Ruler

These heroes think they are powerful when they cast spells, swing weapons and use their artifacts. Fools! True power lies in control over others. Powerful the one that doesn't have to fight himself, but let others fight for him.

  • Lord Mariyan Redcastle, Ruler of the Southern Realms

Great Influencer

Rulers shine in their ability to influence other beings. By their overwhelming charisma and rhetorical abilities, they manage to find minions almost anywhere. People tend to follow and obey them almost automatically. They quickly become powerful figures wherever they settle. As great dealmakers, they hold the ability to forge agreements, alliances, and contracts fast and convincing. They gain the loyalty of the common folk, may it be by social kindness or through assertive order. By good or evil charisma they inspire and encourage, or fear and intimidate. Either way their success in achieving their goals stays unmatched Also, rulers have a strange connection to the magical forces. Whilst they not able to focus them quite as structured and efficient as other spellcasters, they're still able to cast, or rather imitate, certain spells and use them to their will.

Rulers Throughout the Multiverse

Rulers are found everywhere in the DnD multiverse, from kings and mighty politicians to guild leaders, merchants, judges, captains, majors, and interdimensional demon lords. While often adapting the abilities of other classes as well, their true power doesn't lie in their own ability to fight or use magic. It rather comes with the strategic coordination of their troops, their decisive shout calling or their social, political or economic influence. Whilst a mafia boss might be a quite good gunslinger, he's far more dangerous through his influence on the local politics and the loyalty of his minions. While a General might be a great fighter, his experience in the war strategies makes him a far greater threat.

Knowledge is Power

Additionally to their power over others, the ability to find out secrets and using the information to their advantage makes rulers as dangerous and powerful as they are. May it is through brutal torture or through empathic conversation, rulers tend to get the answers they were looking for and know instinctively how this information could come to use. On the other hand, they are great secret-keepers themselves, rarely showing any expression of their emotions or their thoughts, making them incredibly hard to read.

Creating a Ruler

Rulers can arise from any kind of background. Maybe they're the child of a powerful family and inherit their rulership. Maybe they grew up in wretched conditions, looking for might and power to forget their past. Rulers often experienced some kind of tragedy or drastic event, shaping their personality and waking their ambition. An evil ruler might have its family killed and know strives for revenge, ignoring the damage it inflicts on the way. A good ruler might experience the same but converted the sadness into love, rather than hate, becoming altruistic and caring. A crucial decision in ruler creation is the alignment. It not only influences some of your leadership features, but it also decides, which kind of minions you can acquire. When creating your rulers' personality, think of how it achieves its goals and how his social superiority manifests. Is it a frighting figure that intimidates its followers and receives loyalty through fear? Or it's maybe a selfless hero, that's a moral example and is admired by its squires?

Class Features

As a Ruler, you gain the following class features

Hit Points


  • Hit Dice: 1d8 per Ruler level
  • Hit Points at 1st Level: 8 + your Constitution modifier
  • Hit Points at Higher Levels: 1d8 (or 5) + your Constitution modifier per Ruler level after 1st

Proficiencies


  • Armor: light
  • Weapons: Simple weapons, Crossbows, Longswords, Rapiers, Shortswords
  • Tools: none

  • Saving Throws: Intelligence, Charisma
  • Skills: persuasion, deception, choose one of insight, history, religion, arcana, intimidation, performace

Equipment

You start with the following equipment, in addition to the equipment granted by your background:

  • (a) a rapier (b) a longsword or (c) any simple weapon
  • a ruler's arcane focus:
    (a) a monoclev, (b) a quill, (c) a ring, (d) a crown, (e) a scepter or (f) any other ruler's arcane focus
  • a diplomats pack
  • robes and a dagger

Spellcasting

You are able to bend reality to your will in certain ways. Your spells are part of your order giving nature, magic that you can command as you wish. See Spells Rules for the general rules of spellcasting and the section below for the ruler spell list.

