Caballero

To a Caballero, war is the highest form of strategic contest, and how you win is just as important as winning itself. All due courtesy and respect are given to worthy opponents, and needless cruelty or cheap shots are beneath them. Once the engagement begins, however, sentiment has no place on the battlefield. A Caballero studies every movement, exploits every weakness, and presses every advantage until the contest is decided. By weaving together precise marksmanship with their studious understanding of warfare, Caballeros control the tempo of a fight with remarkable efficiency. For the Caballero, each contest is a chance to demonstrate that preparation, discipline, and flawless execution are the deadliest weapons of all.

Level 3: Gentlemanly Warfare

You fight like a gentleman, and a gentleman never strikes without warning.

Whenever you roll Initiative, you may address one creature you can see and announce your violent intent to them.

Until the end of that creature’s first turn in combat:

The creature has disadvantage on all attack rolls.

Your allies have advantage on attack rolls made against that creature.

You have disadvantage on attack rolls made against that creature.

Level 3: On the Back Foot

You know how to capitalize on your enemy’s hesitation and missteps.

Whenever you make an attack roll against a creature that is suffering from disadvantage, you gain the following benefits:

• You gain a bonus to the attack roll against that creature equal to your Proficiency Bonus.
• On a hit against that creature, you deal additional damage equal to your Proficiency Bonus.

Level 6: Master of Your Craft

Your training extends beyond the battlefield into every application of your weapon.

You may add your Proficiency Bonus to any non-combat ability check you make that involves a weapon with which you are proficient. This is in addition to any bonuses normally added due to proficiency or expertise in the chosen skill.

This may include, but is not limited to:

• Identifying weapon use or residue (Investigation, Nature)
• Demonstrating precision or control with your weapon (Performance)
• Applying pressure or threat (Intimidation)

Level 6: Battle Plans [Maneuver]

Whenever you miss an attack against a creature that is suffering from disadvantage, you may expend a risk die to treat the roll as a 10. 

Level 10: Composed Execution

You do not lose composure when the battle turns grim...your enemies are not afforded the same luxury.

Whenever you reduce a creature that is suffering from disadvantage to 0 Hit Points, you may immediately give another creature that you can see within 60 feet of you disadvantage on all ability checks and saving throws until the end of their next turn.

You can use this feature a number of times equal to half your Proficiency Bonus (rounded down), and you regain all expended uses when you finish a long rest.

Level 14: Inevitable Conclusion [Maneuver]

Whenever you deal a critical hit against a creature that is suffering from disadvantage, you may expend two Risk Die to have the attack deal maximum damage.