Conversion Kit: Assassin

Kit Overview

• Investment Type: Multiclass Dip

• Minimum Investment: Take 3 Levels of Rogue, selecting the Assassin archetype at level 3.

• Overall Impact: Your character now has the mechanical backing to follow through on clever schemes with lethal force.

Investment

Much like our last conversion kit, once you select the Assassin subclass, you can immediately set off to do what assassins do best. Once again, you'll need to satisfy the multiclassing requirement- just a score of 13 in Dexterity, plus a score of 13 in whatever attribute your other class of choice requires.

You don't necessarily need a Dexterity higher than this, but remember that your bonus to Stealth rolls keys off of it. You can mitigate the problems of a low Dexterity score by taking proficiency in Stealth and using the Rogue's Expertise feature to double your proficiency bonus.

Truth be told, you can abandon Stealth entirely if it doesn't fit your concept. However, you'll want to keep in mind that the assassin's primary feature requires Surprise. While by the Rules as Written, Stealth is the only way to gain surprise, many GMs will allow betrayals or sudden strikes to grant surprise.

Perhaps you can take advantage of Deception or Persuasion to lure your target into a false sense of security, or use a spell like Dimension Door or Invisibility to suddenly appear behind (or even before) a foe and strike them down.

All that said, regardless of the method you'd like to use, you're very likely to want stealth proficiency. It's the least reliant on GM interpretation and applies to the greatest variety of situations.

Narrative Impact

Though the most apparent Narrative for a character using this kit is that of a professional murderer, it is by no means the only route you can take.

Your character is now mechanically incredibly reliant on first strikes. Hunters-turned-warriors (such as most rangers) gravitate to this approach to combat by default, but characters lacking the stomach for battle might turn to this path to end fights quickly. Elite warriors might prefer ambush tactics, and even certain paladins may find a swift death to be all that their foes deserve.

In truth, you could utterly ignore this kit's narrative impact and carry on as if you had never taken a single level in another class. However, I'm inclined to see that as something of a wasted opportunity to set your character apart- where did your character learn to fight dirty? Do they see it as a necessary evil and regret their actions, or do they believe they're justified as there's no justice on the battlefield?

Mechanical Impact

From a mechanical perspective, the Assassin offers lethal first-strikes. Whatever your method of attack- a greatsword, a spell, thrown dagger- your Assassinate feature guarantees you a Critical Hit, as long as the attack hits a surprised target.

I cannot emphasize enough how unbelievably good a Guaranteed Critical Hit is in Fifth Edition D&D, and believe me, if I had a way to highlight that bolded, italicized, underlined phrase I would use it. I thought about including a gif of someone slapping a desk. I need you to see those words and realize what they mean.

A critical hit multiplies all of your damage dice. If you can find bonus dice, you're going to hit incredibly hard. If you have multiple attacks, they will all be critical hits. A critical hit on a Paladin's Smite or Rogue's sneak attack is a lucky break. A full round's worth of critical hits on a Fighter's attack routine or a Wizard's Scorching Ray is a dream. Get the drop on an enemy, and that dream is your reality.

The simple truth is, the Assassinate feature alone is enough to enable ambushes as a tactic.

Kit Support

There are several feats you can take advantage of to make this kit more effective. However, even if feats aren't allowed in your game, or all of yours are already accounted for, you're not out of luck. If you keep some rules of thumb in mind, you'll find yourself faring better than someone who approached their build haphazardly.

This list is in no particular order. This is not an optimization guide, and I don't want to commit to the math necessary to rank these options, nor do I want to limit your creativity. That said, as an Assassin, you want to look for:

• More attacks. These are easy enough to get: engage in two weapon fighting, pick a class that has the Extra Attack feature, or find a way to get Haste applied to you.

• Extra dice for your attacks: Smite and Sneak Attack are good examples. If you have your eyes on a higher level Rogue feature, the extra sneak attack dice will help with this (if you're using an appropriate weapon).

• Similarly, spells that grant multiple attack rolls such as Eldritch Blast or spells that have large dice counts like Chaos Bolt. Both of those can be picked up by classes that can't normally access them using the Magic Initiate feat.

You might also consider certain feats, depending on your build and game:

• Alert gives you a large bonus to initiative. Depending on how your GM runs Surprise, you may need to win initiative to take advantage of Assassinate- Alert all but guarantees that you'll move first, especially if your Dexterity is already high.

• Lucky adds some reliability to your assassination attempts by letting you try again when you roll poorly. Lucky is good to the point of being considered 'cheese' by the community, and many games ban it, but there is objectively no better way to ensure you don't ruin your big moment.

• Skulker is somewhat similar to Lucky for ranged characters, though not as effective. If you're a ranged Assassin, this keeps your position from being revealed. You'd be hard pressed to convince your DM that the enemy is still surprised, but maybe you can retreat and try again. The other miscellaneous stealth bonuses are a nice plus.

