only obscured by a slightly larger creature.  It’s kind of hilarious and brilliant.  I’ll hide behind my party mates and sneak attack enemies.

Fundamental rogue abilities

As a rogue, I generally go with a rapier/short bow combination.  I’m fancy like Zorro.

Starting at level 1, Expertise, Sneak Attack and Thieves’ Cant start me down the right (or wrong) path.

Expertise grants me double the proficiency score in two of my skill sets, or one skill and the thieves’ tools.  I go for the thieves’ tools because of course I do.  The second skill is probably going to be stealth.  Who can’t use all the stealth as rogue?

Sneak Attack adds an extra 1d6 of damage once per turn if you have advantage.  In other words, if you sneak up on a guy, or the enemy can’t see you, that’s extra damage.  Plus, you don’t need advantage on the attack roll if a friend is near the target.  Of course, this damage increases as you level.

Thieves’ Cant, put plainly, is a secret language between thieves.  It’s like speaking in riddles, taking longer than ordinary language to comprehend. It also comes complete with a set of written runes. So, there’s that.

Cunning Action comes in at level 2.  This bonus action allows the rouge to Disengage, Dash or Hide.  In other words, you could potentially hide during combat, especially as a halfling who can hide behind people.  In turn, this will set up a Sneak Attack, where we get extra damage.  Everything works together.

Uncanny Dodge comes in at level 5, offering the ability to half combat damage inflicted as a reaction.  This will be crucial for a small, barely armored martial character.

And this is all baseline rogue stuff.  This little halfling is going to be dangerous.

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Mastermind special abilities

Here’s where we get the Ocean’s Eleven vibe.

Technically, the Mastermind archetype is more of an espionage agent.  These rogues are masters at infiltration and working people, so the extra +1 Charisma Lightfoot halflings receive will come in handy here.  At level 3, the Mastermind receives two abilities: Master of Intrigue and Master of Tactics.

Master of Intrigue grants proficiency with disguise kits, forgery kits and one gaming kit of your choice.  See what I mean?  It’s a rambling gambling dude ready to pull off a heist.  On top of this, you can make yourself sound like anyone you’ve listened to recently.  Thus, we have some of the espionage element to the character build.

Master of Tactics offers the Help action as a bonus action.  Being a charismatic, people-person sort of rogue, this will work well in a team dynamic.  Think of the tank character and how this little rogue can maneuver around that tank.  Our goal is to never pull aggression.  We’re trying to stab enemies in the back.

Implement the halfling “thief” trope

As always, I want to talk about character themes you can play with.

This character has a ton of personality to compensate for his size.  They’ll probably need a relatively high Charisma score, along with Dexterity.  We can play this style character in urban adventures or with groups who enjoy more of the character aspects of an RPG.

Let’s think of a few setups this character could have.

One could be the leader of a rag-tag gang of thieves, played by your real-life buddies.  Some of the gang could be fighters or spellcasters in hiding or rangers or rogues.  The biggest hit of the century is parading through town square: an arrogant prince on his way to a celebration.  Can you snag some goods off his caravan?

Another story could involve espionage, an agent for the king.  This character, along with a group of allies (the king’s loyal men, court wizard, chosen-one-farm-boy) could be on a mission.  What kind of mission?  To retrieve a letter that could stop a war.  Or maybe steal the kingdom’s mascot.

Either way, you have a smooth operator with this character combo.

Or, play as Bilbo Baggins

After all is said and done, we could totally play this as Bilbo.

At first, I thought “thief”, as the dwarves went on and on about him being a burglar.  In all reality, he was a mastermind.  He tricked Golem into a game of riddles and stole his ring.  He convinced Smaug not to fry him.  How could that not be the apex of Mastermind rogues.

So, if the need comes up, we have George Clooney or Bilbo Baggins, whichever fits the vibe of your game.  Maybe even James Bond?  Maybe.

Check out other mysterious D&D articles

How to Write and GM a Mystery Campaign

D&D 5e Guide to Playing a Ninja 

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