*WIP* 4th Ed Assassin to 5th Ed

So, my gaming group is going to be moving our old 4th ed game to 5th ed. For most of the group, this isn't an issue. However, some of us require a little of the ol homebrew to make our characters work.

After much searching, I found everything except for my own character, the Assassin (Dragon Magazine version). So, I'm working on my own conversion here.

In 4th ed, the assassin is a striker class, but 5th doesn't have this. The assassin is also a glass cannon: Hits hard but relatively fragile. I toyed with the idea of making this a new warlock pact and patron, but the Assassin isn't a spell casting class. So, I decided to make this a martial class, but with a D8 for hit points.

Also, since I decided to change the name of the class (though I'm not entirely happy with the name) to prevent any confusion with the existing Assassin class.

This is a work in progress, and I'm looking for input. One concern is the shrouds may be overpowered at low levels, but not powerful enough at higher levels. On the other hand, at low levels targets might die before the shrouds get used, so it might balance out?

As well, higher level abilities are misisng. I'm still working on these for completion sake, but again, I'm a little unsure of what appropriate higher level powers/damage would be.


Shadow Walker
"By the time you see me, it is too late to save yourself"

Hit Points
Hit Dice: 1d8 per Shadow Walker level
Hit Points at 1st Level: 8 + your Constitution modifier
Hit Points at Higher Levels: 1d8 (or 5) + your Constitution modifier per Shadow Walker level after 1st

Proficiencies
Armour: Light and shields.
Weapon: Simple Weapons, all one handed swords, light crossbow.
Tools: Thieves Tools
Saving Throws: Dexterity, Constitution
Skills: Choose three from Acrobatics, Arcana, Athletics, Deception, Insight, Perception, Stealth or Sleight of Hand.

Equipment
You start with the following equipment, in addition to the equipment granted by your background:
(a) a longsword or (b) a rapier
(a) a light crossbow and 20 bolts or (b) a shortsword
(a) a burglar’s pack, (b) a dungeoneer’s pack, or (c) an explorer’s pack
Leather armor, two daggers, and thieves’ tools

Shade Form: *flavor text*
As a bonus action, you assume a shadowy form that lasts until you make an attack roll or until the end of your next turn. While in this form, you are insubstantial, any attacks against you are at Disadvantage, you can move through people or objects as if they were difficult terrain, and you gain vulnerability to radiant. If you end your turn in a solid object, take 1D10 damage and you are shunted off to the nearest unoccupied space.
As a Bonus action, you can maintain Shade Form.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Shadow Step: *flavor text*
Instead of a Move Action, if you are adjacent to a creature, you can teleport up to 20 feet adjacent to another creature.

Shadow Shroud: *flavor text*
As a Bonus Action, you subject the target to your shroud. If any of your shrouds are already on the target, you subject it to an additional shroud, up to a maximum of four. The shrouds last until you use this power against a different enemy or until the end of the encounter. Before you make an attack roll against the target, you choose to invoke either all your shrouds on it or none of them. If you invoke your shrouds, the attack deals 1d6 damage per shroud, minus one shroud if the attack misses, and all your shrouds then vanish from the target. This damage roll never benefits from bonuses to damage rolls, and is in addition to the attack’s damage, if any.

Executioners Noose: *flavor text*
You target one creature up to 30 feet away and make a melee attack. If the attack is successful they take 1D6+dexterity damage. If the target is Large or smaller, you pull the creature up to 10 feet closer to you. This abilities damage increases by 1d6 when you reach 5th level (2d6), 11th level (3d6), and 17th level (4d6).

Cloak of Shades: While in dim light or darkness, you can take the Hide action as a bonus action.

Guild Training*flavor text*
Choose one of the following options. The choice you make gives you the benefit described below and also provides bonuses to certain Shadow Walker powers, as detailed in those powers.

Bleak Disciple: When you hit an undamaged target, you gain temporary hit points equal to your Constitution modifier. Add 2 to the temporary hit points gained at 11th level and 4 at 21st level.