• Spell Sniper doubles your range for attack roll based spells- it'll be easier to surprise foes from a couple of hundred feat away. As a bonus, you ignore all but total cover and even get access to an attack roll based cantrip if you didn't have one already.

• Actor might improve your odds of pulling off a social skill based assassin, just check with your GM to make sure they'll rule in your favor before you invest too heavily in the approach.

Pitfalls

There's not a whole lot you can do as a player to make this kit go wrong. Your biggest obstacles are overspecialization and, potentially, your DM.

In the first case, there will be times when Assassinate will fail you. Perhaps the situation isn't right, perhaps you missed your attack, maybe the enemy got the drop on you. None of that matters though- just keep in mind when making choices about your character that not everything needs to improve their critical damage. Dealing hundreds of points of damage with your first strike only matters if you pull it off.

In the second case, some DMs are combative. You might have a DM that feels as though you're somehow "cheating" by assassinating big threats and coaxing your party towards ambush tactics. Some DMs will simply grumble about it and you may need to back off somewhat.

Others will attempt to sabotage you, either by presenting scenarios that make assassinations difficult or impossible, overwhelmingly pitting you against foes that are impossible to surprise or are immune to critical hits, or, in the most egregious cases, abusing their power and arbitrarily depriving you of surprise when you should have it.

The best thing you can do here is keep a level head and talk to your DM. They likely don't actively want to ruin the game for you, and perhaps they have a reasonable motive- maybe you're taking the spotlight away from other players or even making the game less fun for the DM themselves (believe it or not, this is a reasonable concern for the DM- they should have simply been honest with you in the first place, but berating them now won't help either of you).

Whatever your DM's reasons, you can likely compromise if they're honest with you. If your DM gives you any variation of "this is your fault for picking a specialized feature" or "it's just the way it is", you may need to ask if you can rebuild, as they're unlikely to sympathize with your position. Ultimately, your playstyle may just not align with the DM's or group's. There are hundreds of articles about conflict resolution, some specifically tailored for D&D groups, so for the moment I'll table the specifics.

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A Few Suggestions

I don't want to leave this article on a low note, so I'll close with some classes you can combine with the Assassin subclass for some exciting (if somewhat obvious) character concepts:

• Way of Shadow Monk: This monk path offers several supernatural abilities relating to darkness, silence, and hiding- not the least of which is the ability to teleport between patches of shadow. If that doesn't scream "ninja" to you, I don't know what will. The monk also has access to Flurry of Blows, which can make your assassinations quite potent.

• Oath of Vengeance Paladin: The Paladin's Smite might be the easiest on-demand way to take advantage of your Assassinate feature. Very few of this Archetype's features synergize with this kit, but access to Haste and Hunter's Mark doesn't hurt, and the narrative of an avenger fits well with the style of combat you'll be employing. If you liked Pathfinder's inquisitor class, this may be for you.

• Fiend Patron Warlock: Eldritch Blast is always good, but you have an extra edge with it. Honestly, there's not much too this other than having an easy on-demand ranged damage option, but something about being a contract killer for your Patron seems like an exciting narrative. Works just as well for other patrons, but the fiend seems most likely to employ contract killers. You can take the Blade Pact Boon and Eldritch Smite invocations if you want to step on the Paladin's turf.

With some examples out of the way, I'll take my leave. There's near limitless potential for this kit, as there's some synergy to be had with nearly every class, so you can experiment with confidence.

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Update: 12/12/2020

Additional Kit Support from Tasha's

It's a good day to be an Assassin thanks to some new feats found in Tasha's Cauldron of Everything. Each of these feats grants a bonus effect on a critical hit- and guess what you're already really good at?

• Crusher benefits those who use bludgeoning attacks- not the assassin's usual fare, but it could make your character stand out. This will allow you to position enemies with your attack- a fine support option, but its critical effect makes you an excellent ambush leader. After a successful use of the Assassination feature, or a lucky crit, all attack rolls against the creature get advantage until the beginning of your next turn. (If the creature survives your opener, that is).

• Piercer benefits piercing attacks, which is a common damage type for rogues. This is bonus damage, pure and simple. Reroll your low damage dice once per turn, and roll an additional die when you crit. A fair few ranged weapons deal piercing damage, so this feat has a slight edge in versatility.

• Slasher benefits slashing attacks, which are quite easy to come by. This is a skirmisher's feat. Your attack can now cut an enemy's speed, but more importantly, your critical hits now impose disadvantage on all of your targets attacks, giving you one crucial turn to finish them off or make a quick get away.

• Poisoner is no better for an assassin than anyone else, but a little bit of extra damage doesn't hurt when you're relying on one big attack, and poisoned is a devastating condition that can buy you time to finish fights.