Highroller

The Highroller is a subclass for those who feel as if the odds are always stacked against them and yearn for a more fortuitous experience, for those who like to take risks with the potential to reap great rewards, or maybe just for those who are stuck filling the offensive position in the party who want to be a little bit more than just the token DPS. Regardless of the reason, the Highroller is a subclass based around the idea of having a little bit more control over the dice without completely breaking the game, while still including some elements of risk and reward.

Highrollers are a special breed of fighter, one that relies much more on inborn luck over talent or skill. They combine a healthy amount of risk taking with copious opportunities to put the odds in their favor, allowing them to scrape by seemingly by the skin of their teeth. "Why are they so lucky?", one may wonder. "Have they been favored by some sort of divine being, who influences the world in their favor and has some sort of ulterior motive to helping them? Have they made a pact with a devil, who promised them extreme fortuity in exchange for their soul? Does the universe just favor them above all others, bending and twisting itself to suit their needs and desires?". Who knows? Certainly not them. A Highroller may have his or her own beliefs as to why they possess such ingrained fortitude, but they all know better than to call it into question or put it on trial, lest they jinx their luck because of it. All they truly know is that things seem to play out to their advantage very often, and that plus some rigorous training and a bit of natural talent makes them accomplished adventurers and formidable opponents.

Lucky Charm

When you choose this archetype at 3rd level, you must acquire a lucky charm. This must be worth at least 100 gp, and can be anything small enough to fit in your closed hand. This can be an item that you started out with, an item you’ve found on your adventures, or an item you’ve purchased from a merchant. You must keep this charm on your person to benefit from your Highroller abilities, and you can not use your Highroller abilities if your charm is removed from your person. If your lucky charm gets lost or destroyed, you may create another lucky charm. This must be worth at least 100 gp, must be small enough to fit in your closed hand, and you must spend at least 1 hour closely observing it to make it your lucky charm.

Heads or Tails

Starting at the 3rd level, you lose proficiency with all skills and saving throws. Whenever you make an ability check, saving throw, or attack roll, at the DM’s discretion, you may flip a coin after you see the total of your roll, but before you know the outcome. If the coin lands on heads, add a number equal to your proficiency bonus to the roll, but if the coin lands on tails, subtract a number equal to your proficiency bonus from the roll instead. You also gain proficiency with the Dice set, or any other luck based gaming set.

Lucky

Starting at 3rd level, you gain the Lucky racial trait, as described in the Halfling race description, found in Chapter 2 of the Player’s Handbook. If you are already a Halfling (or any other race that shares the feature), then your Lucky racial trait remains unchanged, but also does not count as a Highroller ability for you . You also gain the Lucky feat, as described in Chapter 6 of the Player’s Handbook. If you decide to take the Lucky feat later on, you instead gain 1 extra luck point. You may also take the Lucky feat multiple times beyond the first, but each additional selection of the Lucky feat only grants you an additional 1 luck point. These additional luck points, but not the original 3 granted to you by this ability, may still be used if you lose your lucky charm (For example, if you are a 6th level fighter and you take the Lucky feat twice, you have a total of 5 luck points, but only 2 of them may be used if you do not possess your lucky charm).

Improved Critical

Starting at 7th level, whenever you score a critical hit on an attack roll, you deal an additional amount of damage equal to your fighter level plus your proficiency bonus.

Serendipitous

Starting at 10th level, you are proficient in passive Wisdom (Perception) checks, and any that are made to find hidden objects or traps without actively searching for them are made with advantage. (To give advantage on passive checks, add 5 to the total).

Double or Nothing

Also starting at 10th level, whenever you activate your Heads or Tails ability, you may flip an additional coin after you see the result of the first coin flip, but before the DM tells you the outcome. If both coins come up heads, add a number equal to double your proficiency bonus to the check instead, but if both coins come up tails, subtract a number equal to double your proficiency bonus and deal damage to yourself, the type and amount to be decided at the DM’s discretion. If one comes up heads and the other comes up tails, nothing happens and you don’t add or subtract anything from your roll.

(Note for DMs: the type and amount of damage the player deals to themselves upon getting double tails with the Double or Nothing ability should reflect the action that the player is trying to perform. For example, if a player makes an attack roll and gets double tails, they might deal damage to themselves of the type and amount that their weapon would normally deal to an enemy)

Lucky Number

Starting at 15th level, when you activate your Heads or Tails ability, you may choose to treat a roll of 12 or lower as a 13. You must choose to activate this ability before you flip the coin. You can use this ability a number of times equal to your proficiency bonus per long rest.

Supreme Fortuity

Starting at 18th level, if an advantage and a disadvantage would cancel each other out on any type of roll, treat the roll as if you still had advantage.