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William de Wendenal, High Sheriff of Nottinghamshire

The High Sheriff of Nottinghamshire, Derbyshire and the Royal Forests is responsible for enforcing law and order and bringing criminals to justice.

The Sheriff of Nottingham is the chief official whose task it is to capture outlaws such as Robin Hood, ensure the safety of trade routes through Sherwood Forest, and to arrest outlaws for poaching the King’s deer. The Sheriff of Nottingham has a lecherous desire for Robin Hood’s lady, Maid Marian. He is widely considered to be the main villain of the Robin Hood stories, appearing in all of them, alongside such enemies of Robin Hood as Guy of Gisbourne and Prince John.

The short-staffed King of England placed the Sheriff of Nottingham in charge of law enforcement for much of northern England. The Sheriff’s influence has grown so great he attempts to take control of the throne. Although physically capable the Sheriff is more a cowardly schemer while his assistant, Guy of Gisbourne is a more competent and determined physical threat to Robin.

William de Wendenal, High Sheriff of Nottinghamshire, (Epic Toll Warden of Mammon)
Antonis Mor (1519-1575) Title Portrait of Giovanni Battista di Castaldo Date circa 1550

D&D 5E Mythological Figures: Sheriff of Nottingham

Sheriff of Nottingham DnD 5E BANNER.jpg

D&D 5E – Mythological Figures: Sheriff of Nottingham | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

In most Robin Hood tales, the villain is the Sheriff of Nottingham, a ruthless noble that overtaxes the common people and enforces the crown’s laws without mercy or any shred of kindness. Depending on the story he is sometimes a physical nemesis worthy of the highwayman, but more often than not he’s a shrewd and conniving politician with eyes on the throne. There’s some contention on who inspired the character—Sir Robert Ingram, Henry de Faucemberg, Philip Mark, Eustace of Lowdham, Ralph Murdac—but no matter the work, he is always referred to as the Sheriff of Nottingham and not by any other name because it’s about the abuse of authority more than anything else.

Sheriff of Nottingham

Medium humanoid (human), lawful evil rogue (mastermind) 6/ranger (gloom stalker) 6
Armor Class 17 (chain shirt, shield)
Hit Points 72 (6d8+6d10+12)
Speed 30 ft.

11 (+0)​14 (+2)​12 (+1)​14 (+2)​14 (+2)​17 (+3)​

Saving Throws Dex +6, Int +6
Skills Deception +11, History +10, Insight +6, Investigation +10, Persuasion +11, Stealth +10; thieves’ tools
Senses darkvision 60 ft., passive Perception 12
Languages English, Thieves’ Cant
Challenge 5 (1,800 XP)

Background: Noble. Due to his appointed position, the sheriff is treated with a measure of respect wherever he goes. He is treated as royalty (or as closely as possible) by most peasants and traders, and as an equal when meeting other authority figures (who make time in their schedule to see him if requested to do so).

Ambush Master. The sheriff gains a +2 bonus to initiative rolls. On his first turn in combat, the sheriff’s speed increases by 10 feet until the end of his turn and if he takes the Attack action, he can make an additional weapon attack. On a hit, the additional attack deals 1d8 extra damage.

Cunning Action (1/Turn). The sheriff can use a bonus action to take the Dash, Disengage, Help, or Hide action.

Darkstalker. The sheriff is invisible to creatures that rely on darkvision to see in darkness while he is in darkness.

Fast Learner. After the sheriff has heard a creature speak for 1 minute or longer, he can mimic its manner of speaking as long as he knows the same language as the creature (allowing him to seem like he is local to a given region).

Favored Enemy. The sheriff has advantage on Wisdom (Survival) checks to track humans and beasts, as well as on Intelligence checks to recall information about them.

Feat: Diplomatic. The sheriff can make a Charisma (Persuasion) check contested by the Wisdom (Insight) check of a creature that can understand what he says during 1 minute of talking. On a success, as long as the sheriff remains within 60 feet of it (and for 1 minute afterward) the target is charmed by him. The sheriff automatically fails on the check if he or his companions are fighting the target.

Feat: Master of Intrigue. When the sheriff takes the Attack action, instead of making one of his attacks he can try to fool one humanoid he can see within 30 feet of him. The target must be able to hear him make a Charisma (Deception) check contested by its Wisdom (Insight) check. On a success, the target is fooled until the end of the sheriff’s next turn or until he attempts to fool a different target. The sheriff doesn’t provoke opportunity attacks from movement around a fooled target and he has advantage when attacking a fooled target. On a failure, the sheriff can’t fool the target for 1 hour.

