A small, winged thief flying off with a potion.

Brazen Borrower by Eric Deschamps

Last time, I wrapped up my ranger subclass rankings. Now, it’s time for the rogue. As a reminder, there are three main categories I’m looking at as I judge the power level of each subclass: combat strength, allowance for a range of powerful builds, and how it interacts with multiclassing. Since the rogue has nine subclasses, this is a two-part post, starting with the bottom five.

9. Thief

A thief repelling down the side of a building.
Jhessian Thief by Miles Johnston

Rogues in 5th Edition occupy a unique position in the pantheon of martial classes. Instead of the Extra Attack mechanic other martials use to keep their damage relevant, rogues rely entirely on a single high-damage attack by using their Sneak Attack bonus. The problem is, Sneak Attack alone does not provide a particularly strong offense. Combined with the class’s generally lower AC and hit points, that means rogue subclasses need to make up for those weaknesses. Unfortunately, the Thief fails massively in this regard.

Level 3 – Fast Hands

You can use the bonus action granted by your Cunning Action to make a Dexterity (Sleight of Hand) check, use your thieves’ tools to disarm a trap or open a lock, or take the Use an Object action.

The options granted to all rogues by Cunning Action* will almost always be stronger than the ones offered by Fast Hands. Disarming a trap or opening a lock are rarely actions taken in combat at all, and if there is cause to use them, it can probably wait until the fight has ended. Using an object is slightly more useful, with items like the Healer’s Kit coming to mind, but even that is niche enough that I don’t consider it a major power boost.

Level 3 – Second-Story Work

When you choose this archetype at 3rd level, you gain the ability to climb faster than normal; climbing no longer costs you extra movement.

In addition, when you make a running jump, the distance you cover increases by a number of feet equal to your Dexterity modifier.

This feature is also very bad. The first half essentially grants the Thief a climb speed, but it doesn’t grant any bonuses to athletics checks that are often required when using said speed. Since rogues are generally dexterity based, their strength is usually garbage, making it difficult to use this pseudo climbing speed.

The second half of this feature has a similar problem. Jumping keys off of strength, and this feature doesn’t allow the rogue to substitute their dexterity for those calculations. Even if Second-Story Work did allow for these substitutions, they wouldn’t be enough for me to consider it a strong ability. In its current state, it’s awful.

Level 9 – Supreme Sneak

You have advantage on a Dexterity (Stealth) check if you move no more than half your speed on the same turn.

This is the first decent feature the Thief has gotten so far. When not in combat, this essentially translates into constant advantage, since speed is rarely an issue. In combat, the movement restriction is an actual cost, but a minor one. The problem with Supreme Sneak is that rogues are already so good at stealth that they don’t need advantage that often. This problem gets even worse in two levels when Reliable Talent* comes online, raising the skill floor for many rogues’ stealth checks to the low 20s.

Level 13 – Use Magic Device

You ignore all class, race, and level requirements on the use of magic items.

The power of this ability is entirely reliant on the magic items present in a campaign. If the Thief has access to Robe of the Archmagi and doesn’t want to multiclass, then this will feel great. However, the Thief could also wind up in a campaign where they never find a magic item that they both want to use and normally couldn’t. Personally, I’m not impressed, given that even if this feature does come up, a single level of multiclassing often accomplishes the exact same thing.

Level 17 – Thief’s Reflexes

You can take two turns during the first round of any combat. You take your first turn at your normal initiative and your second turn at your initiative minus 10. You can’t use this feature when you are surprised.

Finally, a good feature, and it is very good. People constantly extol the virtues of Action Surge, and that only allows the use of an additional action. This grants an entire second turn. Unfortunately Action Surge is gained at level 2 and this is stuck all the way at 17. I’m glad that the Thief has one unequivocally good ability, but sadly it comes too late to make up for all the bad that came before.

The Thief occupies the same space as the Champion fighter and Hunter ranger, serving as the most generic version of the class. Of these three, the Thief is easily the worst, granting little in the way of combat bonuses. Even out of combat, the Thief is weaker than the competition. This criminal scum gets stopped at ninth place.

8. Assassin

An assassin with a bloody knife.
Hooded Assassin by Matt Stewart

Moving on to the second of three Player’s Handbook rogue subclasses, we come to the Assassin. Where the Thief was weak because it lacked robust mechanics, the problem with the Assassin is it centers its strongest feature around something that it has no control over.

