Gambler

The flip of a coin, the roll of the dice. The chance at pure failure or unrivaled success. The way of the Gambler is that of chance and can be the greatest aid to a combat encounter or the worst kind of detriment. Those who adhere to this archetype take the term "flip of a coin" and take it literally in nearly all aspects of their life, and death. 
The way of a Gambler is to take the very best of your skills and attempt to push your luck to go beyond them. Those who adhere to this archetype tend to be thrill-seekers, adrenaline junkies, and those with little to no impulse control, both on and off the battlefield. 

Take a chance

Starting at 3rd level, you gain a number of Lucky Coins that equal your Rogue level, you can flip one of these coins to perform the following. 

• Before you roll for the damage of your Sneak Attack feature, you can flip a Lucky Coin. Heads causes the damage rolled to be doubled, Tails causes the damage to be halved. 
• Whenever you roll an ability check you can flip a Lucky Coin as long as you do so before success or failure is called by your DM. Heads allows you to double the modifier for that ability, if you have a negative modifier then that is instead treated as a positive with a score equal to your proficiency bonus. Tails causes any positive modifiers to become negative. 

Own Luck

When you choose this archetype at 3rd level you have learned to make your own luck. You gain proficiency in Sleight of Hand, Deception, and Persuasion. Your proficiency bonus is doubled for any ability check you make that uses those proficiencies.

Lucky Shot

At 9th level you can use your reaction to flip one of your Lucky Coins when you are targeted by a ranged or melee attack roll. On Heads, you cause that hit to miss and if another hostile creature is within 5 feet of you, the attack instead targets them. On Tails, the attack hits as normal. 

Lucky Number

Starting at 13th level, you have learned your lucky number. When you gain this feature choose a single number on the d20 other than 1. When you roll that number for Ability Checks (Including Initiative rolls), Attack Rolls and Saving Throws you can treat that number as if you had rolled a 20.

All In

Starting at 17th level, you can double down on your luck. When you flip one of your Lucky Coins and land on heads you can choose to flip another to further increase the effects.

• Take a Chance. When rolling for sneak attack damage and land on Heads a second time, you add an additional 4d6 damage to your sneak attack roll. If used on an Ability Check your roll gains an additional +10.
• Lucky Shot. When you land on heads to avoid an attack roll you can attempt to land on Heads a second time. Doing so allows you to make an attack of your own as part of the same reaction, this attack gains the benefit of your Sneak Attack even if you have already used your Sneak Attack this round.
  
  In addition, when you roll Tails on your Lucky Coin you can choose to roll again in an attempt to land on Heads to negate the effects. 
  
  
• Take a Chance. When you land on Heads to negate the first coin you no longer deal half damage and instead add 1 additional damage die. When you do this for an Ability Check you no longer treat positive modifiers as negative and instead add an additional +2 to the total rolled.
• Lucky Shot. When you land on Heads to negate the first coin you reduce the damage taken by the attack by an amount equal to your Rogue level. 
  
  If you roll Tails when using this feature your first Lucky Coin flip remains as it was.