High Roller

After a misguided youth spent in dank taverns and crappy casinos, you've mastered the ability to lie, bluff, and scam your way out of most situations. If that doesn't work, then you are an expert at stacking the deck in your favor. High Rollers are generally misunderstood by those unfamiliar with the nuance of crime. What outsiders perceive as blind luck is actually days or weeks of meticulous planning and incredible detail, combined with a healthy dose of blind luck. All rogues are skilled in getting their own way, but it's the trademark of the High Roller to have your mark still smiling at the end.

Poker Face

At 3rd level, you gain proficiency in Deception if you did not already have it. Make all Deception checks with advantage.

Five of a Kind

Beginning at 3rd level, your Slight of Hand becomes legendary. Slight of Hand checks that aren't made with disadvantage automatically succeed. Slight of Hand checks that would normally be made with disadvantage (clothes people are wearing, items people are holding, etc.) are rolled straight.

Additionally, you learn the Mage Hand cantrip.

Bluff

At 9th level, your lies get bigger and more elaborate. When someone makes an attack against you, you can use your reaction to make an opposed Deception check against your enemy's Insight. On a success, you can pretend that the blow killed you outright, prompting your enemy to move on from attacking you (regardless of whether or not the attack hit). The next attack you make is made with advantage.

Ace in the Hole

By 13th level, your understanding of the ebb and flow of battle allows you to predict how combat will go with incredible precision. As an action, pick a target and make an opposed Intelligence check against their Insight. On a success, the target releases a Trap you set up during or before combat. On a failure, the target evades the Trap. You do not need to take an action beforehand to prepare the Trap, but you will need to obtain the materials for the Trap before using Ace in the Hole. Whether or not your trap succeeds, the materials of the Trap are used up. The four Traps you can make are Mine Traps, Acid Traps, Poisoned Needle Traps, and Snare Traps.

Mine Traps explode when activated. Cost: 60 gp. Damage: 3d10 fire.

Acid Traps shatter when activated. Cost: 60 gp. Damage: 3d10 acid.

Poisoned Needle Traps shoot a dart when activated. Cost: 60 gp. Damage: 3d10 poison.

Snare Traps scoop up humanoids when activated, making them restrained. Cost: 20 gp.

The House Always Wins

When you reach 17th level, your planning becomes impossibly intricate. After completing a long rest, make a DC 30 Charisma check (Persuasion or Deception). On a success, you have successfully prepared a long con on a target you're already aware of. During an encounter with them, use an action to make that plan come to fruition. Examples could be bringing an army or a battalion of guards to combat, making an important ally of theirs turn on them, or making an elaborate cage to trap them in. Once you've made the DC 30 Charisma check, stop rolling them until you've used the action. Once you've used the action, begin rolling Charisma checks again.