Night Stalker: You gain a bonus to damage rolls equal to your Charisma modifier against any target that is adjacent to none of your enemies.

Haunting Shade: More of your essence has bonded with the Shadowfell, making you more at home in the dark places of the world. You gain a +2 bonus to stealth checks and gain darkvision out to 30 feet

Shadow Darts:*flavor text* Make three ranged attack rolls. If any of them hit, resolve them as a single hit, and all of them must miss for the attack to miss. 1d8 cold damage if one of the attack rolls hits, 2d8 cold damage if two hit, or 3d8 cold damage if three hit.

Once you use this feature, you can’t use it again until you finish a short or long rest.

Extra Attack: Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn. The number of attacks increases to three when you reach 11th level in this class and to four when you reach 20th level in this class.

Shadowy Escape: Starting at 6th level, you can vanish into the shadows in response to harm. When you take damage, you can use your reaction to turn invisible and teleport up to 60 feet to an unoccupied space you can see. You remain invisible until the start of your next turn or until you attack or cast a spell.

Once you use this feature, you can’t use it again until you finish a short or long rest.

Twilight Assassin: *flavor text*
You conjure a shadowy duplicate of yourself in an unoccupied square adjacent to the primary target. The duplicate occupies its space, and it lasts until the end of the encounter. Whenever you use a move action, you can also move the duplicate 30 feet. While the duplicate is adjacent to a target, you gain Advantage on attack rolls against it. As a bonus action, until the duplicate vanishes, it can make a regular melee attack against an adjacent target. If it hits, it does 3 points of damage, or 6 damage if the target is currently targeted by a shroud.
The duplicate can be targeted by attack, has an AC of 10+Dex bonus, and has half your hit points.

Darkspiral Aura: Starting at 14th level, when you hit a creature with an attack, you can use this feature to instantly transport the target down a well of impenetrable darkness. The creature disappears and plunges down an inky black vortex through the Shadowfell.
At the end of your next turn, the target returns to the space it previously occupied, or the nearest unoccupied space. If the target is not an undead, it takes 10d10 necrotic damage as it reels from its decaying experience.

Once you use this feature, you can’t use it again until you finish a short or long rest.

Version 2

So after a bit of tinkering, I think I found a good mix.

Shadowblade
"By the time you see me, it is too late to save yourself"

You are a Shadowblade, capable of crafting the raw stuff of the night into a deadly weapon. At your command, the shadows twist and sway. With a gesture, you can craft a shadowblade, a weapon of pure darkness that is as sharp as any blade of steel. As long as a shadow is near you, you are never unarmed. With your shadowblade, you can slice the raw stuff of a foe’s shadow. With each cut, you extract part of that essence, and at a foe’s death you can infuse that shadow with a magical effect. At your command, the shadows you have harvested appear as looming shades to distract a foe, swirl around you to shield you from sight, or reach forth like hungry apparitions to douse torches and lanterns.

Alignment: Any
Hit Points
Hit Dice: 1d8 per Shadowblade level
Hit Points at 1st Level: 8 + your Constitution modifier
Hit Points at Higher Levels: 1d8 (or 5) + your Constitution modifier per Shadowblade level after 1st

Proficiencies
Armour: Light and shields.
Weapon: Simple Weapons, all one handed swords, light crossbow.
Tools: Thieves Tools
Saving Throws: Dexterity, Constitution
Skills: Choose three from Acrobatics, Arcana, Athletics, Deception, Insight, Perception, Stealth or Sleight of Hand.

