The Way of the Streetwise Brawler is a monk subclass deeply rooted in the unforgiving streets of Toraveno, where cunning, resilience, and raw power are essential for survival. Monks who follow this path master the art of using their bodies as weapons and embrace the unorthodox techniques of street fighting. This specialization hones their abilities to navigate the complex underbelly of Toraveno, blending skillful martial arts with a street-savvy approach to combat.

At 3rd level, these monks gain proficiency in the Intimidation skill, reflecting their capacity to instill fear in adversaries. They can wield all improvised weapons as monk weapons, adapting their fighting style to the tools at hand. Their Dirty Tactics feature allows them to deploy various effects in battle, such as disorienting enemies or grappling them with ease, highlighting their resourcefulness in high-pressure situations.

By 6th level, Streetwise Brawlers become proficient in Constitution saving throws and can gain temporary hit points using their Flurry of Blows feature. This resilience and durability serve them well in street fights and intense skirmishes. Their resourcefulness is further enhanced at 11th level when they gain the ability to narrowly escape death by dropping to 1 hit point when reduced to 0.

Finally, at 17th level, these monks can unleash their Gang Leader's Presence, an aura of authority and danger that commands respect and fear. By intimidating foes and stunning them with their strikes, Streetwise Brawlers can take control of the chaotic streets of Toraveno and become feared figures in the city's underworld.

Character Aspects and Inspirations:
Players who choose the Way of the Streetwise Brawler subclass should consider the following aspects when creating their character:

• Street Smarts: Develop a backstory that involves growing up in Toraveno's rough neighborhoods, learning to survive through tough and cunning means.
• Resourcefulness: Embrace a pragmatic approach to combat and problem-solving, making the most of available resources, including improvised weapons and dirty tactics.
• Authority and Intimidation: Your character may have a reputation for being intimidating or commanding respect among other denizens of Toraveno.
• Loyalty and Rivalry: Consider your character's relationship with the different factions and gangs in the city. Are they loyal to one group, or do they operate independently?
• Urban Survivalist: Draw inspiration from characters who thrive in urban environments, such as streetwise heroes or antiheroes in noir fiction.

With these aspects in mind, your Streetwise Brawler monk can navigate Toraveno with confidence, exploiting its dangers and opportunities while making a name for themselves in the shadows of the city.

Bonus Proficiencies

Your experience in the urban underworld grants you proficiency in theIntimidation skill.

Additionally, improvised weapons count as monk weapons for you. When you hit a creature with an improvised weapon, you can choose to either deal an additional 1d4 damage or impose one of the following effects:

• Knock the target prone
• Disarm the target (make a Strength saving throw against your Monk save DC to avoid losing hold of one object the creature is holding).

This bonus damage increases to 1d6 at 11th level.

Dirty Tactics

You gain the ability to fight dirty when necessary. When you use the [action]Attack[action/] action and hit a creature with an unarmed strike or monk weapon attack, you can choose to apply one of the following Dirty Tactics by spending 1 Ki point:

Distracting Strike: The target must make a Wisdom saving throw (Your Monk save DC) or have disadvantage on its next attack roll against a creature other than you.

Disorienting Strike: The target's movement speed is reduced to 0 until the start of your next turn.

Grip Strike: When you make an unarmed strike against a creature, you can use a bonus action to attempt to grapple or shove the target as part of the same attack. You gain advantage on any Strength (Athletics) check you make to initiate or resist a grapple or shove.

 

Ruthless Resilience

Starting at 6th level, you've learned to shrug off pain and discomfort with the hardened resolve of a streetwise brawler.

When you use your Flurry of Blows or Dirty Tactics feature, you can pay 1 additional Ki point to gain temporary hit points equal to your Wisdom modifier + twice your proficiency bonus.

Bloody Knuckle Defiance

Your experience in the rough world of back-alley brawling has toughened your body and spirit.

• When you are reduced to 0 hit points but not killed outright, you can use your reaction and expend 3 Ki points to drop to 1 hit point instead. Once you use this feature, you can't use it again until you finish a long rest.

• When you are dealt critical damage, you can regain 2 Ki points. This feature can be used 3 times before you must complete a long rest.

Gang Leader's Presence

Upon reaching 17th level, You exude an aura of authority and danger that commands respect even in the chaotic streets of Toraveno.

As an action, you can spend 5 Ki points to activate your Gang Leader's Presence. For the next minute:

• You have advantage on all Charisma-based ability checks and Charisma saving throws.
• When you hit a creature with an unarmed strike or monk weapon attack, you can choose to expend 2 Ki points to make the target frightened of you until the end of your next turn. A creature frightened by this ability must also make a Wisdom saving throw against your Monk save DC or be stunned until the end of their next turn.

Once you use this feature, you can't use it again until you finish a short or long rest.