The Winchester Family are Men of Letters and hunters. The Winchester bloodline goes back to their ancestors Cain and Abel. Mary Winchester comes from a family of hunters, while the Winchester line was traditionally Men of Letters. Sam and Dean Winchester were destined to be the vessels of Archangel Michael and Lucifer.
Dean Winchester (b. January 24, 1979) is a human and hunter as well as a member of the Men of Letters with his younger brother Sam. He and his brother are members of the Winchester and Campbell families. Through his father, Dean is the older half-brother of Adam Milligan.
Samuel “Sam” William Winchester (b. May 2, 1983) is a hunter as well as a Man of Letters, along with his older brother Dean. He is one of the main protagonists of Supernatural. Both Sam and Dean are related to the Winchester and Campbell families – a Letters family and a Hunting family respectively. The pair also shares a bloodline with Cain and Abel. Because of this, Sam was predestined to be the true vessel of the fallen archangel Lucifer (whilst Dean was Michael’s).
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Dean Winchester
Medium humanoid (human), neutral good
Armor Class 13
Hit Points 130 (20d8 + 40)
Speed 30 ft.
Abilities Str 14 (+2), Dex 13 (+1), Con 14 (+2), Int 11 (+0), Wis 15 (+2), Cha 14 (+2)
Saving Throws Str +5, Dex +4, Wis +5, Cha +5
Skills Athletics +5, Arcana +3, Insight +5, Intimidation +5, Medicine +5, Perception +5, Religion +5, Stealth +4
Senses passive Perception 15
Languages English
Challenge 6 (2,300 XP)
Blessing of the Winchesters. Dean’s AC includes his Charisma bonus.
Enochian Branding. Dean can’t be targeted by any divination magic cast by fiends or perceived through magical scrying sensors used by fiends.
Innate Spellcasting. Dean’s spellcasting ability is Intelligence (spell save DC 11). He can innately cast the following spells:
- 1/day each: banishment, dispel evil and good, protection from evil and good
Legendary Resistance (1/Day). If Dean fails a saving throw, he can choose to succeed instead.
Winchester Tenacity. When Dean dies, he must make a DC 10 Charisma saving throw. On a success, Dean returns to life in 1d12 months. He returns to his original body, a new body or through some other appropriate vessel (GM’s discretion).
Actions
Multiattack. Dean makes two attacks with his pistol or two attacks with his knife.
Demon-Killing Knife of the Kurds. Melee or Ranged Weapon Attack: +6 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 5 (1d4 + 3) radiant damage, and if the target is a fiend, it must make a DC 13 Charisma saving throw. On a failed saving throw, the target takes 17 (5d6) radiant damage.
Automatic Pistol. Ranged Weapon Attack: +4 to hit, range 50/150, one target. Hit: 8 (2d6 + 1) piercing damage.
Sawed-Off Shotgun. Dean fires his sawed-off shotgun, sending shot in a 15-cone. Each creature in the area must make a DC 13 Dexterity saving throw, taking 9 (2d8) piercing damage on a failed saving throw or half as much damage on a success. To use this action again, Dean must use his bonus action to reload the shotgun.
Legendary Actions
Dean can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Dean regains spent legendary actions at the start of his turn.
Attack. Dean makes an attack with his pistol.
Detect. Dean makes a Wisdom (Perception) check.
Intimidate (Costs 3 Actions). Dean intimidates a target within 30 feet of him that is aware of him, making a Charisma (Intimidation) check contested by the target’s Wisdom (Insight). If the contest is successful, the target is frightened until the end of its next turn.
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Sam Winchester
Medium humanoid (human), neutral good
Armor Class 13
Hit Points 130 (20d8 + 40)
Speed 30 ft.
Abilities Str 14 (+2), Dex 13 (+1), Con 14 (+2), Int 13 (+1), Wis 15 (+2), Cha 15 (+2)
Saving Throws Dex +4, Int +4, Wis +5, Cha +5
Skills Athletics +5, Arcana +3, History +5, Insight +5, Perception +5, Persuasion +5, Religion +5, Stealth +4
Senses passive Perception 15
Languages English, Latin
Challenge 6 (2,300 XP)
Blessing of the Winchesters. Sam’s AC includes his Charisma bonus.
Enochian Branding. Sam can’t be targeted by any divination magic cast by fiends or perceived through magical scrying sensors used by fiends.
Innate Spellcasting. Sam’s spellcasting ability is Intelligence (spell save DC 12). He can innately cast the following spells:
- 3/day each: dispel evil and good, protection from evil and good
- 1/day each: banishment
Legendary Resistance (1/Day). If Sam fails a saving throw, he can choose to succeed instead.
Winchester Tenacity. When Sam dies, he must make a DC 10 Charisma saving throw. On a success, Sam returns to life in 1d12 months. He returns to his original body, a new body or through some other appropriate vessel (GM’s discretion).
Actions
Multiattack. Sam makes two attacks with his pistol or two attacks with his angel blade.
Angel Blade. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 7 (1d6 + 4) piercing damage, and if the target is a celestial or a fiend, it must make a DC 13 Charisma saving throw. On a failed saving throw, the target takes 27 (5d10) force damage.
Automatic Pistol. Ranged Weapon Attack: +4 to hit, range 50/150, one target. Hit: 8 (2d6 + 1) piercing damage.
Sawed-Off Shotgun. Sam fires his sawed-off shotgun, sending shot in a 15-cone. Each creature in the area must make a DC 13 Dexterity saving throw, taking 9 (2d8) piercing damage on a failed saving throw or half as much damage on a success. To use this action again, Sam must use his bonus action to reload the shotgun.
Legendary Actions
Sam can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Sam regains spent legendary actions at the start of his turn.
Attack. Sam makes an attack with his pistol.
Detect. Sam makes a Wisdom (Perception) check.
Exorcism (Costs 3 Actions). Sam casts dispel evil and good.
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I would bump Dean’s Con score up, because if you remember he was tortured in hell, and has gone through some pretty rough encounters and can manage pretty well. I’d move it up to a 16. Sam is the one who is usually found researching in the libraries, online (can also hack), and is the most familiar with the men of letters files. I would bump his Intelligence score up closer to a 15 or 16 because of these traits.