Natural Explorer. When the sheriff makes an Intelligence or Wisdom check related to forests or grasslands, 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, the sheriff gains the following benefits:

  • Difficult terrain doesn’t slow his group’s travel.
  • The sheriff’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), the sheriff remains alert to danger.
  • If he is traveling alone, the sheriff can move stealthily at a normal pace.
  • When he forages, the sheriff finds twice as much food as he normally would.
  • While tracking other creatures, the sheriff also learns their exact number, their sizes, and how long ago they passed through the area.

Poisoned Bolts. The sheriff carries 12 poisoned hand crossbow bolts.

Sneak Attack (3d6, 1/Turn). The sheriff deals an extra 10 (3d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the sheriff that isn’t incapacitated and the sheriff doesn’t have disadvantage on the attack roll.

Spellcasting. The sheriff is a 6th level spellcaster that uses Wisdom as his spellcasting ability (spell save DC 14; +6 to hit with spell attacks). He has the following spells prepared from the ranger’s spell list:

1st-level (4 slots): disguise self, hunter’s mark, longstrider

2nd-level (2 slots): find traps, pass without trace, rope trick

Tactician. The sheriff is able to use the Help action to aid an ally attacking a creature as long as the target of the attack is able to see and hear the sheriff and is within 30 feet of him.

Extra Attack. The sheriff attacks twice.

Dagger. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 6 (1d4+4) piercing damage.

Shortsword. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 7 (1d6+4) slashing damage.

Dagger. Ranged Weapon Attack: +6 to hit, range 20/60 ft., one target. Hit: 4 (1d4+2) piercing damage.

Hand Crossbow. Ranged Weapon Attack: +6 to hit, range 30/120 ft., one target. Hit: 5 (1d6+2) piercing damage. A creature must make a DC 14 Constitution saving throw or take 10 (3d6) poison damage.

Primeval Awareness. The sheriff expends one ranger spell slot to focus his awareness on the region around him. For 1 minute per level of the spell slot he expends, the sheriff 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 or grassland): aberrations, celestials, dragons, elementals, fey, fiends, and undead. This feature doesn’t reveal the creatures’ location or number.

Uncanny Dodge. When an attacker the sheriff can see hits him with an attack, the sheriff can use his reaction to halve the attack’s damage against him.

William de Wendenal, High Sheriff of Nottinghamshire, Epic Toll Warden of Mammon

William de Wendenal, High Sheriff of Nottinghamshire, Epic Toll Warden of Mammon
Rogue 10, Toll Warden of Mammon 13
Medium humanoid (Kin)
Hit Dice23d6+23 (106 hp)
Initiative+15 (+11 Dexterity, +4 Improved Initiative)
Speed40 ft. (8 squares) with boots of swiftness; base speed 20 ft. (4 squares)
Armor Class34 (+11 Dexterity, +1 size, +7 armor, +5 deflection), touch 27, flat-footed 23
Base Attack/Grapple+16/+12
Attack+5 wounding dagger +33 melee or +33 ranged (1d4+5 plus 1 Constitution/19-20); or +2 frost light
(with +1 keen bolts) +16 ranged (1d8+2 plus 1d6/17-20)
Full Attack+5 wounding dagger +33/+28/+23/+18 melee or +33 ranged (1d4+5 plus 1 Constitution/19-20); or +2 frost light crossbow (with +1 keen bolts) +16 ranged (1d8+2 plus 1d6/17-20)
Space/Reach5 ft./5 ft.
Special AttacksDemand toll 4/day, master of misappropriation, sneak attack +8d6
Special Qualities20% concealment, greater collect, improved evasion, improved uncanny dodge, nondetection, trapfinding, trap sense +3, uncanny dodge, vanishing vault, weigh the wealth
SavesFort +9, Ref +27, Will +8
AbilitiesStrength 10, Dexterity 32, Constitution 12, Intelligence 14, Wisdom 10, Charisma 16
SkillsAppraise +31, Balance +40, Bluff +10, Climb +27 (+29 to a rope), Diplomacy +7, Disable Device +26, Disguise +10 (+12 when acting in character), Escape Artist +40 (+42 when escaping rope bonds), Hide +54, Intimidate +13, Jump +29, Listen +11, Move Silently +47, Open Lock +29, Sleight of Hand +59, Sense Motive +10, Tumble +45, Rope Use+17 (+19 to bind someone)
FeatsCheat, Deft Hands, Devotee of Darkness (Mammon), Improved Initiative, Skill Focus (Appraise), Skill Focus (Sleight of Hand), Weapon Finesse
Epic FeatsEpic Skill Focus (Sleight of Hand), Lord of Legerdemain
EnvironmentAny land or underground
OrganizationSolitary (unique)
Challenge Rating23
Treasure58,726 gp, +2 frost light crossbow, +5 wounding dagger, +5 greater slick leather armor, Backpack, belt pouch (with 100 sp), boots of swiftness, crowbar, Nobles outfit, mantle of great stealth, masterwork thieves’ tools, ring of invisibility, ring of protection +5, silk rope (50 ft.), trail rations (x2), quiver (with 50 +1 keen bolts), waterskin
AlignmentLawful evil

William has received a +4 inherent bonus to his Dexterity score.

