High Roller
Some rogues rely on shadows; others on their blades, their words, or their magic. High Rollers rely on luck—or at least on the art of making luck believe it has a choice.
A High Roller approaches life like a gambling table: a smile on their lips, a coin between their fingers, a loaded die up their sleeve, and a backup plan behind every wager. They know chance is real, but they also know a true gambler never lets chance play alone.
For these rogues, every strike is a stake, every dodge a wager, every lie a hidden card. They do not merely seek to survive misfortune: they seek to steal it.
Rogue Subclass: High Roller
Fortune Stakes
3rd-level Rogue feature
You learn to give your luck physical form as coins, tokens, marked cards, or loaded dice called Fortune Stakes.
You have a number of Fortune Stakes equal to your proficiency bonus + your Dexterity modifier, with a minimum of 1. You regain all expended Fortune Stakes when you finish a long rest.
Your Fortune Stakes are not actual gold pieces, though you can represent them with real coins, cards, or dice at the table. They represent your daring, your instincts, and your ability to nudge chance in the right direction.
You cannot spend more than one Fortune Stake on the same d20 roll unless a feature of this subclass explicitly says otherwise.
In addition, you gain proficiency with two gaming sets of your choice, such as dice, playing cards, dragonchess, or Three-Dragon Ante.
Blade's Wager
3rd-level Rogue feature
When your blade finds an opening, you can stake your luck on an impossible strike.
Once per turn, when you hit a creature with an attack using a finesse weapon or a ranged weapon, and that attack can benefit from your Sneak Attack, you can spend 1 Fortune Stake to make a wager.
Choose heads or tails, then flip a coin. You can also roll any die: an even result counts as tails, and an odd result counts as heads.
If you win the wager, the attack deals extra damage based on your Rogue level, as shown in the table below.
| Rogue Level | Extra Damage |
|---|---|
| 3rd | 1d6 |
| 9th | 2d6 |
| 13th | 3d6 |
| 17th | 4d6 |
If you lose the wager, the attack deals its normal damage, but luck briefly turns against you: you cannot take reactions until the start of your next turn.
Double or Nothing
9th-level Rogue feature
Your luck does more than protect you when you strike: sometimes it saves you at the last instant, when an enemy's blade should already have found its mark.
When you use Uncanny Dodge to reduce the damage of an attack that hits you, you can spend 1 Fortune Stake to turn that dodge into a wager.
The creature that hit you chooses heads or tails. Then flip a coin. You can also roll any die: an even result counts as tails, and an odd result counts as heads.
If the creature loses the wager, you take only one-quarter of the attack's total damage, instead of half.
If the creature wins the wager, your Uncanny Dodge works normally: you take only half of the attack's damage.
Cheating Fate
When the creature wins this wager, you can try to rig the result at the last instant by sacrificing some of your personal wealth.
To do so, you must spend a number of gold pieces equal to:
5 × your Rogue level × your proficiency bonus × the number of times you have used Cheating Fate since your last long rest, including this use.
If you pay this cost, you turn your loss into a win: you take only one-quarter of the attack's total damage.
Gold pieces spent this way are lost. They might be tossed away, broken, blackened by ill luck, offered to fate, or simply vanish amid the impossible coincidences that surround your art. They cannot be recovered.
You must own or carry enough personal wealth when you use this feature. If you do not have enough gold available on your person, you cannot cheat fate. Deliberately carrying less gold never reduces this feature's cost: it simply prevents you from using it.
Impossible Dice
13th-level Rogue feature
You have learned to roll dice that should not exist: dice with twenty-one sides, twenty-two sides, or perhaps just ordinary dice no one has ever managed to read correctly.
When you flip a coin for a feature of this subclass, you can flip two coins instead of one and choose whichever result you prefer.
In addition, when you make an attack roll, ability check, or saving throw, you can spend 1 Fortune Stake after seeing the d20 roll, but before the DM announces whether the roll succeeds or fails.
Roll 1d4 and apply the following result to the roll:
| d4 | Effect |
|---|---|
| 1 | Subtract 2 from the roll. |
| 2 | Subtract 1 from the roll. |
| 3 | Add 1 to the roll. |
| 4 | Add 2 to the roll. |
This modifier can turn a failure into a success or a success into a failure.
If you use this feature on an attack roll, it cannot turn a natural 1 into an automatic success or turn any other result into a natural 20. It modifies only the roll's total.
Jackpot
17th-level Rogue feature
You know the perfect moment: when the world holds its breath, the coin spins in the air, and fate waits to learn who truly holds the cards.
When you hit a creature with an attack using a finesse weapon or a ranged weapon, and that attack can benefit from your Sneak Attack, you can declare a Jackpot. You must do so before rolling damage.
When you declare a Jackpot, spend 2 Fortune Stakes, then flip a coin. Thanks to Impossible Dice, you flip two coins and choose whichever result you prefer.
If you win the wager, the attack becomes a critical hit.
If you lose the wager, the attack deals only half of its total damage, after all dice have been rolled and all modifiers applied.
You cannot use Blade's Wager and Jackpot on the same attack.
