Last Updated on October 24, 2023
Bandit Captains are the leaders of a group of merry men, of thieves, of highwaymen, of outsiders on the fringes of society trying to survive or just to make a quick buck.
They might be cruel or cowardly, honest or pitiable, noble or simply looking for something to do that’s more interesting than raising sheep.
Only one thing unites Bandit Captains, and that’s their ability to lead others into battle or simply toward money. Bandit Captains are savvy, and they use that cunning to make as much money as easily as possible.
Sure, the threat of violence is always there, but an effective Bandit Captain is always looking to get the loot and to avoid getting shot.
Boy are they in for a surprise when they run into adventurers…
If you’re looking at running a Bandit Captain in your game, think you might be fighting one soon as a player, or are just looking for some interesting D&D flavor and tactics, you’ve come to the right place.
A Bandit Captain can be pretty much anyone — any Medium Size humanoid of any race and any non-Lawful alignment qualifies.
Bandit Captains have pretty decent stats and three saves. Their basic stats are:
- STR 15 (+2), DEX 16 (+3), CON14 (+2), INT 14 (+2), WIS 11 (+0), CHA 14 (+2)
- AC: 15
- Hit Points: 10d8+20 (65 average)
- Speed: 30 feet
- Skills: Athletics (+4), Deception (+4)
- Proficiency Bonus: +2
- Passive Perception: 10
- Languages: Any two
- Challenge Rating: 2
As you can see from the stats, Bandit Captains are well balanced and tough with boosts to their ability to lie and perform athletic maneuvers.
Their passive perception is nothing to write home about, but they have a decent amount of hit points and a good AC that comes from studded leather armor.
Bandit Captains also have several combat abilities.
They can Parry, which means as a reaction they can add 2 AC against any melee attack that would hit (as long as the Bandit Captain can see the enemy and is wielding a melee weapon).
They have Multiattack, which allows them to make two attacks with their scimitar and one with their dagger.
They can also simply make two ranged attacks by throwing their daggers. How many daggers a Bandit Captain has is up to your DM.
Both weapons have a +5 to hit and a reach of 5 feet, though daggers also have a range of 20/60. Scimitars do 1d6+3 slashing damage, and their daggers do 1d4+3 piercing damage.
Portrait of the Bandit Captain
Bandit Captains are all about their cohort, and it would be unusual to find them far from the bandits they command. However, that general guidance hides a variety of approaches to presenting and interacting with Bandit Captains.
Below are some general suggestions, but they are only a place to start. You should always craft your NPCs to your setting and your players.
Bandit Captains have a few simple priorities, though which of these take precedence in a given NPC is up to you.
A Bandit Captain is loyal to the people they lead, values their lives highly, and wants money by any means they can get it.
Bandit Captains are readily willing to lie about who they are and their motivations in order to achieve their aims or just stay alive.
If the party seems like they might be sympathetic to poor peasants, displaced refugees, or noble Robin Hood types, then that’s the story the Bandit Captain will present to them.
Living on the fringes as they do, Bandit Captains are also very likely to be suspicious and distrustful of kindness.
Remember though, that there’s no reason you couldn’t portray a Bandit Captain exactly as an honest scoundrel, a Robin Hood seeking to help the community and being labeled a bandit because of it.
A bandit captain will have only a few close relationships if any. They might have an inner circle among their cohorts, but this might be a treacherous series of relationships indeed.
They will, however, have strong bonds (whether of fear or love) between themselves and their band of thieves.
No one can lead others effectively into dangerous combat without some level of trust from their followers. Bandit Captains who fail to earn the loyalty of their compatriots will quickly find a knife in their back.
Bandit Captains are also likely to have a wide network of loose allies, contacts, suppliers, arm dealers, informants, and, if they’re very powerful, spies.
This kind of network is essential for someone in charge of a criminal organization, though if the bandits are four guys barely surviving the winter in the middle of the woods, you might want to scale this down.
For more successful bandits, an external supply of hard-to-get food or other supplies might be essential to successfully avoiding the law.
To make Bandit Captains really flavorful, I recommend giving them and their followers a theme. You might have a reflavored Bandit Captain also captain a ship, be the leader of a band of mercenaries, or run crime in a small town.
A generic Bandit Captain might be a temporary struggle for the PCs to beat, but they’ll remember a foe who tries to give them her business card after she’s been beaten.
Bandit Captain Tactics
The tactics of Bandit Captains will primarily revolve around the coordination of their followers.
On their own, Bandit Captains can be formidable for 2nd-level parties, but they will quickly become crushed by the action economy as players level up.
Even supplementing their combat power with magic items or better armor and weapons can only go so far. However, Bandit Captains with the resources of their allies behind them can be deadly.
While social combat isn’t really a thing in D&D 5e, Bandit Captains will readily use deception, trickery, and a silver tongue while engaging their foes.
