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Sir Guy of Gisbourne

Cesare Dandini (1596-1657) Title: Portrait of a Young Soldier with a Lance Date first half of 17th century, Guy of Gisbourne
Cesare Dandini (1596-1657) Title: Portrait of a Young Soldier with a Lance Date first half of 17th century

Sir Guy of Gisborne hunts Robin Hood for the Sheriff of Nottingham.

Known for his cruelty and murders, he is a suave nobleman and the Sheriff of Nottingham’s second-in-command.

While Robin was away fighting in the crusades, Guy managed his estate, and takes it when Robin is outlawed. A dark character with skewed morals, he is an active enforcer of the Sheriff’s cruelty, but at the same time, he is in love with Marian, showing conflicted attempts to redeem himself in her eyes. He pursues her, eventually proposing to her.

He is cruel, ruthless, and diabolically clever. Although he serves the Sheriff of Nottingham, he’s in contact with the French minister Richelieu and intendes to seize power for himself, after the Sheriff topples the king. Assassinating the Sherriff to become the English King.

D&D 5E Mythological Figures: Sir Guy of Gisborne

D&D 5E – Mythological Figures: Sir Guy of Gisborne | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

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Little John and Robin Hood are strolling through the woods (sometime in 1650, or maybe even as early as 1475) as the legendary highwayman recounts a recent dream of being attacked by a pair of warriors. Suddenly they see a fellow unknown to them leaning on a tree up ahead—being the big burly guy he is, Little John offers to check this stranger out but Robin Hood gets angry at the suggestion, threatening injury for the perceived insult of cowardice. Little John takes offense and leaves, soon after captured by the Sheriff of Nottingham and soon to be hanged. This newcomer is clad in horse-hide from his head on down: Guy of Gisborne, a killer hired by the sheriff to hunt down and slay Robin Hood.

The two have it out with an archery contest (which of course the heroic highwayman easily wins) and then after identifying who he is a fight ensues. Robin Hood is stabbed by the assassin but takes the killing blow, slaying and then decapitating Guy, blowing his horn to tell the sheriff of victory, defacing his head, and donning his garb. Robin Hood wears his would-be killer’s unique accoutrements and carries what is supposedly his own head (now unrecognizable) to the sheriff and the guise works—after persuading the sheriff to let him execute Little John, instead he frees his friend who then fires an arrow through the villainous noble’s heart.

Design Notes: A killer hired by the Sheriff of Nottingham is probably a soldier so Guy here’s got a little bit of ranger (he is a hunter right?) and then a lot of fighter, going with brute because let’s be honest—people that wear horses are not exactly subtle. Let’s do the numbers! The DMG comes in at 6.5, the Blog of Holding 7.6, so everything averages out a wee bit past CR 7.

Sir Guy of Gisborne​

Medium humanoid (human), neutral evil ranger (hunter) 3/ fighter (brute) 8
Armor Class 17 (hide, shield, defensive fighting style)
Hit Points 93 (11d10+33)
Speed 30 ft.

16 (+3)​14 (+2)​16 (+3)​10 (+0)​11 (+0)​10 (+0)​

Saving Throws Str +7, Dex +6
Skills Athletics +7, Insight +4, Intimidation +4, Stealth +6, Survival +4; gaming set, vehicles (land)
Senses passive Perception 10
Languages Common
Challenge 7 (2,900 XP)

Background: Soldier. Guy commands respect in the army. Soldiers loyal to the crown know he is their superior, and he can use his influence to temporarily requisition simple equipment or horses, or gain entrance to military fortresses and outposts.

Action Surge (1/Short rest). Once on his turn, Guy can take an additional action on top of his regular action and a possible bonus action.

Brutal Toughness. Guy gains a +1d6 bonus to saving throws and death saves (treating final results of 20 or higher on a death saving throw as a natural 20).

Colossus Slayer (1/Turn). When Guy hits a creature with a weapon attack, the creature takes an extra 4 (1d8) damage if it’s below its hit point maximum.

Favored Enemy. Guy has advantage on Wisdom (Survival) checks to track humans, half-elves, and half-orcs, as well as on Intelligence checks to recall information about them.

Natural Explorer (Forests). When Guy makes an Intelligence or Wisdom check related to forests, his proficiency bonus (+4) is doubled if he is using a skill that he’s proficient in. While traveling for an hour or more in his favored terrain, Guy gains the following benefits:

  • Difficult terrain doesn’t slow his group’s travel.
  • Guy’s group can’t become lost except by magical means.
  • Even when he is engaged in another activity while traveling (such as foraging, navigating, or tracking), Guy remains alert to danger.
  • If he is traveling alone, Guy can move stealthily at a normal pace.
  • When he forages, Guy finds twice as much food as he normally would.
  • While tracking other creatures, Guy also learns their exact number, their sizes, and how long ago they passed through the area.

Second Wind (1/Short Rest). On his turn, Guy can use a bonus action to regain 1d10+8 hit points.

Spellcasting. Guy is a 3rd level spellcaster that uses Wisdom as his spellcasting ability. He knows the following ranger spells:

1st-level (3 slots): hunter’s mark, jump, longstrider​

Extra Attack. Guy attacks twice when he takes the Attack action.