The Ruler Table

Level Proficiency Bonus Features max. squire CR Command Slots Cantrips Known Spells Known 1st 2nd 3rd 4th 5th 6th 7th 8th 9th
1st +2 Impressive Charisma - - 2 3 2 -
2nd +2 Squire 1/8 - 2 4 3 -
3rd +2 Aligned Leadership 1/8 - 2 5 3 1
4th +2 Ability Score Improvement 1/4 - 3 5 4 2
5th +3 Decisive Commands 1/4 2 3 6 4 2 1
6th +3 Leadership Feature 1/2 2 3 6 4 2 2
7th +3 Additional Command, Strategic Mind 1/2 3 3 7 4 2 2 1
8th +3 Ability Score Improvement 1 3 3 7 4 3 3 1
9th +4 Additional Squire 1 4 3 8 4 3 3 1 1
10th +4 Leadership Feature 2 4 4 8 4 3 3 2 1
11th +4 Improved Commands, Additional Command 2 5 4 9 4 3 3 2 1 1 -
12th +4 Ability Score Improvement 3 5 4 9 4 3 3 3 2 1
13th +5 Will of Vengeance 3 5 4 10 4 3 3 3 2 1 1
14th +5 Leadership Feature 4 6 4 10 4 3 3 3 2 1 1
15th +5 Mighty Voice,
Additional Commmand
4 6 4 11 4 3 3 3 2 1 1 1
16th +5 Ability Score Improvement 5 6 4 11 4 3 3 3 2 2 1 1
17th +6 Third Squire 5 7 4 12 4 3 3 3 2 2 1 1 1
18th +6 Perfected Commands 6 7 4 13 4 3 3 3 2 2 1 1 1
19th +6 Ability Score Improvement 6 7 4 13 4 3 3 3 3 2 1 1 1
20th +6 Unquistioned Authority 7 8 4 14 4 3 3 3 3 2 2 1 1

Spell Slots

The Ruler table shows how many spell slots you have to cast your Ruler spells of 1st level and higher. To cast one of these spells, you must expend a slot of the spell’s level or higher. You regain all expended spell slots when you finish a long rest. For example, if you know the 1st-level spell heroism and have a 1st-level and a 2nd-level spell slot available, you can cast heroism using either slot.

Spells known of 1st level and higher

You know three 1st-level spells of your choice from the ruler spell list. The Spells Known column of the ruler table shows when you learn more ruler spells of your choice. Each of these spells must be of a level for which you have spell slots, as shown on the table. For instance, when you reach 3rd level in this class, you can learn one new spell of 1st or 2nd level.

Spellcasting ability

Charisma is your spellcasting ability for your ruler spells. Your magic comes from the heart and soul transported by your mighty appearance and social domination. You use your Charisma whenever a spell refers to your spellcasting ability. In addition, you use your Charisma modifier when setting the saving throw DC for a ruler spell you cast and when making an attack roll with one. Spell save DC = 8 + your proficiency bonus + your Charisma modifier Spell attack modifier = your proficiency bonus + your Charisma modifier

Ritual Casting

You can cast any ruler spell you know as a ritual if that spell has the ritual tag.

Spellcasting Focus

You can use, a monocle, a quill, a ring, a crown, a scepter, or any other item that consolidates your social power (such as the hat of a captain, etc).

Impressive Charisma

Your rhetorical and social skills are exceptional. Engaging in a conversation, you intuitively assume the goals and morales of your person opposite, finding the right words to appeal to them.
Starting at 1st level, when doing a charisma check that involves (exactly) one other humanoid, you can guess the alignment of your person opposite. If you guessed correctly you gain advantage on the check. One example of how that could happen:

Maryian Redcastle, a noble knight from the southern realms, is trying to convince the guards to let him and his party pass without being searched because they need to get to the king as quick as possible. (Correctly) predicting the guard he's talking to is lawful neutral, he applies to the urgency of the situation and gains advantage on the persuasion check


Squire

Starting at 2nd level, you can acquire one NPC as a loyal servant, an acolyte or a squire. In agreement with the DM, you can choose this NPC as you wish, provided that they have the same alignment as you or an adjacent one (see the Leadership Table). You might also have to take certain steps in order to achieve the squire's trust. Often a conversation is enough, but depending on the situation, further steps could be needed. It can be a humanoid of challenge rating 1 or lower. This squire is controlled by the DM, but obeys your commands and tries to complete the tasks you give it to his best ability if it does not critically contradict with his goals.

