Betting Man

You have honed your skills around the poker table, or huddled in alleyways filled with the sounds of the clattering of dice. Carousers, gamblers, and superstitious fools follow this archetype, as do those who can't help themselves when it comes to friendly wagers, and to those who know that the sweetest victories are those which come with the highest risks. In addition to altering your activities with luck, you learn the ploys needed to ply information from others and to make your most vicious blows all the more powerful, every reward at the risk of losing it all.

Superstitious

Starting at 3rd level, your superstitions begin to influence your life in positive and negative ways. When you finish a long rest, roll two d20s. If either number is a 1, 20, or if both numbers are the same reroll both d20s until these conditions are met and the record the numbers rolled. The lower of the two numbers becomes your lucky number, while the higher of the two becomes your unlucky number.

Whenever you make an attack roll, ability check, or saving throw and roll your lucky number on the d20, treat it as if you had rolled a natural 20. Whenever you make an attack roll, ability check, or saving throw and roll your unlucky number on the d20, treat it as if you had rolled a natural 1.

When you finish a long rest, reroll your superstition dice.

Gambler

When you choose this archetype at 3rd level, you gain proficiency in all gaming sets.

In addition, select one gaming set to be your favorite game. You gain expertise in that gaming set.

"Friendly" Wager

At 9th level, your penchant for gambling allows you to goad others into disclosing information upon losing a game of chance. When you are playing a game with another creature using your favorite gaming set, you may force your opponent to set stakes for the game. These stakes are determined by the DM, but are influenced by the nature of the creature and their desires, and can include material things such as gold or a specific magic item, or the immeterial such as information or a minor favor. For example a greedy creature such as a goblin may simply want gold, while a creature held captive might wish to be set free. To set and agree to these terms, a creature must have an Intelligence score of at least 5, and you must share a common language.

If you agree to the terms of the wager, you can then make a Charisma (Gaming Set) check contested by either the creature's Wisdom (Insight), Charisma (Deception), or Charisma (Intimidation) check as determined by the DM. On a failure, the creature gains what you wagered.

On a success, you can ask the creature up to five questions which they must answer. Answers can be brief, cryptic, or repetitive, and the creature is under no compulsion to offer a truthful answer if you are hostile to it or it recognizes you as an enemy, though creatures with lawful allignments are more compelled to speak truthfully.

The Old Stand Bys

Starting at 13th level, after you roll your superstition dice, you may instead immediately choose to make 7 your lucky number, and 13 your unlucky number.

Press Your Luck

When you reach 17th level, you can gamble on the outcome of your sweetest victories, at the cost of making them mundane. Whenever you land a critical hit but before resolving your damage, you may call high or low and roll a d20. If the result is 11 or higher, it is high. If the result is 10 or lower, it is low.

If you guess correctly, you may roll all of the attack's damage dice three times instead of twice when resolving damage. If you guessed incorrectly, the attack becomes a normal hit.