The Rounder

While most rogues rely on meticulous planning or practiced muscle memory, the Rounder treats every encounter—from a high-stakes heist to a life-or-death brawl—as a game to be played and won. Rounders are never just reckless; they are masters of calculated chaos who know how to manipulate situations, read the room, and cheat the hands of fate in their favor.
Rounders turn probability into a game of resources. They thrive in unpredictability, often using dice, cards, or flipped coins to dictate their combat tactics. If they think that there are no other options to win, Rounders simply force an opponent into a devastating misstep. These rogues thrive on the high stakes and random thrill of the game of life. They rarely play fair, employing sleight of hand, misdirection, and subtle tricks designed to tip the odds in their favor.
Cool under pressure, these rogues possess an unshakeable nerve. A kind of bravado that would rival a trouble-making bard. They prefer a situation of chaotic SNAFU; and actively provoking such situations because they know they react faster to sudden shifts in momentum than anyone else.

Card Shark

Starting at level 3, your wily personality paired your agile movements frequently draws unwanted attention from unsavory individuals, prompting you to learn how to turn anything within your reach into a weapon.

You learn the following.
Improvised Finesse and Thrown Property. Improvised Weapons you use gain the Finesse and Thrown(20/60 ft.) properties.

Improvised Weapon Proficiency. You have proficiency with Improvised Weapons.

Playing Card Proficiency. You have proficiency with Playing Cards.

Fortune of the Bold

Also at level 3, you always trusts the Fates to guide your hand. Attacks you make are due to luck instead of precision. Whenever you deal Sneak Attack damage, you can roll a 1d10. You can use this feature a number of times equal to your Proficiency Bonus, and you regain all expended uses when you finish a Long Rest.

Roll D10 — Effect

On a 1 — The total number of Sneak Attack dice is doubled and become d8's for this attack.
On a 2 to 5 — Add an additional [roll]3d6[/roll] Sneak Attack dice for this attack.
On a 6 to 10 — The number of Sneak Attack dice is halved (rounded down, minimum of 1 die). 

Situational Awareness

At level 9, your experience sharpened your awareness to the first signs of trouble.

Your experience grants you these benefits.
Attentive. You have Advantage on Wisdom (Insight) and Wisdom (Perception) checks.

Initiative Bonus. You gain a +5 bonus to Initiative rolls.

Smooth Talker. When you make a D20 Test as part of the Influence action targeting a creature with which you share a language, you have Advantage on the check.

Faro Luck

At level 13, you have mastered certain tricks and chicaneries that somehow trick the Fates into granting you good fortune. Whenever you use your Fortune of the Bold feature, you may roll 2d10 and choose which die to use.

Swagger like a Boss

Beginning at level 17, you can slip away unnoticed from those who try to harm you, making you hard to catch.

You gain these benefits.
Elbowroom. Difficult Terrain doesn't cost you extra movement, and spells and other magical effects can neither reduce your Speed.

Feint & Fade. Whenever you use your Uncanny Dodge feature, you can immediately move up to half your Speed. This movement doesn't provoke Opportunity Attacks.

Nerves of Steel. You have Advantage on ability checks and saving throws to avoid or end the Charmed, Grappled, Paralyzed, and Restrained conditions on yourself.