At higher levels the possible challenge rating of your squire increases, as well as the number of squires you can have at the same time. As stat blocks for your squire, you can look into the humanoid list or come up with your own stat blocks. You can also create a PC-like character. In this case, your maximum (combined) squire level is your ruler level divided by two (round up). 1*

Aligned Leadership

Your alignment shapes your values and morals which are crucial concerning your leading ability and the target group of your social influence. Beginning on 3rd level, you choose one Leadership type. You can choose the one that matches your alignment, or one next to that in the table below. For example, if you are chaotic neutral, you can choose between the Villian, the Captain, or the Rebel Leadership.

Your Leadership Type heavily impacts the way you interact with your squire(s), your companions and other people. It shapes your personality and the way you use your power.

Your choice grants you features when you choose it at 3rd level and again at 6th, 10th, and 14th level.

Ability Score Improvements

When you reach the 4th level, and again at 8th, 12th, 16th, and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can’t increase an ability score above 20 using this feature. Using the optional feats rule, you can forgo taking this feature to take a feat of your choice instead. Look into feats for more information.

Alignment Table

Evil Neutral/True Good
Lawful
Neutral/True
Chaotic

Decisive Commands

Starting at 5th level, you get the ability to shout strategic battle orders to incline your squire and your companions to achieve a certain goal in combat. Getting encouraged, inspired or frightened by your presence, anyway, your minions immediately follow them. Your companions, as well as your squires, that are in sight, can hear you and are in 100ft. range, gain benefits depending on the command. The effect of the command lasts until your next turn.

Command Slots
You have 2 command slots, and you gain more as you reach higher levels, as shown in the command slots column of the Ruler table. You can never have more command slots than shown on the table for your level. You regain all spent command slots when you finish a long rest.

At 5th level, you can choose 2 Commands from the following list. You can Choose additional Commands at 7th, 11th, and 15th level

Focus

By shouting this command you point to an enemy, inclining your companions to concentrate on that target. They get +2 on attack rolls against this target.


Protect

You point to an ally, inclining your companions to protect it. If the target has 2 allies in 5ft. range of itself, it gains +2 AC.

Attack

You incline one of your companions to attack viciously. When the target takes the attack action on its turn, it can make an additional one afterward.

Heal

You encourage your companions to restore the health of a wounded ally. The first healing this target receives ally is maximized.

Revive

You point to an unconscious companion and guide one conscious ally to revive the fallen one. When this companion tries to stabilize the target, it gains proficiency with the medicine check. This benefit ends, when the target becomes stable, or at the start of your next turn.

Dodge

With this command you assume an enemy spellcaster to cast an area of effect spell. The next time one or more of your companions has to make a dexterity saving throw to avoid a spell that deals damage, they only take half damage on a failed throw and 0 damage on a successful one.

Strategic Mind

Beginning at 7th level, your mind adapts to events around you, connecting different plots and getting a better overview of the complexity of the world. You can quickly analyze situations and make out the correct reaction. You get the keen mind feat.

Additional Squire

Begninning at 9th level, you can promote an additional squire into your togetherness. Note, that the max. CR of your squire in the ruler table shows the combined maximum CR of all your squires. For example, at 10th level, you can have one squire with a CR of 2 or two with a CR of 1.

Improved Commands

On 11th level, your commands grow in power, inspiring your allies even more and lead them to success in battle.

  • The Focus command instead gives +3 on attack rolls against the target.
  • The 'Protect' command instead increases the AC by +3.
  • The Attack command provides extra attacks for up to two allies, rather than one.
  • The Heal command maximizes up to 2 healing spells on one target or 1 healing spell each on two different targets.
  • The Revive When the target is stabilized by an ally, it not only gains proficiency on the roll, it also does the roll with advantage.
  • The Dodge All allies in range do the next dexterity saving throw with advantage and take half damage on a failure, and no damage on a success.

