The Bastard

Credit goes to u/ejaculatingbees for making this subclass on reddit!

While often looked up with distrust, most rouges are generally acknowledged as skilled and often invaluable members of their respective groups; ones others can trust with their lives. However, the Bastards, as they are colloquially known, are rarely afforded that kind of trust. Marked by their proclivity for constant and blatant underhandedness in every aspect of their work, Bastard rouges are less professionals that use deception as a tool and more compulsive liars and cheats that are good with a blade. They do so with abandon and without shame, striking out brazenly with the same inherent dishonesty they observe in the world around them.

Cheap Tricks

When you choose this archetype at 3rd level, you gain proficiency in the deception and sleight of hand skills, as well as proficiency with one gaming set of your choice. If you were already proficient in deception or sleight of hand, you instead gain expertise.

You also learn either the Minor Illusion, Prestidigitation or Thaumaturgy cantrip. Your spellcasting modifier for it is Charisma. In addition, whenever you use this spell in an attempt to decieve someone, creatures have disadvantage on all checks made to see through this deception

Tripper

Also at 3rd level, you learn to punish your opponents' attempts at retreat with swift and unexpected retaliation.

When a creature of size large or smaller leaves your melee range, you can use your reaction to try and trip them, forcing them to make a dexterity saving throw of DC 8 + your proficiency bonus + your dexterity modifier or fall prone. If they fall prone, you can immediately follow up with a single weapon attack as part of the same reaction before they can get back up. If the creature is huge or larger, you can still attempt to trip them. If you do so however, the saving throw DC uses your strength modifier instead of dexterity.

Elusive Scoundrel

At 9th level, your underhanded activities have required you to hone your evasive maneuvers and escape tactics, ensuring that you may live to swindle another day.

You gain the following benefits when using your cunning action feature:

• When Disengaging as a bonus action, all creatures within 5 feet of you when you take the disengage action have disadvantage on the next attack they make against you before the start of your next turn.

• When Dashing as a bonus action, you can move an additional 10 feet.

• When hiding as a bonus action, you can hide even if the area is only lightly obscured.

Cracks in the Armor

At 13th level, you notice gaps in your opponents's defenses the instant they appear and are able to strike them with the same swiftness.

Whenever a creature within range of one your attacks, melee or ranged, enters a state that would grant you advantage on your attack against them (falling prone, becoming stunned, being hit by a Guiding Bolt etc.), you can use your reaction to make one such attack against them. If your target is within your movement range, you can move up to them before making your attack as part of the same reaction.

One last middle finger

At 17th level, you become capable of making one last decisive strike in the event that you fall in battle, making sure you always get the last laugh.

When you are reduced to 0 hit points by a creature, you can make one weapon attack against it with advantage if it is within range. If the attack lands, it counts as a critical hit and they suffer one of the following effects of your choice:

• Their movement speed is halved for the next minute.
• They have disadvantage on all saving throws until the end of their next turn.
• They have disadvantage on all attack rolls until the end of their next turn.

If the attack reduces the creature to 0 hit points, you regain 1 hit point and rise to your feet in a moment of smug self-satisfaction. Once you use this feature, you cannot use it again until you complete a long rest.