Behind Every Tasha’s Cauldron of Everything Sidekicks Stands a Great Adventurer

Adventurers in fifth edition Dungeons & Dragons games I’ve run are no strangers to sidekicks whether they’re hired help, apprentices, spelljamming vessel crew or something else. I dug sidekicks when they were introduced through Unearthed Arcana, made their official debut in Dragon of Icespire Peak and most certainly in their expansion found in Tasha’s Cauldron of Everything. The sidekicks material in the book provides wonderful guidelines for incorporating these helpful creatures into your 5E D&D games. So let’s get into it.

Bullywug, goblin and tabaxi spellcaster sidekicks as seen in the fifth edition Dungeons & Dragons Tasha’s Cauldron of Everything. [Image courtesy Wizards of the Coast]

Get your 5E D&D kicks with new sidekicks

No doubt the fantastic new character options in Tasha’s Cauldron of Everything reinvigorate players around the world eager for exciting new content like subclasses and alternative class options. But for me the book’s juice is in chapter 4’s Dungeon Master’s Tools. Using and modifying existing creature stat blocks or creating new ones from scratch to represent allies for 5E D&D adventurers and parties is nothing new. Now we’ve got some robust support to develop and customize sidekicks including support for players to take on the role of these simplified characters.

Rules for sidekicks point to taking a creature with a low challenge rating and giving it levels in one of three simple classes — Expert, Spellcaster or Warrior. Any 5E D&D creature with a stat block and a challenge rating 1/2 or lower is eligible to become one of these sidekicks. For those keeping score that’s currently 417 creatures from official sources from the timid almiraj to the ferocious zorbo. From here it’s a simple matter of adding a sidekick class to the stat block.

Sidekicks start at the average level for a group and each class includes a chart detailing the proficiency bonus and any features gained level by level just like a standard character class. When a group’s average level goes up sidekicks gain a level too, which includes increased Hit Dice and maximum hit points. Like a regular character sidekicks fall unconscious when they drop to 0 hit points and make death saving throws. In the same manner their to hit modifiers and DCs of abilities increase when their proficiency bonus goes up as well as any other features related to ability scores when these increase.

I particularly think it’s super cool how the sidekicks rules indicate a potential sidekick must be the friend of at least one adventurer. This speaks to 5E D&D’s guidelines for social interaction, which point players to the game’s less crunchy but no less vital components like personality traits and background. A sidekick’s friendship could be related to a character’s backstory for example, or background elements like a knight’s retainers or even an urchin’s pet mouse.

Who plays sidekicks is left to a group decision and continues a strong theme I’ve noticed in Tasha’s Cauldron of Everything — collaboration. Many parts of the book use language to foster group participation, which is totally awesome. In the case of sidekicks the book provides some possibilities like a player playing a sidekick as a second character, playing a sidekick as their only character, playing the sidekick collectively as a group or leaving their decisions and roleplaying to the DM.

In my 5E D&D experiences I’ve seen sidekicks employed several ways both before and after the release of content each step of the way. In my Spelljammer campaign players absolutely loved the myriad crew of unusual sidekicks. Some joined them after the group encountered them during adventures and others made the cut through recruitment drives the party held to supplement their crew. More than a few times players took on the roles of their sidekicks when people couldn’t make a session, they split up or sent various away teams to different places and in one case after a void dragon’s death effect sent a character and a handful of sidekicks to the Nine Hells quite unexpectedly.

Aasimar, firbolg and wolf warrior sidekicks as seen in the fifth edition Dungeons & Dragons Tasha’s Cauldron of Everything. [Image courtesy Wizards of the Coast]

5E D&D classes for sidekicks

“When you create a sidekick, you choose the class it will have for the rest of its career: Expert, Spellcaster, or Warrior… If a sidekick class contains a choice, you may make the choice or let the players make it.” — Tasha’s Cauldron of Everything

Expert. These sidekicks master particular tasks or specialize in certain knowledge, placing brains above brawn. Scouts, musicians, librarians, clever street kids, wily merchants and burglars represent a few examples Tasha’s Cauldron of Everything provides. Experts must be creatures with at least one language they can speak in their stat block. (But do they really? I’m 100% sure your Expert sidekicks could get by without such a restriction.)

Experts gain lots of skills and features very similar to rogues as they advance in level. In a recent campaign I ran one of the party’s sidekicks developed into something of a medical professional. The party often called on their assistance to make Wisdom (Medicine) checks and the like. It was pretty cool to watch this take place over several sessions since I incorporated this particular sidekick as a somewhat generic rogue meant to give the party some opportunities to scout and deal with traps.

Spellcaster. Sidekicks with this class walk the path of magic. Tasha’s Cauldron of Everything gives examples like hedge wizards, priests, soothsayers, magical performers or simply any creature with magic in their veins as representatives of these sidekicks. Like experts these sidekicks must have at least one language they can speak in their stat block but again, is it really necessary? I don’t think so.

Spellcaster sidekicks don’t gain a whole lot of class features but what they do gain as spells including cantrips all the way up to 5th level spells. They also start with a couple of skills to show their area of expertise. This sidekick class further differentiates with a role to specify whether they’re a mage, healer or prodigy. This role defines their spellcasting ability and spell recommendations. Their spellcasting grows more powerful through features like Potent Cantrips, Empowered Spells and Focused Casting.

Warrior. You won’t be surprised to learn these sidekicks hone their martial prowess as they fight side by side with adventurers. Soldiers, town guards, battle trained beasts and other creatures dedicated to combat are a few examples Tasha’s Cauldron of Everything gives for warrior sidekicks.

Warriors receive benefits similar to fighters as they climb the levels and start with a couple of skills along with a choice to focus their training as an attacker or defender. Features like Second Wind, Improved Critical and Improved Defense give them the tools they’ll need to hang with the big damn heroes.

New 5E D&D toys from Tasha’s Cauldron of Everything

Aside from the limitless potential for sidekicks in 5E D&D games as presented in the book there’s even more a DM might glean. Several of the sidekicks features could make wonderful rewards for adventurers too. For example an Expert’s Helpful feature could be a powerful boon granted to a character who often takes a support role for the rest of the party.

However you look at them sidekicks opens a door to terrific developments in your 5E D&D games. Personally I like the idea of a group taking collective ownership of a sidekick but I would certainly work together to establish some guidelines for this or else it could lead to frustration among the players.

At any rate I’m super excited to see sidekicks developed more in Tasha’s Cauldron of Everything. How about you? Have you used these sidekicks or something similar in your 5E D&D games? Let me know in the comments and of course as always stay nerdy!