Will of Vengeance

You feel to be chosen for a greater destiny. An exposable minion or a loyal soldier might fall in battle, but not a leader like you. If you fall unconscious and are dying your inner will of vengeance awakes and bounds you to live until you achieve your goal. Starting at Level 13, once per long rest, when dropping to 0 hit points you can choose to use this feature. You can add your proficiency bonus to all death saving throws. This benefit only lasts until you become stable, regain hit points or finally die. Note, that you need to decide whether to use this feature before the first roll on the death saving throws.

Mighty Voice

Beginning at 15th level, your commands can be heard over vast distances and let your enemies hesitate while encouraging your allies even further. The range of your commands increases to 200ft.

Third Squire

Begninning at 17th level, you can promote a third squire into your togetherness. Note, that the max. CR of your squire in the ruler table shows the combined maximum CR of all your squires.


Perfected Commands

On 18th level, your commands improve even further, making them battle deciding moves.

  • The Focus command gives +4 on attack rolls against the target.
  • The Protect command increases the AC by +4.
  • The Attack command provides extra attacks for up to three allies.
  • The Heal command maximizes 3 healing spells on up to three targets.
  • The Revive command lets the target become stable immediately after one medicine check succeeds. Also, the throws have advantage and are made with proficiency.
  • The Dodge command lets up to three targets automatically succeed on the dexterity saving throw. All other allies in range make the next dexterity saving throw with advantage and take half damage on a failure, and no damage on a success.

Unquestioned Authority

Reaching Level 20, noone dares to speak up to you, apply to your moral or mess with your values. Your goals are set and clear and nothing will even scratch your will.
You automatically succeed all charisma saving throws.

Subclass Options

Tyrant - Lawful Evil

Tyrants are powerful leaders, with great social,
economic or political influence. They work within an established system and rule over their people with great dominance and strictness. Although, they think about their own benefits first, before considering others, if they ever do so. All their actions aim at gaining more power or preserving their current. Squires of tyrants follow them, because they fear punishment or because their alternatives are even worse than the cruelty of their ruler.

Fearsome Presence

Beginning on 3rd level, you're surrounded by an aura of grimness, causing all others to tremble when they witness you. You gain proficiency in intimidation checks. If you are already proficient, you gain expertise.

Exposable Minons

You can gather a vast number of squires, forming a fellowship around yourself. However, this gang of insignificant servants can't include any stronger fighters.
Starting at level 6, you can have up to 10 Squires, but only two of them can be of CR 0. To better structure combats, some of them might by summarized into swarm-like statblocks.

Tactical Retreat

Starting on 10th level, you have the ability to quickly hide behind your line of minions in order to coordinate the battle from a safe position, without being endangered. Once per short rest, if you take damage, you can use your reaction to disengage and move up to 15ft. This amount increases to 25ft. when you move towards one of your squires.

Word of Supremacy

On 14th level, you get the ability to shout a war cry onto the battlefield and thusly horror your enemies into paralysis. You gain the following commands, which use up two command slots each:
Tremble:
You can choose up to six enemies. They have to succeed on a CHA saving throw against your spell save DC or be frightened by you for 120 seconds.


Shiver:
The four nearest enemies to you have to succeed on a CHA saving throw against your spell save DC or be paralyzed until the end of their next turn.

General - True Lawful

Generals are the aspect of justice. Often experienced in war, their one and only goal is to preserve the social system they consider best for their realm. As great leaders and brilliant minds, they worked themselves up from a front-row soldier to the decision-maker behind the lines. Generals shine in their ability to encourage and empower their battalion in order to defeat forces they consider hostile. From their squires, they expect high loyalty, which is delivered, most of the time, by a feeling of justice or faithfulness.

Accomplished in War

When you choose this leadership type at 3rd level, you gain proficiency with cartographers tools, land vehicles and martial weapons.

Strategic Positioning

On 3rd level, you gain the ability to locate yourself decisively at the beginning of a combat. On Initiative 25, you can walk 25ft. regardless of where your normal turn is positioned. Use can use this feature only in the first round and only once per short rest.

