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Subclass Rogue Assassin
The Assassin is a Rogue subclass built around Initiative, ambush, and disguise. Assassinate at Level 3 grants two simultaneous benefits: Advantage on Initiative rolls (+5 Initiative bonus) and massive bonus damage on the first round against creatures that haven't acted yet. Assassin's Tools provides Disguise Self and a Poisoner's Kit. Roving Aim at Level 9 removes the movement restriction from Steady Aim — you can have Advantage on your attack and still move freely.
| LEVEL | FEATURE |
|---|---|
| 3 | Assassinate, Assassin's Tools |
| 9 | Roving Aim |
Assassinate: Initiative You have Advantage on Initiative rolls. Additionally, you gain a +5 bonus to your Initiative.
Assassinate: Surprising Strikes During the first round of each combat, you have Advantage on attack rolls against any creature that hasn't taken a turn. If your Sneak Attack hits any target during that round, the target takes extra damage of the weapon's type equal to your Rogue level.
Assassin's Tools You gain a Disguise Kit and a Poisoner's Kit, and you have proficiency with them. You can cast Disguise Self and use the Poisoner's Kit from your action bar.
Roving Aim Your Speed isn't reduced to 0 by using Steady Aim. You can move freely on turns when you activate Steady Aim.
The Assassin is the first-strike burst damage Rogue subclass. Assassinate: Initiative gives +5 to Initiative rolls plus Advantage — at 20 Dexterity (+5), an Assassin rolls d20+10 with Advantage for Initiative. This almost guarantees acting before any enemy on Turn 1.
Assassinate: Surprising Strikes is the payoff: on Turn 1, you have Advantage on every attack against a creature that hasn't acted. Any Sneak Attack hit during that round deals an additional Rogue-level bonus damage (weapon type). At Level 9, that's +9 damage on top of Sneak Attack dice.
The Turn 1 sequence: Act first (Advantage + Initiative bonus) → Hidden from setup → Attack with Advantage (Stealth guarantees Sneak Attack conditions) → Sneak Attack + bonus damage → potentially drop a target before it acts.
Roving Aim at Level 9 removes the last downside of the Assassin's core toolkit. Steady Aim normally pins you in place — valuable for guaranteed Advantage, but creates an obvious kill target. Roving Aim lets you use Steady Aim, take the attack, and still move to cover using Cunning Action: Dash or Disengage.
Assassin's Tools supports non-combat applications: Disguise Self for infiltration, Poisoner's Kit for coating weapons with contact poison before encounters.
Rogue, Arcane Trickster, Assassin, Highway Rider, Scion of the Three, Soulknife, Swashbuckler, Thief