“Jack” was a stock hero in Cornish and English mythology, famous from such stories as Jack the Giant Killer and Jack and the Beanstalk. He was typically portrayed as a young man, unconcerned with values like hard work, and sharing many qualities with tricksters such as Loki and Reynard the Fox. He is characterized by his bravery and guile, his wits (despite a lack of wisdom), and often by his surprising strength, speed, and luck. This underdog hero has influenced almost every portrayal of a cunning youth in western stories, and so we found it appropriate to adapt as a Rogue archetype for 5th edition. While creating it, I referred to the archetype as “Jack,” but you could use the name of another stock character suited to your campaign setting, or simply “The Trickster.”
You rely on your self-confidence and your way with words to win the day against superior foes; luring them into traps, tricking them into brawls with one another, or simply scaring them away. If all else fails, you are more than a little lucky, and you don’t hesitate to finish a foe with a timely blow.
Bluff and Bluster
When you select this archetype at 3rd level, If you are proficient in Charisma (Intimidate) checks, you are also considered proficient in Charisma (Deception) checks, and vice versa.
When you make a Charisma (Intimidate) check, your result also counts as a Charisma (Deception) check if it includes a lie or exaggeration. A creature who fails an opposed Wisdom (Insight) check is simultaneously intimidated and deceived.
When you make a Charisma (Intimidate) or a Charisma (Deception) check, you use the total of your check or 8 + your Charisma modifier, whichever is higher. If you are proficient in Intimidate and Deception, you add your proficiency bonus to the fixed result. If you chose Intimidate or Deception as a skill augmented by your Expertise feature, add double your proficiency bonus.
Bold beyond Reason
Beginning at 3rd level, you have advantage on saving throws vs. being frightened. If you have the Brave racial trait, you gain +1 to such saving throws as well.
Better Lucky than Good
When you reach 3rd level, you gain one luck point. You may spend this luck point to roll an additional d20 for any ability check, attack roll, or saving throw made by you, an ally, or an enemy creature you are aware of, then you choose which d20 result is used. You must declare the use of this point before the results of the roll are known. If multiple creatures spend luck points to influence a roll, they cancel each other out, no additional dice are rolled. You regain any expended luck points after completing a long rest (If you are using feats, this point stacks with and works identically to those gained from the Lucky feat).
Starting at 9th level, as an action, you can choose a number of creatures equal to your Charisma modifier that can see or hear you and begin to boast at them, telling them of your fearsome reputation, the consequences of crossing you, gossip you heard about the creatures and their weaknesses and failings, or whatever you find appropriate to the situation.
If those creatures can understand your language, they must make a Wisdom saving throw vs. 8 + your proficiency bonus + your Charisma modifier. If they fail, they are either frightened of you or charmed by you (your choice, you must choose the same result for all targets) for 1 minute. This effect ends immediately if you or your allies attack any of the creatures.
While creatures are frightened this way, as an action, you may may make a Deception check against a DC of 10 + the creatures’ CR + the creatures’ Wisdom modifier (use the highest among all creatures) to cause them to flee the immediate area (the frightened effect still ends after 1 minute)
While creatures are charmed this way, as an action, you may may make a Deception check against a DC of 10+ the creatures’ CR + the creatures’ Wisdom modifier (use the highest among all creatures) to make them fight other creatures they are naturally inclined to dislike (such as causing two rival hill giants to brawl for superiority). The charm effect ends if any of the creatures drops to 0 HP (or after 1 minute, whichever comes first).
At 13th level, you gain an additional luck point. When you roll Sneak Attack damage, you may expend a luck point to reroll all of your damage dice and use the highest total.
Fell the Unwitting
Beginning at 17th level, the effects of your Convincing Boast no longer end immediately if an affected creature is attacked by you or an ally; instead the creature gets a new saving throw against the effect with advantage. When you make a sneak attack against a creature that is charmed or frightened, you add 2d6 to the sneak attack dice.