Shortsword. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 11 (1d6+1d4+5) piercing damage.

Longbow. Ranged Weapon Attack: +6 to hit, range 150/600 ft., one target. Hit: 9 (1d8+1d4+2) piercing damage.

Primeval Awareness. Guy can expend one ranger spell slot to focus his awareness on the region around him. For 1 minute per level of the spell slot he expends, Guy can sense whether the following types of creatures are present within 1 mile of him (or within up to 6 miles if he is in a forest): aberrations, celestials, dragons, elementals, fey, fiends, and undead. This feature doesn’t reveal the creatures’ location or number.

Name Sir Guy of Gisbourne
Human CR 12
XP 19200
Any Medium Humanoid
Fighter level 6 (skill points 30) Knight
(Cad )
Antipaladin level 6 (skill points 30) Antipaladin
Assasin level 4 (skill points 28) Assasin
Init +1; Senses ; Perception +11


AC 15, touch 11, flat-footed 14 (+1 Dex, +3 armour, +1 shield)
hp 110 (0d8+6d10+6d10+4d8+16+6);
Fort +13, Ref +10, Will +6


Speed 30ft.
Melee +2 Bane Sword bastard +19/+14/+9 (1d10+3/19-20), MWK Dagger +11 (1d4+1/19-20)
Ranged MWK Crossbow, light +17 (1d8 /19-20 X2) range 80
Space 5 ft.; Reach 5 ft.


Special Attacks
Channel negative energy (Su) Consumes two uses of his touch of corruption ability. As a cleric of antipaladin level
Death Attack If an assassin studies his victim for 3 rounds and then makes a sneak attack with a melee weapon that successfully deals damage, the sneak attack has the additional effect of possibly either paralyzing or killing the target (assassins choice). Studying the victim is a standard action. The death attack fails if the target detects the assassin or recognizes the assassin as an enemy (although the attack might still be a sneak attack if the target is denied his Dexterity bonus to his Armor Class or is flanked). If the victim of such a death attack fails a Fortitude save (DC 10 + the assassins class level + the assassins Int modifier) against the kill effect, she dies. If the saving throw fails against the paralysis effect, the victim is rendered helpless and unable to act for 1d6 rounds plus 1 round per level of the assassin. If the victims saving throw succeeds, the attack is just a normal sneak attack. Once the assassin has completed the 3 rounds of study, he must make the death attack within the next 3 rounds.

If a death attack is attempted and fails (the victim makes her save) or if the assassin does not launch the attack within 3 rounds of completing the study, 3 new rounds of study are required before he can attempt another death attack.

DC 10 + assassin level + INT mod
Dirty Maneuvers (Ex) Skilled at deceiving and discomfiting his opponents. The cad gains a bonus on disarm, dirty trick, and steal combat maneuver checks. The cad also gains a bonus to CMD when attacked with the disarm, dirty trick, and steal combat maneuvers. Bonus = 2
Fiendish Boon (Sp) SA increase weapon enchantment for 1 minute by 1
Payback (Ex) Gains a bonus on attack and damage rolls against any creature that has attacked the cad since the beginning of his last turn. Bonus = 1
Smite Good Add CHA bonus to hit , +1/level to damage. Per day = 2
Sneak Attack Sneak attack at an extra (D6) 2
Touch of Corruption (Su) 1/2 his antipaladin level + his Charisma modifier /day. 1d6 dam /2 levels
True Death (Su) DC 15 + level to bring back alive
Spells Known:
Antipaladin Spells: CL 6 Concentration 7Level 1 (2) DC 12: Command, Detect Poison, ;STATISTICSStr 13, Dex 13, Con 13, Int 15, Wis 11, Cha 13
Base Atk +15; CMB +16; CMD 28
Feats Blind-fight, Combat Expertise, Spirited Charge, Weapon Focus, Cruelty (Su) – Dazed, Cruelty (Su) – Shaken, Animal Affinity, Armour Prof Light, Catch off Guard, Cleave, Exotic Weapon Prof, Martial Weap Prof, Mounted Archery, Mounted Combat, Power Attack, Ride-by Attack, Selective Channeling, Shield Proficiency, Simple Weapon Proficiency, Trample;
Skills Acrobatics +12, Appraise +3, Bluff +12, Climb +5, Diplomacy +8, Disable Device +1, Disguise +7, Escape Artist +0, Handle Animal +10, Intimidate +12, Know Arch & Eng +2, Know Dungeon +2, Know Geography +3, Know Local +4, Know Religion +7, Linguistics +7, Perception +11, Perform Dance +1, Ride +20, Sense Motive +10, Sleight of Hand +5, Spellcraft +7, Stealth +10, Survival +5, Swim +3, Use Magic Device +5
Languages Common


Environment Any
Organization Company 10-20, Band 30-100, Squad 4-8
Treasure Standard

ITEMS: Masterwork Studded Leather, +2 Sword, bastard, Bane : Against a designated foe, enhancement bonus is +2 better and +2d6 points of damage., Masterwork Dagger, Masterwork Crossbow, light,

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