In Mythological Figures today we’re headed after a person that is more popular in terms of ancient Western mythologies than probably anyone else: Odysseus/Ulysses!
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Odysseus is known for two principal things: his role in the Trojan War (recounted in The Illiad) and his long, perilous journey back home collectively known as The Odyssey. If you find yourself saying, “that word looks familiar…” that’s what I’m talking about with Odysseus’ lasting popularity--the whole reason we have a word for “a long series of wanderings or adventures, especially when filled with notable experiences, hardships, etc.” is this guy right here. I’ve no intention to repeat the entirety of that trip here and instead refer folks to better resources for that (Wikipedia, Video SparkNotes, full text at The Internet Classics Archive). Suffice to say that of the many greek heroes, Odysseus is Captain Greece.

Design Notes: Odysseus needs to be a few things--he’s got to be clever and wise, have some agility, he’s not weak, and he’s good with a bow. With that in mind we’ve got our first ranged battlemaster build with a healthy dose of mastermind rogue to reflect his legendary cunning. The archery fighting style and a smattering of feats fill out the rest of his iconic profile, with Expertise ramping up the essential skills for his many successes to whopping +15s. For the CR equation this time around the DMG said 10.6, the Blog of Holding rubric claimed 11, and I’m inclined to agree with the latter--Odysseus here is definitely a considerably dangerous foe and as long as he’s not wasted in a suicidal charge will be an NPC that adventurers will quickly decide to focus their ire upon.


Odysseus
Medium humanoid (human), rogue (genius) 9/fighter (master of battle) 11

Armor Class 17 (breastplate or 19 with shield)
Hit Points 101 (9d8+11d10)
Speed 30 ft.

STR
DEX
CON
INT
WIS
CHA
12 (+1)
16 (+3)
10 (+0)
16 (+3)
16 (+3)
14 (+2)

Saving Throws Dex +9, Int +9
Skills Deception +14, History +9, Insight +15, Investigation +15, Perception +9, Persuasion +14
Tools gaming set +6, thieves’ tools +6
Senses passive Perception 19
Languages Common, two other languages
Challenge 11 (7,200 XP)

Background: Noble - Prince. Due to his position as a noble, Odysseus 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 (at least until it is clear he is quite mad), and as an equal when meeting other authority figures (who make time in their schedule to see him if requested to do so).

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

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

Evasion. When Odysseus is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.

Fast Learner. After Odysseus 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).

Feat: Brilliant. Odysseus always knows how long it will be before the next sunset or sunrise, the northerly direction, and can perfectly remember anything he’s experienced within the last 31 days.

Feat: Diplomatic. Odysseus 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 Odysseus remains within 60 feet of it (and for 1 minute afterward) the target is charmed by him. Odysseus automatically fails on the check if he or his companions are fighting the target.

Feat: Moderate Protection Master. Odysseus adds +3 from Dexterity instead of +2 when he is wearing medium armor.

Feat: Superb Aim. Odysseus ignores half cover and three-quarters cover when making a ranged weapon attack, and he doesn’t have disadvantage when attacking at long range. When Odysseus makes his first ranged weapon attack in a turn, he can choose to take a -5 penalty to his ranged weapon attack rolls in exchange for a +10 bonus to ranged weapon damage.

Indomitable (1/Long Rest). Odysseus can reroll a saving throw that he fails but must use the new roll.

Maneuver Master (5d10/Short Rest). Odysseus can expend a maneuver dice to perform a single maneuver with an attack.

  • Command. Odysseus uses his bonus action to forgo one of his attacks and direct a friendly creature who can see or hear him. The creature uses its reaction and makes a weapon attack, dealing 1d10 extra weapon damage on a successful hit.
  • Disarm. A creature Odysseus has hit with an attack takes 1d10 additional damage and makes a DC 17 Strength saving throw or drops one held item of his choice.
  • Inspire. Odysseus uses a bonus action and chooses an ally able to see and hear him. That ally gains 1d10+2 temporary hit points.
  • Maneuver. On a successful hit with a weapon attack, Odysseus deals 1d10 extra damage and chooses a friendly creature that can see and hear him. That creature can move half its speed by using its reaction. This movement does not provoke opportunity attacks from the target of Odysseus’ attack.
  • Trip. Odysseus deals 1d10 additional damage and if the target is a creature of Large size or smaller, it makes a DC 17 Strength saving throw or is knocked prone.


Second Wind (1/Short Rest). On his turn, Odysseus can use a bonus action to regain 1d10+11 hit points.

Sneak Attack (1/Turn). Odysseus deals an extra 17 (5d6) 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 Odysseus that isn’t incapacitated and Odysseus doesn’t have disadvantage on the attack roll.

Tactician. Odysseus 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 Odysseus and is within 30 feet of him.

Tactician’s Insight. After Odysseus has observed or interacted with a creature for 1 minute, he learns whether or not it has higher or lower Intelligence, Wisdom, or Charisma scores than him. In addition, he learns if the target has more or fewer class levels than him. Odysseus also knows when he and the target have equal scores in one of these categories.


ACTIONS
Extra Attack. Odysseus attacks three times.
Shortsword. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 6 (1d6+3) piercing damage.
Longbow. Ranged Weapon Attack: +11 to hit, range 600 ft., one target. Hit: 5 (1d8+3) piercing damage.