College of Fortune

Bards in the College of Fortune know that if you trust Lady Luck, she will never let you down. These performers travel from town to town, fleecing the locals in whatever casino or gambling institute the local law allows. Amongst their companions, Bards of the College of Fortune are known to walk in an almost palpable halo of good fortune. A good fortune, thankfully, they are willing to share.

This subclass is not my original idea, nor are the features in it created by me. I found it on twitter and really wanted to use it here on D&D Beyond, so I have simply transcribed it here.

Original Creator of Subclass: coolgamertagbro

Bonus Proficiencies

At 3rd level, you gain proficiency in 3 gaming sets and one skill: Deception, Insight, Perception, or Sleight of Hand. Your proficiency bonus is doubled for any ability check you make that uses a gaming set proficiency.

Push Your Luck

Starting at 3rd level, you instill a bit of your gambling confidence in your compatriots when you inspire them. When a creature you inspired rolls a Bardic Inspiration die, they can choose to roll an additional Bardic Inspiration die. If the additional Bardic Inspiration die result is lower than the first,  the roll loses its benefit from Bardic Inspiration and the creature loses the Inspiration die. If the additional Bardic Inspiration die result is equal to or higher than the initial, add the result of both dice to the roll and the creature loses the Inspiration die.

Luck of the Draw

Starting at 6th level, you find mystical power in a deck of cards, capable of invoking its esoteric symbolism when it suits you. When you complete a long rest, draw three random cards by rolling on the chart below.

1-Strength Woe           7- Strength Weal
2-Dexterity Woe          8-Dexterity Weal
3-Constitution Woe    9-Constitution Weal
4-Intelligence Woe     10-Intelligence Weal
5-Wisdom Woe           11-Wisdom Weal
6-Charisma Woe         12-Charisma Weal

You keep each card until you play it or your next long rest. When a creature you can see makes a saving throw, ability check, or attack roll and applies the ability score of a card you drew, you can expend your reaction and play a card that matches the applied ability score. If you play a weal, the creature gains advantage on the roll. If you play a woe, the creature gains disadvantage on the roll. 

Pocket Ace

Starting at 14th level, you gian an additional use of Bardic Inspiration. When you complete a long rest, roll one of your Bardic Inspiration dice and record the result as your Pocket Ace. After a creature you inspired rolls a Bardic Inspiration die but before they choose to use your Push Your Luck feature, you can exchange the results of their Bardic Inspiration die and your Pocket Ace. You must choose to replace the result before the DM announces if the roll succeeds or fails. You can expend your Pocket Ace at any time to add its result to one of your own attack rolls, ability checks, or saving throws.