Equipment
You start with the following equipment, in addition to the equipment granted by your background:
(a) a longsword or (b) a rapier
(a) a light crossbow and 20 bolts or (b) a shortsword
(a) a burglar’s pack, (b) a dungeoneer’s pack, or (c) an explorer’s pack
Leather armor, two daggers, and thieves’ tools


Shade Form: At 1^st level, you gain the shade form power. When you gave part of your soul to the Shadowfell, the power of that dark realm fused with your material form. As a result, you can assume a shadowy form that allows you to pass through barriers and evade enemies that you could not normally avoid.
When you adopt this form, you blur, your skin becomes gray, and all the gear you carry and the clothes you wear adopt similarly dull colors. Your eyes lose their pupils, becoming blank, white orbs. You cannot damage your foes without returning to your normal form, which prevents you from doing more than maneuvering in for the kill against your enemies.
As a bonus action, you assume a shadowy form that lasts until you make an attack roll or until the end of your next turn. While in this form, you are insubstantial, any attacks against you are at Disadvantage, you can move through people or objects as if they were difficult terrain, and you gain vulnerability to radiant. If you end your turn in a solid object, take 1D10 damage and you are shunted off to the nearest unoccupied space.
As a Bonus action, you can maintain Shade Form.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Shadow Step: Starting at 1^st level, you gain the shadow step power. The shadow energy surrounding every creature touches the Shadowfell slightly, for the realm of death is a creature’s eventual destination. You have the ability to walk the shadow pathways from one creature to another.
Instead of a Move Action, if you are adjacent to a creature, you can teleport up to 20 feet adjacent to another creature.

Shadow’s Shroud: Beginning at 1^st level, you gain the Shadow's Shroud power. The dark magic of the Shadowfell courses through your veins, tainting your soul but granting you the ability to subject an enemy to invisible shrouds that reveal its weakest points. The more of your shrouds there are on a target, the deadlier a blow you can strike against it.
As a Bonus Action, you subject the target to your shroud. If any of your shrouds are already on the target, you subject it to an additional shroud, up to a maximum of four. The shrouds last until you use this power against a different enemy or until the end of the encounter. Before you make an attack roll against the target, you choose to invoke either all your shrouds on it or none of them. If you invoke your shrouds, the attack deals 1d6 damage per shroud, minus one shroud if the attack misses, and all your shrouds then vanish from the target. This damage roll never benefits from bonuses to damage rolls, and is in addition to the attack’s damage, if any.
Executioners Noose: At 2^nd level, you gain the ability to gather shadows into the form of a noose, cast it around your foe’s neck, and pull.
You target one creature up to 30 feet away and make a melee attack. If the attack is successful they take 1D6+dexterity damage. If the target is Large or smaller, you pull the creature up to 10 feet closer to you. This abilities damage increases by 1d6 when you reach 5th level (2d6), 11th level (3d6), and 17th level (4d6).

Cloak of Shades: Beginning at 2^nd level, while you are in dim light or darkness you can take the Hide action as a bonus action.

Haunting Shade: Starting at 3^rd level, more of your essence has bonded with the Shadowfell, making you more at home in the dark places of the world. You gain a +2 bonus to stealth checks and if you don’t already have it, gain darkvision out to 30 feet.

Shadow Darts: At 3^rd level, you launch a volley of chilling darts of shadow energy at your foe. Make three ranged attack rolls. If any of them hit, resolve them as a single hit, and all of them must miss for the attack to miss. 1d8 cold damage if one of the attack rolls hits, 2d8 cold damage if two hit, or 3d8 cold damage if three hit.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Weapon of the Night: Staring at 4^th level, as a bonus action, you can create a shadowblade. It is a one handed blade with the light thrown property, 1d8 +1 (+2 at 9^th level, +3 at 15^th level) piercing damage. The blade count as magical for the purpose of overcoming resistance and immunity to nonmagical attacks and damage. The shadowblade disappears if you are not touching it at the end of your turn.

Master of Shadows: Beginning at 4^th level, when you reduce any enemy to 0 hit points with your shadowblade, you gain a Gloom Shard. As a bonus action, you can expend a Gloom Shard to gain one of the following effects.

• You gain advantage on a single attack against an adjacent enemy until the end of your turn.
• You gain a +5 bonus to the next Stealth check you make this turn.
• You douse a light source until the end of your next turn. The light source must be within 10 squares of you and must be no larger than a lantern.
• Refresh a power that would normally take a short or long rest to refresh.