Commander

In your military education and in your practice in war, you learned how to order a party to increase their chances of victory critically. Beginning 6th level, Your command slots increase by +2.

Last Stand

On 14th level, you are able to channel your will of victory in the most desperate situations and strike a major blow against an enemy. You can use this feature only when two or more allied PCs (including your squire) fell unconscious during the battle and are dying. Your next melee attack hast +10 to hit and deals 200 radiant damage that can't be reduced by immunities or resistances. You need to finish 50 long rests to recharge this feature.

It was in this moment, when all hope had faded, that [the] son of the king, took up his fathers sword.
— J. R. R. Tolkien

Hero - Lawful Good

The Hero is the classic good guy ruler. He's following the law and brings order, as well as righteousness and justice. He supports the poor and the weak and fights for those who cannot. As a consequence, he's loved by the folk and admired throughout the land. Those who serve the established social system are willing to help heroes, hoping to contribute to their public status.

Downbringer of the dark

When you chose this feature at 3rd level, you gain darkvision in a 60ft. range. If you already have darkvision the range increases by 60ft.


Solemn Fighter

On 3rd level, you gain proficiency with medium and heavy armor as well as shields.

Defensive Commands

Starting at 3rd level, you learn to encourage and inspire your companions through the bear sound of your voice, allowing you to cast the Shield of Faith spell or the Sanctuary spell using a command slot instead of a spell slot. Additionally, you can expend spell slot of 2nd level, or higher, or two 1st level spell slots, to regain a command slot.

Mercyful Regret

Ture heros do not ask anyone to follow them. Although people tend to do so anyway. Heros suffer greatly at the loss of those they swore to protect.
Starting at 3rd level, whenever you see an allied PC or squire die, you must succed on a WIS saving throw. The DC depends on the relationship to the deceased and the cruelty of their death. If you fail, you suffer one level of exhaustion for one week and can't aquire a new squire for the duration.

Frotnrunner

When you reach level 6, you become an example of battling at the front. Your allies have their movement increased by 5ft. while tmoving towards you. Also, enemies have their movement reduced by 5ft. when moving away from you.

Heroic Intervention

At 10th level, you are able to quickly stand by an ally that has been hurt in battle. When an ally loses more than 15 hit points at once, you can use your reaction to move up to 30ft. towards him and cast cure wounds as a 3rd level spell without using a spell slot. You can't use this feature again until finishing a short or long rest.

Majesty

At 14th level, you become the embodiment of elegance and grace. When a humanoid of the opposite sex sees you for the first time, there's a 20% chance he or she falls in love with you. When you kill a monster with a challenge rating of 10 or higher, everyone who sees that has to repeat that roll. You are not informed which NPC falls in love with you, and the DM decides to what extent the love occurs.

Benefactor - True Good

Benefactors thrive in goodwill. They try to do best to their people, regardless of the status quo or their own social status or the rules established in the political system. Often, people not only look up to benefactors but are fundamentally dependant on their kindness, loving them for what they did and supporting them with borderless loyalty.

Kind Donation

Beginning on 3rd level, You can improve your social status by donating to those in need. These people include beggars, priests and other clerics, poor families, orphans and all those who might ask you for a donation. By that, you slowly increase your reputation of this specific settlement. When you consistently donated you could gain the following benefits:

  • A shopkeeper might gift an item to you
  • A police officer might free one of your imprisoned companions
  • A smith or another tradesman might craft you something for free
  • A traveler might approach you with interesting news from another town
  • A scholar might come forth and tell you some of its new findings
  • A cleric might bless you with the power of his diety There are many other minor benefits you can receive when donating. The DM decides what these could be.

Rejuvinating Presence

Starting on 3rd level, your mere presence
provides calm and relaxing vibes, allowing
you to refresh faster. You can finish a short
rest in half an hour. Also when you use
half an hour to nourish your
companions while they take a short
rest, they get an additional hit dice for free.

Graceful Commands

Beginning at level 6, you learn to
restore the life of your companions
through the encouraging sound of
your voice, allowing you to cast the
Mass Healing Word spell or the
Prayer of Healing spell using a commanding charge. Additionally, you can convert a 2nd level, or higher, or two 1st level spell slots, to regain a commanding charge.