Level 3 – Assassinate

You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

Right away we come to the feature players select this subclass for. Looking at the first half of this ability, the Assassin can sometimes get advantage once per combat. Seeing as Tasha’s gave all rogues conditional advantage* as a bonus action, this isn’t much to write home about.

The second half of this feature, however, is much more interesting. Critical strikes, especially paired with a large dice pool like Sneak Attack, can be incredibly deadly. If an Assassin were able to reliably trigger these free crits, this would be one of the best rogue subclasses. Unfortunately, there is simply no way to gain this reliability.

There is no concrete way to make enemies count as surprised; it is completely up to the GM. Would leaping over a castle wall to attack a guard from stealth count as surprising them? What about sneaking into a camp and shooting into tents while they sleep? The answers to those questions will vary wildly from table to table, making this ability unreliable.

There is also the problem that surprise is a condition that ends once the creature takes its first turn. This means that the rogue needs to both surprise their opponent and beat them on initiative. There are of course ways to tilt initiative in the rogue’s favor, but it’s one more hoop that needs to be jumped through.

The final issue is one of overkill. If the GM interprets surprise to mean an extra round for the attackers, the fight is pretty much won regardless of special abilities. It doesn’t matter if the Assassin rogue gets a free critical hit, because it’s overshadowed by the free round of murder the party gets.

Level 3 – Bonus Proficiencies

You gain proficiency with the disguise kit and the poisoner’s kit.

Flavor tool proficiencies are niche at best. Disguise is probably the stronger of the two, as it can mimic the effect of some low-level spells, but the prevalence of those very spells means that the tool is often redundant even if there is call to use it. The Poisoner’s Kit does literally nothing unless you have the special ingredients, usually specific monster parts, to make poison with. Most of these poisons are pretty bad, and even the best of them use the poison damage type, the most common immunity in the game.

Level 9 – Infiltration Expertise

You can unfailingly create false identities for yourself. You must spend seven days and 25 gp to establish the history, profession, and affiliations for an identity. You can’t establish an identity that belongs to someone else. For example, you might acquire appropriate clothing, letters of introduction, and official-looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.

Thereafter, if you adopt the new identity as a disguise, other creatures believe you to be that person until given an obvious reason not to.

This is one of those features that is looking to solve a problem that shouldn’t even exist. If one of my players were to ask me if they could spend time and money to establish a fake identity, I wouldn’t scan their sheet for Infiltration Expertise; I would say yes and call for a relevant roll.

Setting this design issue aside, this feature has some mechanical problems. The main one is that it takes a week to use this ability. Depending on the campaign, a week can mean anywhere from part of one session to five or six sessions. 5E is very bad at handling timescales outside of a single long rest, and this feature is no exception. Finally, the reward for using Infiltration Expertise is very small for the level and time investment it requires. A combination of forgery, disguise, deception, and persuasion easily mimic this feature, and they’re available to all characters.

Level 13 – Impostor

You gain the ability to unerringly mimic another person’s speech, writing, and behavior. You must spend at least three hours studying these three components of the person’s behavior, listening to speech, examining handwriting, and observing mannerism.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

This feature suffers the exact same problem as Infiltration Expertise. It’s weak, niche, and something I’d probably let my players attempt without this ability.

Level 17 – Death Strike

When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.

This feature relies on the same mechanic as Assassinate and shares all of its issues. If you’re able to reliably generate surprise, then you will murder most enemies with attacks dealing four times damage. This ability has the extra wrinkle that it includes a save that targets a strong monster stat, but that is overshadowed by the surprise issues.

When I first started playing 5E, I thought pretty highly of the Assassin, but as I’ve learned more about the game and all the issues this subclass has in actual play, that estimation has fallen substantially. It’s no surprise the Assassin takes sixth place.

7. Inquisitive

A man with two swords and a fancy hat.
Elite Inquisitor by Jana Schirmer & Johannes Voss

Moving on from Player’s Handbook subclasses, we shift focus to Xanathar’s with the Inquisitive.* I see what the designers were trying to do, bringing the fantasy of the skilled interrogator to life. Unfortunately, it doesn’t quite hit the mark.

Level 3 – Ear for Deceit

Whenever you make a Wisdom (Insight) check to determine whether a creature is lying, treat a roll of 7 or lower on the d20 as an 8.

A bonus to a niche use of a single skill outside of the rogue’s main attributes isn’t the most exciting feature in the world. Thankfully, it’s not alone.

Level 3 – Eye for Detail

You can use a bonus action to make a Wisdom (Perception) check to spot a hidden creature or object or to make an Intelligence (Investigation) check to uncover or decipher clues.

