Base Class: Bard
Bards of the College of Games are the master gamblers of the Shivering Isles. Whether running high-stakes casinos in the gaudy palaces of Butcher's Bay or card sharking in the dingy watering holes of Flotsam, these bards use their gifts of card counting and quick wits to dazzle, delight and profit. Accustomed to a life of risks, bards of the College of Games are often thrill seekers willing to put it all on the line for a big payout — going as far as developing their magical talents to push the very brink of what's possible (or wise).
The loyalty of these bards lies in the pursuit of wealth, power and the rush of beating the odds, not in fealty to a monarch or following the tenets of a deity. A pirate lord who keeps such a bard as a herald or advisor knows that the bard fills their de facto court only to further their own goals.
The college's members gather in bars, casinos and sometimes in actual colleges, complete with classrooms and dormitories, to share their magical secrets and business savvy with one another.
Stacking the Deck
When you join the College of Games at 3rd level, your ability to gamble becomes unparalleled.
Bonus Proficiencies: You gain proficiency with dice sets, playing card sets and sleight of hand.
Gambler's Luck: You have advantage on ability checks to use dice sets, playing card sets or sleight of hand ability checks to manipulate a game.
Bookmaker
Also at 3rd level, you learn how to intertwine your sharp wit and magical talent to tip the odds in your favor.
Flash at Closing Line: When a creature that you can see within 60 feet of you succeeds at an attack roll, damage roll or an ability check, you can use your reaction to expend one of your uses of Bardic Inspiration. Roll your Bardic Inspiration twice. If the two rolls are both even or odd numbers, then subtract the higher total from the creature's roll. If one of the rolls is even and the other is odd, then the Bardic Inspiration fails and you add nothing to the ability check. The creature is immune if it can't hear you or if it's immune to being charmed.
Chalk Player: When you make an ability check, you can expend one use of Bardic Inspiration. Roll your Bardic Inspiration twice. If the two rolls are both even or odd numbers, then add the higher total to your ability check. If one of the rolls is even and the other is odd, then the Bardic Inspiration fails and you add nothing to the ability check.
Against the Spread
At 6th level, your ability to bend reality for the better and the worse grows. Your Bardic Inspiration becomes equally powerful and unpredictable, allowing you to perform amazing feats and horrible failures.
Double Down: Whenever you use Flash at Closing Line or Chalk Player, you can now double down for additional benefits. If the two Bardic Inspiration rolls are both even or odd numbers when engaging in Flash at Closing Line or Chalk Player, you can now opt to take your winnings and allow the abilities to play out as normal or reroll the two die. If you choose to reroll the two die, first declare if the roll values will both be even or odd. If your declaration proves correct, the Bardic Inspiration is successful and you may apply the sum of all four rolls to the targeted creature. If your declaration is incorrect, then nothing happens and you lose two uses of your Bardic Inspiration.
Hot Hand: Every time you succeed at Flash at Closing Line or Chalk Player, gain a Hot Hand chip. Double Down successes are each worth three Hot Hand chips. At five Hot Hand chips, you can use a bonus action to Cash In. Your total Hot Hand chips resets to zero after a long rest.
Cash In: Give yourself advantage on all ability checks, saving throws and attack rolls for one minute. You can not gain Hot Hand chips while Cash In is active.
Dog Player
Starting at 14th level, your ability to tilt fate is as powerful as it is addicting. While still unpredictable, your magical gambles always end spectacularly.
Upping the Ante: You no longer lose your Hot Hand chips after a long rest. Double Down successes are now worth five Hot Hand chips each. Every time you enter combat, gain one Hot Hand chip.
Jackpot: At 10 Hot Hand chips, you can use a bonus action to claim a Jackpot. Claiming a Jackpot gives a number of creatures within 60 feet of you who can hear you, equal to a roll of your Bardic Inspiration die, disadvantage on saving throws against your spells for one minute.
All In: As a bonus action, you can use all of your bardic power for one magnificent moment. Declare if a majority of the dice will roll even or odd values, then roll all of your available Bardic Inspiration. If your declaration is correct, then you may add the sum of all the dice to your, or a willing creature within 60 feet of you who can hear you, next ability check, attack roll, damage roll or saving throw within the next hour. Alternatively, you may subtract the total from one target's ability check, attack roll, damage roll or saving throw within the next hour if they are within 60 feet of you and can hear you. If your declaration is incorrect, you instead lose all uses of your Bardic Inspiration and are stunned for one round.