When attempting to rob a group of PCs who turn out to be more powerful than expected, the Captain might make threats and try to extort a fee rather than outright fight. They may try to beg or barter for money as well as threaten.
Unaware PCs engaging in this kind of banter and parley might even be surprised by a sudden and almost invisible signal from the Bandit Captain who initiates combat.
When it comes to actual combat, a Bandit Captain will fight alongside their fellow bandits. This is usually done from ambush, ideally from behind half or three-quarters cover, and most effectively done from 80 feet away with a light crossbow and overwhelming numbers.
This ensures that any enemies capable of surviving the bolts have to close a distance that might take two or three rounds to cover before being able to strike back.
Bandit Captains are most likely to be found in positions where they can coordinate their forces, trigger traps, or direct their men.
Coordination can be invaluable, especially if the bandits are attempting to make themselves seem like a more powerful force than they actually are.
A few well-placed lines of string in the treetops connected to pre-set crossbows can do a lot to a player’s estimation of their chances.
Smaller groups of bandits might have their Bandit Captain leading the group and asking for the money themselves in order to display strength and competence.
In combat, Bandit Captains, as well as bandits themselves, value their own lives. If significantly injured, they will attempt to take the Dodge action and regroup with allies or potentially flee if their health is low enough.
They may also try to negotiate, even negotiating during combat. If neither fleeing nor negotiating is sufficient, a Bandit Captain, unlike a bandit, may be too proud to surrender.
A clever Bandit Captain may even carry a couple potions of alchemist’s fire on themselves for this very eventuality…
When facing bandits and Bandit Captains, PCs can easily fall prey to simple but effective tactics.
In order to counter strategies of ambush and ranged attacks, players need to take advantage of the magical resources they have as well as the higher AC scores that their wealth and magic allow for.
The Dodge action can be very effective in allowing martial players to close the gap between themselves and crossbows relatively uninjured. So can a simple casting of Fog Cloud, Minor Illusion, or Silent Image.
All three of these spells can effectively obscure the party’s location or at the very least provide some cover. Of these spells, Fog Cloud is the most effective.
While a party could potentially engage bandits in melee, being careful not to become surrounded and cut off from aid, this is not the optimal strategy.
Especially when facing a large number of opponents, there is no guarantee that the party might not simply become overwhelmed as they cut through the bandits.
Moreover, not all campaigns have short adventuring days. Defeating a group of 15 bandits and their captain in brutal combat may be possible for a large party of level-7 characters, but they will likely lose significant chunks of their health while doing it.
The Bandit Captain who tricks you into a pit of burning oil in the morning is the same Bandit Captain who ensures from beyond the grave that you don’t have quite enough health to survive that red dragon’s surprise breath weapon.
Instead, parties should take advantage of the certain cost-benefit calculation going through the Bandit Captain’s mind.
Are they worth the trouble? Do they have unexpected magics? Are these adventurers foolish enough to blunder into one of my fall back traps, or are they playing it smart? If I do manage to kill them, what will it cost me? Will I make enough money to keep the loyalty of those that survive?
While a Bandit Captain may not be obviously thinking these thoughts, you can bet they’re in the back of their mind somewhere.
A party that makes it clear they can fight smart and that they have enough strength to make a combat seriously contested will likely be extremely unappealing to a Bandit Captain.
Negotiations may ensue and may be best for all sides.
Alternatively, perhaps a party’s casters and martial characters can avoid/soak damage long enough for the rogue to sneak behind the Bandit Captain and make them seriously worried about how many hit points they have left.
Nobody wants to die, and bandits are perhaps more aware of how close to death they can come than the average person.
Clever players may be able to avoid a costly combat encounter all together or at least cut it quickly short with a win condition other than “kill everything that moves.”
Whether you’re a player or a DM, hopefully this analysis of Bandit Captains has been an effective way of not only estimating their strength and finding techniques for flavoring their character but also learning how to properly present their danger and weaknesses.
On their own, Bandit Captains can only provide a threat to low-level parties. Even if they were more powerful, the action economy rules supreme.
The Bandit Captain’s real threat is in their personality and character that has allowed them to surround themselves with allies.
With these allies and the threat of ambushes, traps, and tactics, Bandit Captains can make it clear to even adventuring parties why the roads are so dangerous (to a point anyway).
Their tactics can be as simple as crossbows several dozen feet away or as complicated as hidden pits, tricky deceptions, or allies hidden in the trees.
For Bandit Captains, it doesn’t have to be fancy, just effective and profitable.
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Growing up I spent most of my time reading, so when I first started playing RPGs in middle school and got a copy of DnD 3.5’s rules I loved their collaborative take on storytelling. These days I like to use RPGs to develop my creative problem-solving skills as well.