Unfortunately, this ability does little to help. Enemy creatures rarely hide, making the bonus action perception check very niche. Checking for clues is almost never done in combat, not to mention that intelligence is even more likely to be weak on rogues than wisdom is, making that “boost” almost completely useless.

Level 3 – Insightful Fighting

As a bonus action, you can make a Wisdom (Insight) check against a creature you can see that isn’t incapacitated, contested by the target’s Charisma (Deception) check. If you succeed, you can use your Sneak Attack against that target even if you don’t have advantage on the attack roll, but not if you have disadvantage on it.

This benefit lasts for 1 minute or until you successfully use this feature against a different target.

This is the main 3rd-level feature for the Inquisitive. While it’s better than the last two, it’s still not great. The first issue is that Sneak Attack in 5E is easy enough to obtain for all rogues* that adding a special way to access it is a relatively minor boost.

The second problem is the new Tasha’s option: Steady Aim, which allows the rogue to gain advantage as a bonus action if they don’t move. Put these issues together and Insightful Fighting is left without a place to shine.

Level 9 – Steady Eye

You have advantage on any Wisdom (Perception) or Intelligence (Investigation) check if you move no more than half your speed on the same turn.

Since most perception and investigation checks are made out of combat when speed doesn’t matter, this feature basically grants advantage to both these skills for free. Two situational bonuses to relatively weak rogue skills still isn’t amazing, but at least perception is a heavily utilized skill.

Level 13 – Unerring Eye

As an action, you sense the presence of illusions, shapechangers not in their original form, and other magic designed to deceive the senses within 30 feet of you, provided you aren’t blinded or deafened. You sense that an effect is attempting to trick you, but you gain no insight into what is hidden or into its true nature.

You can use this feature a number of times equal to your Wisdom modifier (minimum of once), and you regain all expended uses of it when you finish a long rest.

Features like this are awful when they’re the paladin’s Divine Sense, and they’re awful here as well. This particular flavor of detection could be used to identify the presence of fake walls or other illusory terrain, although even that is of limited use since Unerring Eye doesn’t tell anything other than the existence of such an effect. The same could be said for detecting a shapeshifter trying to deceive the party, along with the same issues. This ability is so incredibly situational it would be bad a level 1. At level 13, it’s almost not worth mentioning.

Level 17 – Eye for Weakness

While your Insightful Fighting feature applies to a creature, your Sneak Attack damage against that creature increases by 3d6.

Now the Inquisitive has a legitimate reason to use Insightful Fighting. At 17th level, 3d6 isn’t a massive damage boost, but at least the damage is consistent.

The Inquisitive feels a bit lost mechanically. The flavor means it focuses on a small selection of skills, but rogues can already make themselves incredibly good at whatever skills they want, so it doesn’t feel like it’s bringing anything new to the table. Seventh place to the Inquisitive.

6. Scout

An armored woman with spear and shield.
Hyrax Tower Scout by Micah Epstein

Continuing with Xanathar’s, we have the Scout. This subclass mirrors the flavor of the ranger with a few mechanics to match. Thankfully, it also does a bit more to shore up the base rogue’s weaknesses.

Level 3 – Skirmisher

You can move up to half your speed as a reaction when an enemy ends its turn within 5 feet of you. This movement doesn’t provoke opportunity attacks.

Survivability is a problem that many rogues struggle with. This ability allows the rogue to duck in and out of combat, retreating from anyone who gets close enough to hit back. Using hide as a bonus action to drop off the map completely is a better defensive move, but it’s nice to have a reaction option as well.

Level 3 – Survivalist

You gain proficiency in the Nature and Survival skills if you don’t already have it. Your proficiency bonus is doubled for any ability check you make that uses either of those proficiencies.

Since wisdom isn’t one of the main rogue stats, these skills probably won’t be terribly high, meaning this feature makes the rogue decent at these instead of an expert. There is also the problem that nature and survival are niche skills compared to perception or stealth.

Level 9 – Superior Mobility

Your walking speed increases by 10 feet. If you have a climbing or swimming speed, this increase applies to that speed as well.

Now the scout has a bit more speed to keep enemies away from them. Since rogues don’t have a way to gain climb or swim speeds, the second half of the feature only matters if you can gain the speed through their ancestry or multiclassing.

Level 13 – Ambush Master

You have advantage on initiative rolls. In addition, the first creature you hit during the first round of a combat becomes easier for you and others to strike; attack rolls against that target have advantage until the start of your next turn.