Everlasting Loyalty

Starting at 10th level, your Squires become extremely loyal to you. You gain control over your squires. Also, your squires now do death saving throws, as PCs would. You can attune up to one magic item to each squire, provided that the class requirements are met. When you leave your squire behind to pick up a new one, the former squire stays in touch to you, ready to get back into your companionship some later day.

Cleasing Adjucation

On 14th level, you can channel your well-meaning authority to shield you and your allies from harm for a brief moment. Once per long rest, you can use this feature as an action. Speaking out this order of abjuration, all allies in 120ft. range are cleansed from all their conditions and become stable if unconscious. Until the start of your next turn, if any ally would drop to 0 hit points, they drop to 1 instead.

Rebel - Chaotic Good

Freedom and for those who are suppressed! Down with the Tyrants that subdue our people. Rebels fight for a good cause, often an injustice of the current system or another strong individual, that oppresses the defenceless. While their goal might be a noble one, rebels tend to take extreme actions in order to free their people. Overthrowing an entire system is tolerated when it leads to a change of power.

Squires of rebels often follow them willingly, without being incited by the rebel himself, who doesn't hold much with rulership.

Survivalist

When you choose this leadership type at 3rd level, you gain proficiency in the nature and survival skills, if you don't already have it. Your proficiency bonus is doubled for any ability check you make that uses either of those proficiencies.

Fighting for Good

At 3rd level, you gain proficiency with martial weapons, shields, medium armor, and land vehicles.

Disobedience

Starting at 3rd level, the relation to your squire becomes rather a loos partnership, than a hierarchical order. While the squire might follow you and your party around and his goals are roughly the same as

yours, he does not follow your command as strict as he would follow other leader's commands. The DM decides to what extent this feature applies. 3*

Managing Poverty

On 6th level, you're able to improve the living conditions of every poor humanoid, by spending time and effort. In any settlement, you can spend up to 3 hours per day to help humanoids with poor or lower lifestyles. Roll a d6 and per hour to see how many people you can help. Roll a d10.On 1-3 you manage to increase their lifestyle up to squalid, on 4-7 up to poor, on 8-9 up to modest and on 10 up to comfortable.

To thank you for your service, you can gain the following benefits:

  • A shopkeeper might gift an item to you
  • A police officer might free one of your imprisoned companions
  • A smith or another tradesman might craft you something for free
  • A traveller might approach you with interesting news from another town
  • A scholar might come forth and tell you some of its new findings
  • A cleric might bless you with the power of his diety
  • There are many other minor benefits you can receive when you helped people. The DM decides what these could be.

Ambush

On 6th level, you get advantage on stealth checks. Also, you can use a command slot, to give up to six allies advantage on their stealth checks as a bonus action. If you take the attack action during a surprise round, you can make an extra attack.

Torches and Pitchforks

On 10th level, you can acquire the support of a town's population, motivating farmers to take what they have and fight alongside with you. In a village where youmanaged poverty of at least 30 people, you can use this feature, to gain the support of 3d20 Commoners for a particular task that can be completed within one day. These people follow you around and also obey your commands if it's obvious that the command works toward completing the task (if you won them for building a house, and you command them to fight something, they probably disobey). You can use this feature only once per town.

Charismatic Conversion

On 14th level, you gain the ability to change the view of people around you, appealing to their humanity and will of freedom and thereby changing their alignment. When you talk to an NPC, you can try to convert them. You need one minute for this, when in combat and ten minutesm when not in combat. In order to convert them, you can make them do 'charisma death saving throws' against your spell save DC. A creature is immune to the charmed condition automatically succeeds this throw. If you or an ally is in combat with them, they do the save with advantage and you have to spend your bonus action to keep the conversation going. If they reach 3 failures, they are converted, changing their alignment (permanently) to chaotic good and causing them to be charmed by you for one hour.


If they reach 3 successes, they avoid your conversion and you can't attempt to convert them again.