Sheriff of Nottingham

The Sheriff of Nottingham Rhead, Louis. “Bold Robin Hood and His Outlaw Band: Their Famous Exploits in Sherwood Forest”. New York: Blue Ribbon Books, 1912, page 129

Demand Toll (Sp): 1/day, William can command that an item or sum of money be surrendered to him. This affects one target within range of his voice, who is entitled to a Will save (DC 26). Success means that the target is dazed for 1d3 rounds, whilst failure means acceding to the demand as well as being dazed for 1d3 rounds. Should the target not have the specified item or sum of money, or should the toll warden not specify which item is to be paid, the target automatically succeeds (and is dazed for 1d3 rounds). The most valuable item possessed by the target grants the target a +4 bonus on his saving throw; the second most valuable item grants a +2 bonus; and lesser items grant no bonus. This is a mind-influencing, language dependent ability.

Devotee of Darkness: Once per day, William can call upon the aid of Mammon, granting him a +3 profane bonus to any one roll. Against chaotic or good foes, William gains a +1 profane bonus to Armor Class, and once per day can gain a +2 profane bonus on saving throws against a spell with the chaotic or good descriptor. He also gains Spell Resistance 23 against chaotic and good spells and spell-like abilities.

Whenever dealing with a higher-ranking servant of Mammon (or the Lord of the Avarice himself), William takes a –2 penalty on attacks, checks, and other rolls, a – 3 penalty to Armor Class, and a -6 penalty to saving throws. In addition, no Spell Resistance William obtains is ever effective against such creatures.

Greater Collect (Ex): William is exceptionally skilled at “collecting taxes”, gaining a +11 profane bonus on Sleight of Hand checks. He may always take 10 on Sleight of Hand checks. Furthermore, he can take items one size category larger than normal, and hide them on his person as a supernatural ability. The base Sleight of Hand DC to lift a larger object from an individual is 30, and the opponent gains a +5 circumstance bonus on the opposed Spot check to notice the ‘collection’.

Master of Misappropriation (Su): William has become an accumulator of others’ wealth par excellence. Any creature targeted by his demand toll ability that fails its saving throw must continue to make a saving throw round by round; William continues to make demands until a successful save is made, although the save DC decreases by -1 each round. This still counts as only one use of demand toll. Additionally,
he can discern location 1/ week to find any object he has touched.

Tincture of Treasure (Su): William hates the thought of wealth in the hands of others, and constantly detects nearby objects worth at least 333 gp (as though by a detect spell with a 10 foot radius, centered on himself). By concentrating on the effect (a move action that does not provoke attacks of opportunity), William can discover more information. The first round (always active) allows him to ascertain whether there are objects at least 333 gp in the vicinity (items or coins kept in the same container count as one object). The second round shows him the approximate location and number of places where such wealth is kept. The third round gives an approximation of the value of the item(s), as long as William succeeds on an Appraise check (increase the DC by 10 if the items cannot be seen) as a free action. A separate check is required for each aura. William can only use the Appraise skill to determine the mundane (non-magical) value of an item.

Vanishing Vault (Su): William stores his wealth in an extraplanar vault, akin to a bag of holding, which only he can access. There is no weight limit, but there is a space limit (William’s vault is a 130 foot cube). The vault cannot be entered; its only purpose is to store items until they are needed. William can access his vault as standard action, using the opening to any container or bag, so long as said container or bag is either his own or is unattended.

Weigh the Wealth (Su): William hates the thought of wealth in the hands of others, and constantly detects nearby coins or items (as though by a detect spell with a 30 foot radius, centered on himself). William can instinctively assess the approximate value of the nearby treasure (as per Table above). He may make on Appraise check on each aura as a free action to gain a more accurate indication of the treasure’s worth. If the item is magical, he can assess the value of the item but does not gain any insight as to what enchantments are in effect. Assume that magical items have a base Appraise DC of 20 +1 per 2,000 gp of value.

William has become so attached to his ill-gotten gains that the loss of even a copper penny will not go unnoticed. Should William lose or surrender any item he has had on his person for more than 3 hours, he is able to use locate object at will to find said item.

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