College of Scoundrels

Known for their exuberant lifestyles, Bards often lose their way to the pursuit of drink, coin, and lovers. Those Bards who fall from grace, as well as those who never made it in the first place have a choice, resign to a life of destitution or embrace the chaos of a life on the edge. Those that do embrace it are affectionately dubbed the College of Scoundrels, doomed for life to pursue only the greatest heights upon the precipice of the most perilous falls. These Bards value chaos and risk above all else, always hoping to get one up on others, whether those be a stranger at a card table or a fearsome dragon with a weighty horde. The only thing truly known to cause a College of Scoundrels Bard to turn tail and run is the consequences of their own actions. 

 

Con Artist

When you join the College of Scoundrels at 3rd level, you gain proficiency with the Sleight of Hand if you haven't already. In addition, you gain proficiency in two gaming sets. 

Coin of Fate

At 3rd level you learn to push your luck to a knifes edge, and put your fate into the hands of a single coin flip. When you roll a d20 for an ability check, saving throw or attack roll you may expend a use of bardic inspiration. When you do so, before you roll you can instead elect to flip a coin, calling it before you do so. (Or conversely split the d20 into odds and evens, again calling the result before you roll). If you are successful the result immediately becomes a critical success, or a 20 if criticals do not apply. Otherwise the result becomes an instant critical failure or a 1. This ability cannot be used in conjunction with advantage or disadvantage, if your roll has advantage/disadvantage you must use this feature before you roll any of the dice and you only flip once, abiding by that result.

Coin of Fate 2

At level 6 you learn to put everything into an attack or spell. You can now use your Coin of Fate feature on damage rolls also. In this case before rolling any damage dice you may expend a bardic inspiration use to flip a single coin instead. A success means the attack or spell does max damage, however a failure results in the attack missing, dealing no damage whatsoever. 

Let's make this interesting...

Now at 6th level you seek ways to up the stakes even further. You always have advantage on persuasion roles that involve proposing or modifying wagers.

Tweaking the Odds

At 6th level you have learnt to tweak the threads of fate to take full advantage of missed opportunities, but at a cost. Roll 2 d20. If either are a 20 or 1 or are duplicates of each other reroll until you have two different numbers that aren't 20 or 1. Pick one of these numbers, every time you roll this number for an attack roll, you can treat this number as a natural 20, however the other number shall always be a natural 1 in the same situation.

Deck of Gambles

At level 14 your flirtation with the fates captures the attention of otherworldy eyes. Upon gaining this level a mysterious entity of chaos from another plane leaves you a weathered leather pouch in your sleep. Inside is a Deck of Gambling, this deck of 14 cards can only be used by you, they become inert magically in anyone elses hands, appearing to be just a plain set of playing cards with intricate designs. The details of the deck are as follows:

Deck of Gambles:
Adventuring Gear, Wonderous Item

A pouch containing 14 magical cards. As an action you can draw a single card from the deck at random, activating its magical effect and causing the card to dissapear forever. Each card in the deck corrisponds to a particular effect which occurs instantaniously. The effects are indicated below.

Ace	Gender Swap - You instantaneously become the opposite sex to what you were at the time.
2	Teleportation - Roll a d6. You instantaneously teleport 1000ft in the direction determined by the dice roll. If you teleport into a solid object you will not be crushed but will begin suffocating. 1-North 2-East 3-South 4-West 5-Upwards 6-Downwards
3	Power Up - As of the moment of drawing the card you are filled with vibrant potential. This potential is lost if you are hurt at any degree. If you take 0 damage in the next 24 hours you instantly gain another level.
4	Touch of Death - Your soul has been touched by death and weakened. Next time you reach 0 hp and fall unconscious you immediately begin with two death saving throw failures.
5	Horn of the Immortal Knight - You receive an ancient bone horn that can be blown at any time. As a bonus action you can blow the horn, destroying it in the process but immediately bringing to your aide an undying knight who pledges complete fealty to you, honoured to fight for you.
6	Allergy - You instantaneously develop a deathly allergy to a random trigger (At the DM's Discretion). This allergy is highly potent and causes anaphylaxis merely to the touch. You lose access to air the moment you come into contact with the allergen.
7	Ability Increase - Roll a d6. You gain a permanent increase in a random stat corresponding to the dice roll: 1-Strength 2-Dexterity 3-Constitution 4-Intelligence 5-Wisdom 6-Charisma
8	Brain Swap - Roll a d20. The result is now your base intelligence score.
9	Riches! - Gemstones of various cuts cascade from the air around you. They amount to the equivalent worth of 1000 x1d4 gp.
10	Curse - The card curses you. You take a -2 penalty on Saving Throws while Cursed in this way. Only a god can end this curse.
Jack	Haste - You gain the once per long rest ability to cast haste on yourself at will as an action. It costs nothing and is not subject to concentration.
Queen	Dragon's Slumber - A dragon with a challenge rating of at least 20 is released from the card and awakes in a random location in the world (at the DM's discretion). You are aware if its existence and it is aware of yours as the one that released it.
King	Power Word Kill - You gain one limited use of the spell Power Word Kill at no cost. This card gives you one charge, once it is used it cannot be regained.
Joker	Doppelganger - You are instantly transported to an extradimensional space where before you stands a complete copy of you exactly as you are now. However, the copy has an alignment completely opposite to yours and is instantly hostile to you. The winner of the fight is transported immediately back to where you were and becomes you. Any duplicate items carried back with you disappear.