Advantage on initiative is always good, making this half of the feature universally strong. The second half is also strong, allowing the Scout to pick one enemy for the entire party to gang up on. Any character that relies on attack rolls will be happy to have a Scout with Ambush Master on their team.

Level 17 – Sudden Strike

If you take the Attack action on your turn, you can make one additional attack as a bonus action. This attack can benefit from your Sneak Attack even if you have already used it this turn, but you can’t use your Sneak Attack against the same target more than once in a turn.

Now the Scout gets to make an additional attack, and they even get to use their sneak attack a second time. There is the drawback that the Scout needs to spread out their damage, so this doesn’t work once there’s only one enemy left, but before that it is a very good damage boost.

While the Scout has some good late-game features, it falters in the early levels. It’s a whole lot better than the previous entries, but the Scout can’t get away from sixth place.

5. Mastermind

A cloaked figure wearing a hood.
Lazav, Dimir Mastermind by David Rapoza

The closest thing to a support subclass the rogue has, we come to the Mastermind. While I like the idea of a rogue pushing their party to tactical supremacy, I don’t think it does enough to fully embrace the idea.

Level 3 – Master of Intrigue

You gain proficiency with the disguise kit, the forgery kit, and one gaming set of your choice. You also learn two languages of your choice.

Additionally, you can unerringly mimic the speech patterns and accent of a creature that you hear speak for at least 1 minute, enabling you to pass yourself off as a native speaker of a particular land, provided that you know the language.

Some flavor proficiencies and the bad feature Assassins received at level 13 isn’t great. I’m glad the Mastermind still has the possibility of a good 13th-level feature, but that’s about it.

Level 3 – Master of Tactics

You can use the Help action as a bonus action. Additionally, when you use the Help action to aid an ally in attacking a creature, the target of that attack can be within 30 feet of you, rather than within 5 feet of you, if the target can see or hear you.

This is the big support feature Masterminds receive. Not only can they Help as a bonus action, but they can do so at range. Interestingly, one of the classes that benefit most from the Mastermind would be a second rogue, as they need to make sure their powerful Sneak Attack lands.

Level 9 – Insightful Manipulator

If you spend at least 1 minute observing or interacting with another creature outside combat, you can learn certain information about its capabilities compared to your own. The DM tells you if the creature is your equal, superior, or inferior in regard to two of the following characteristics of your choice:

  • Intelligence score
  • Wisdom score
  • Charisma score
  • Class levels (if any)

At the DM’s option, you might also realize you know a piece of the creature’s history or one of its personality traits, if it has any.

I’ve covered features like this with the Battle Master fighter and Monster Slayer ranger. They were bad then, and they’re bad now. This ability requires a prohibitive amount of time to activate, doesn’t grant exact information, and forces you to choose which pieces of bad info you get.

Level 13 – Misdirection

When you are targeted by an attack while a creature within 5 feet of you is granting you cover against that attack, you can use your reaction to have the attack target that creature instead of you.

The real power of this feature is that it makes the GM dig up the cover rules to make sure they’re using them correctly. Once all the rules issues have been dealt with, this is a potent feature. Although of limited use against melee combatants, as they can reposition before attacking, the Mastermind can use an enemy as cover from enemy ranged attacks and redirect some of those attacks toward their living shield.

Level 17 – Soul of Deceit

Your thoughts can’t be read by telepathy or other means, unless you allow it. You can present false thoughts by succeeding on a Charisma (Deception) check contested by the mind reader’s Wisdom (Insight) check.

Additionally, no matter what you say, magic that would determine if you are telling the truth indicates you are being truthful if you so choose, and you can’t be compelled to tell the truth by magic.

Sadly, this feature is little more than flavor. Telepathy is rarely used against player characters, so being able to defeat it is very weak. Thankfully, the Mastermind had some decent abilities at earlier levels to make up for this nothing of a capstone.

I wish the Mastermind had embraced the support rogue idea. Abilities like allowing allies to hide mid-combat using the rogue’s stealth or granting some sort of sneak attack bonus to their friends would have fit perfectly in this subclass. All the schemes in the world wouldn’t take Mastermind higher than fifth place.

That covers the first five rogue subclasses. Check in next time for part two, when I cover the sneakiest of the sneaks.

I have also created a tier list for those of you who are interested.

Treat your friends to an evening of ritual murder – in a fictional RPG scenario, of course. Uncover your lost memories and escape a supernatural menace in our one-shot adventure, The Voyage.

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