Con Artist

You have spent a lifetime learning the inns and outs of the criminal underbelly. However, instead of risking your handsomeness and swave charm in the dangerous game of an assassin or the lowly footprint of thieves, you find that your skills are much more tailored to the art of the con.

The Conman's life is a life of high risk and high reward. If you're not ready for things to get a little dicey, and frankly, a little silly, maybe stick to stabbin'!

(PS. This was built for a Pen & Paper game and may not be properly optimized for D&D Beyond.)

The Long Con

You know when one domino falls into place, the sheep always follow. Or, is that how the saying goes?

Starting at 3rd level, whenever you roll multiple Charisma checks in a row, you gain a growing bonus. If you roll 2 charisma checks in a row, you add +1 to your second. On your third, you add +2. On your fourth, +3. The counter stops at the 4th roll in a row, with a maximum of +3.

This bonus resets when you fail a charisma check, make a non-charisma check, enter combat, or take a rest.

At 9th level, the counter stops at the 6th roll, with a maximum of +5.

Luck of the Draw

In this life, you gotta make tough choices. But you also gotta make awesome choices! but you also gotta make choices that keep you alive. But you also gotta make choices that keep you rich! but you also--

At 3rd level: If you roll a natural 20 on an attack roll, you can choose to instantly deal the maximum damage of your critical hit (Any added dice, such as sneak attack dice, become the maximum damage as well). Once you use this ability, you cannot take reactions until the start of your next turn. You can use this ability twice per long rest at third level.

You can use this ability thrice per long rest at 9th level, and 4 times per long rest at 15th level.

Sticky Fingers

Steal all the time. Steal whenever you can. Steal as much as you can!

At 9th level, upon rolling a natural 20 on a non-charisma skill check, you can choose to turn it into a 15 and steal or find something out of sheer luck. The Dungeon Master comes up with a small item or trinket worth at least 1 GP whenever this ability is used.

Some examples of found objects in different scenarios could be:

• While making a Survival check to track an animal, you find a tiny trail of footsteps of unknown origin that lead you to a lost druid's staff.
• While making an Acrobatics check to jump from roof to roof, you find a wedding ring in a crow's nest.
• While making an Insight check to decide whether or not someone is lying, your eye is drawn to something poking out of their pocket. They don't notice when it falls out.
• While making an Athletics check to kick open a door, a small locket falls off the top of the door frame.
• While making a Religion check to learn the significance of a particular statute, you find a note in thieves' cant telling you to push in a particular stone. A secret chamber is revealed with a scroll inside.
• While making a Medicine check to remove the thorn from a lion's paw, it goes over to it's nest and gives you a ornate dagger in return.

And so on.

Golden Handcuffs

Am I trapped in here with you, or are you trapped in here with me?

At 13th level, When taking psychic damage, you can use a reaction to inflict half of the damage you take onto the enemy who dealt it. You can use this twice per long rest.

The House Always Wins

We hold all the cards. Do not fight us in our own game.

Starting at 17th level, you become immune to being charmed or frightened, and gain resistance to psychic damage.