You can have up to five Gloom Shards at a time.
After a long rest, your unexpended gloom shards vanish, but you gain a Gloom Shard.

Extra Attack: Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn. The number of attacks increases to three when you reach 11th level in this class and to four when you reach 20th level in this class.

Shadowy Escape: Starting at 6th level, you can vanish into the shadows in response to harm. When you take damage, you can use your reaction to turn invisible and teleport up to 30 feet to an unoccupied space you can see. You remain invisible until the start of your next turn or until you attack or cast a spell.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Twilight Assassin: At 7^th level, your shadow leaps from you to attack your enemies, and the two of you fight as one.
You conjure a shadowy duplicate of yourself in an unoccupied square adjacent to the primary target. The duplicate occupies its space, and it lasts until the end of the encounter. Whenever you use a move action, you can also move the duplicate 30 feet. While the duplicate is adjacent to a target, you gain Advantage on attack rolls against it. As a bonus action, until the duplicate vanishes, it can make a regular melee attack against an adjacent target. If it hits, it does 3 points of damage, or 6 damage if the target is currently targeted by a shroud.
The duplicate can be targeted by attack, has an AC of 10+Dex bonus, and has half your hit points.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Bound by Shadow: Staring at 10^th level, as your weapon pierces your foe, you send deadly shadow energy coursing into it, linking your two fates. When you make a successful attack against an enemy, you can expend a Gloom Shard to activate the ability. When you are harmed, so is your foe. Until the end of the encounter, the target takes 5 damage whenever an enemy, including the target, deals damage to you.

Promise of Retribution: At level 13, when a foe attacks you, shadows spirit you away, and you take a small part of the foe’s being with you. You can use your reaction to teleport up to 50 feet away. Once before the end of the encounter, you can use a move action to teleport adjacent to the target. When you do so, you gain a +2 attack bonus against the target and a +5 bonus to damage rolls against it until the end of your turn.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Well of Shades: Starting at 14th level, when you hit a creature with an attack, you can use this feature to instantly transport the target down a well of impenetrable darkness. The creature disappears and plunges down an inky black vortex through the Shadowfell.
At the end of your next turn, the target returns to the space it previously occupied, or the nearest unoccupied space. If the target is not an undead, it takes 10d10 necrotic damage as it reels from its decaying experience.
Once you use this feature, you can’t use it again until you finish a short or long rest.

Veil of Unsight: Beginning at 17^th level, you call shadows to swirl around your target, making you or an ally invisible until the end of your next turn.

Shadow Curse: At level 18, you utter a dark curse upon your foe as you strike it. At your bidding, the shadows you have carved from your enemies leap on that foe like rabid dogs. Until the end of the encounter, you can expend a gloom shard once per turn as a bonus action to deal 10 + your
Dexterity modifier necrotic damage to the target and gain combat advantage against it until the end of your turn.

As much as I do like the fluff from this old class, porting it over almost word for word is way too powerful. To be honest, I don't even need to read past the 1st level features to see that it's quite overpowered. You, essentially, get an almost useless version of sneak attack (sacrificing your turn to add a d6 to an attack is just strictly worse than rogue's sneak attack; its why the class was kind of bad in 4e, and why they tried to redo it with the Executioner assassin); then you add to it a slightly less useful version of the Shadow monk's 6th level feature--at 1st level.

What would I suggest?

Actually, Way of the Shadow monk fits perfectly; get magic initiate for warlock, and get Hex as your first level spell. By the time you get to 6th level, you have all the features that the O-Assassin had, you just have to refluff a tad to keep the flavor. Hex counts as your 'shrouds', and are indeed more powerful, since the extra damage applies to every attack you make while you maintain your concentration (you'll be a little MAD, honestly, because you'll need the Con save to be decently high).

Another option is to go Assassin Rogue, because they're super effective when it comes to the thing that Assassin's tend to do--assassinate people. They're awesome at it.