Henchmen and Hirelings DnD 5e

Last Updated on March 7, 2024

In Dungeons and Dragons 5e, you can pay a hireling a set price for a distinct service. If you want to pay someone for long-term work, you call them a henchman, and you still pay for a certain service as opposed to a number of hours per day.

This leads us to the question:

Can You Hire Henchmen and Hirelings in DnD 5e?

Yes, you can. When hiring a hireling or henchman in DnD 5e, you must be aware of their costs, their services, and the extent of their abilities.

When To Hire a Hireling or Henchman

The Dungeon Master’s Guide has a section on what types of goods and services for which a PC could reach out to a hireling from courier services to a tailor, and this is just the tip of the iceberg.

Think about all the PCs don’t do for themselves. They don’t produce their own food, so they need to buy it either from a farm directly or from a processor in the middle, such as a butcher, a baker, or a candlestick maker (because no one likes to eat in the dark).

Everyone in this process is either a worker, a merchant, or a hireling. So the next time PCs need something done or provided, like a fine set of clothes to impress the aristocracy, they should pay someone for it.


Instead of being paid for a particular service on a particular day, henchmen tend to stay on retainer and can be ordered to do a variety of jobs.

For this reason, henchmen tend to be better outfitted and have more complex stat blocks.

To Hire a Henchman:

1. Choose a monster from any published material, such as a Bandit or an Adept.

2. Pay them a retainer fee of 1 gp per CR (if their CR is less than one, give them a number of silver pieces representative of that fraction).

3. Give them work to do that they are capable of.

The Proper Care and Feeding of Henchmen:

Henchmen need to feel like their services are appreciated. Of course, you are paying them, but in general, they need to know you care. Offer them encouragement and bonuses for each successful job. The easiest way to do that is to let them have any loot they find while out working for you.

Ideally, your per-day fee will cover the cost of their room and board, but any other amenities you can offer would sweeten the deal and keep their attitude toward you securely in the positive realm.

Henchmen can be turned and swayed as their loyalty is not absolute, but the better you treat them, the less likely they are to jump sides.

So, throw in a gym membership. Why not?

How To Create a Skilled Hireling

When you need a skilled hireling, consider what exactly you need the hireling to do. Long story short, you need someone who is proficient in either a particular skill or a particular set of tools.

If you need a skilled hireling on the fly, give them a basic stat block of a common villager, and then double their HP, and give them the necessary bonus in the particular skill you need.

Skilled hirelings should be paid 1 silver per day for each +1 they have in that particular skill.

If you need a tracker and you find an NPC that has a +7 in survival, pay them 7 sp per day of tracking.

What follows is a list of all the skills in DnD 5e and what types of hirelings make their living from that skill. The occupations listed after each skill are nonexclusive, meaning a particular NPC could fulfill any of the roles dependent on that skill. You will simply have to negotiate how much pay they want.

(Incidentally, these occupations could also make for good downtime activities for the PCs if they ever decide to live a semi-honest life.)

  • Acrobatics (Dex) – spies, thieves, chimney sweeps, couriers, gutter cleaners, high-rise carpenters, performers
  • Animal Handling (Wis) – drivers of animal-powered vehicles, animal trainers, veterinarians
  • Arcana (Int) – researchers, librarians, educators
  • Athletics (Str) – manual laborers, couriers, athletes
  • Deception (Cha) – informants, any public relations position, hospitality management, legal workers, law enforcement, organized crime
  • History (Int) – educators, researchers, librarians
  • Insight (Wis) – informants, researchers, therapists, legal workers, hospitality management
  • Intimidation (Cha) – any public relations position, legal workers, law enforcement, organized crime, management class, union reps
  • Investigation (Int) – educators, researchers, librarians, law enforcement, legal workers, clerical workers
  • Medicine (Wis) – first responders, medics, pharmacists, apothecaries, hospitality management
  • Nature (Int) – trackers, foragers, agricultural workers
  • Perception (Wis) – educators, researchers, informants, law enforcement, librarians, trackers
  • Performance (Cha) – performers, hospitality management, any public relations position
  • Persuasion (Cha) – hospitality management, any public relationship position, legal workers, union reps, management class
  • Religion (Int) – educators, librarians, researchers
  • Sleight of Hand (Dex) – informants, pickpockets, locksmiths, gamblers, performers
  • Stealth (Dex) – informants, trackers, mercenaries, organized crime, law enforcement
  • Survival (Wis) – trackers, foragers, agricultural workers, long-term project manual laborers

How To Hire a Hireling or a Henchman

There are two types of skilled hirelings: independent contractors and gilded tradesmen.

Independent Business Owners

Independent business owners can have their goods and services purchased pretty much straight out of the published material in any of the Equipment chapters.

The cost of hiring such a product or service should simply be as printed in your sourcebook and assumed to be of usable material.

However, consider the PC’s lifestyle expenses. If they are paying for a comfortable, wealthy, or aristocratic lifestyle, they can afford better-quality goods and services.

For these PCs, charge half-again for comfortable, double for wealthy, and triple for aristocratic-level services. To reflect the quality of these services, offer a +1, +2, or +3 respectively when factoring in the use of the goods or services to any associated rolls.

For example, if your PC goes to a wealthy tailor for their clothes, offer them a +2 on Charisma-related checks when wearing those clothes. If they get an aristocratic-level weapon crafted, offer a +3 to attack for a limited time until wear and tear lowers the weapon’s quality.

Magical services provided by these hirelings should only be available to the higher socioeconomic classes unless you are playing in a magic-rich world.


Guilds of crafters, merchants, and tradesmen do exist. These hirelings are part of an extended network that carry with them the benefit of the guild’s reputation and resources.

These hirelings and henchmen should also only be available to the higher-level socioeconomic statuses, and their prices and products should be priced accordingly.

Common Adventure Trope

One common adventure trope that utilizes hirelings and henchmen is what I call the “Wal-Mart Wars” campaign.

In this type of story, the various business guilds have banded together and are attempting to completely control all business and economic activity in a given region, be it a town, state, or country. 

To accomplish this, the guilds are either pushing or buying out small businesses. Those small businesses are turning to local gangs for protection. While some gangs are taking their role as extortionists and community protectors seriously, others are simply working for the highest bidder — the guilds.

Therefore, the guilds are causing massive gang wars, and it is the individual business owners and their workers who are suffering.

When some workers threaten to unionize in order to have a say in how the guilds operate, the guilds hire the gangs and the guards to punish them even further.

Yet, throughout all of this, a certain charismatic guild leader is calling for a special election to make him the new mayor or governor, and he promises to crack down on crime — all while paying the gangs to do the dirty work for his own guild.

The PCs can enter into this conflict on any side they choose. They can work for the guilds to get the gangs in line, or they can work for a gang to be a part of a rebellion.

As a third option, they could be part of a gang that is attempting to become a guild, a la Peaky Blinders.

May all your 20’s be natural, my friends.

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