Silas Blackfin - Smuggler Kingpin:

Physical Description:   Silas Blackfin is a wiry and agile human with sharp features, perpetually adorned in dark, weathered leather armor that allows for swift and silent movements. His calculating eyes, framed by a black tricorn hat, hold a constant air of suspicion. Strapped across his chest is a well-maintained pistol, which he begins fidiling with any time he becomes agitated or suspicious.   Fighting Strategy:   Silas Blackfin employs cunning hit-and-run tactics, utilizing his agility and knowledge of escape routes. He favors dirty tricks in close combat, hindering opponents while staying elusive. Silas's expertise in ranged attacks with his pistol complements his ability to keep adversaries at a distance.  
STR DEX CON INT WIS CHA
14 (+2) 18 (+4) 18 (+4) 16 (+3) 12 (+1) 18 (+4)
Statistics:
  • Armor Class: 16 (leather armor)
  • Hit Points: 168 (16d8 + 96)
  • Speed: 30 ft.
Skills:
  • Deception +8, 
  • Insight +5, 
  • Perception +5, 
  • Stealth +8
Actions:
  • Multiattack: Silas makes three attacks: two with his shortswords and one with his dagger.
  • Shortsword: Melee Weapon Attack: +8 to hit, 7 (1d6 + 4) piercing damage.
  • Dagger: Melee or Ranged Weapon Attack: +8 to hit, 6 (1d4 + 4) piercing damage.
  • Pistol Shot: Ranged Weapon Attack: +8 to hit, 9 (1d10 + 4) piercing damage.
Reactions:
  • Parry: Silas adds 3 to his AC against one melee attack that would hit him.
Traits and Features:
  • Smuggler's Network: Advantage on Charisma (Persuasion) checks related to smuggling activities.
  • Escape Routes: Advantage on Dexterity (Stealth) checks made to hide or flee.
  • Dirty Tricks: Once per turn, after hitting a creature with an attack, he can impose disadvantage on the target's next attack roll.
Weaknesses
  • Overreliance on Agility: Vulnerable to spells or abilities targeting Dexterity saves.
  • Loyalty of Associates: Associates can be exploited or turned against him.
  • Fear of Capture: Fearful of imprisonment, strategic incapacitation may yield cooperation.