Captain - True Chaotic

Feared by every noble and every merchant, captains roam a region, breaking the law, enriching themselves and staying under the radar of the police forces. At sea, they're called pirates, on land bandits and in city thieves. Wherever they consider their territory, it's dangerous land for those who don't know how to defend themselves. Some of these outlaws stand out as particularly vicious and ruthless and naturally become the leader of their gang, the Captain.

Lawless Domain

When you choose this leadership type at 3rd level, you can choose a square area of up to 16 square miles. You must have spend at least one week inside this area. Inside it, You gain the following benefits:

  • Difficult terrain doesn’t slow your group’s travel.
  • Your can’t become lost except by magical means.
  • Even when you are engaged in another activity while travelling (such as foraging, navigating, or tracking), you remain alert to danger.
  • If you are travelling alone, you can move stealthily at a normal pace.
  • When you forage, you find twice as much food as you normally would.
  • While tracking other creatures, you also learn their exact number, their sizes, and how long ago they passed through the area.

You can choose a new domain every 7 days. The size of the area increases at 9th level to 36 square miles, at 14th level, to 81 square miles, and at 20th level to 225 square miles.

Skilled Fighter

Beginning on 3rd level, you profit from you skirmishing experience. You can use the Disengage and the Dash action as a bonus action.

Greed

As an experienced thief, your ability to assume the worth of items and locate valuable objects is outstanding. Beginning on 6th level, you gain advantage on insight, arcana, and investigation checks, when you try to find out the worth or location of valuable or magic items.

Duel of the Captains

Starting on 10th level, you thrive in
one to one fights, focussing on one opponent
and cut out anything else to empower your
strikes. In combat, when you attack a creature
that is within 5ft. range of you and no other creature
is within 15ft. range of either of you, you can use the attack action as a bonus action and gain a +2 bonus to your attack rolls.

Back Against the Wall

Beginning on 14th, you gain the ability to fight yourself out of even the most desperate situations. If at least two enemies are within 10ft. range of you, you can use this feature as an action. You can walk up to 30ft. straight into one direction, without provoking opportunity attacks. Also, you can attack every enemy you pass, provided they are in your melee range at some point. You can use this feature only once per long rest.

Villain - Chaotic Evil

Noone kills more ruthless and destroys more efficient than the big bad guy. He or she is the leader of a dark force, an army of banished people that aim for revenge against the kingdom or the head of an underground organization, a long searched criminal with a huge bounty that's planning out his destruction of the world as we know it. Villains are cruel and brutal in their actions and fear no measure to achieve their goal.

Playing a Villain

Villains are evil. That lies within their nature. However, when a player chooses to be a villain, they also want to play and influence the game and its story in a positive way as every player does. In order to achieve this goal, you have to come up with a clever solution to fit the goals of the character with those of the party. Maybe the villain is disguised as a mercenary. Maybe he was defeated but managed to flee and now again builds up his power in order to strike later. Maybe he was a villain in a different land, decided to give up his evil plans and now fights for good. It might seem challenging in the first place to actually create a coherent character of this subclass, but playing a (semi-) evil character can also be a lot of fun.

Figure of the Underworld

As a villain, you interact with other criminals on a regular basis. When you choose this leadership type at 3rd level, you learn undercommon or another language if you already know it. Also, you gain expertise in the Intimidation and Insight skills.

Known by Evil

At 3rd level, you choose a symbol of your wickedness. This can be your arcane focus but does not have to. Once per long rest, you can present this symbol. All undead, demons, devils, aberrations, and creatures with evil alignment have to succeed on an INT saving throw against your spell DC or be charmed by you for 1 minute. Other creatures can make an INT (religion) check against your spell save DC to learn that this is a symbol of evilness.

Dark Fellowship

Beginning at 6th level, you can recruit
creatures of the shadow to follow you in your evil
allegiance. When you receive this feature, you choose one monster type except humanoid, ooze and celestial. Your squires can also have the chosen type.

Sacraficial Minions

Starting at 10th level, you can drain the life from your minions to heal yourself. You can use a command slot to, as a bonus action, make one of your minions cast the Life Transference spell on you. They don't have to use a spell slot or be able to cast this spell normally. You choose the level at which they cast it up to your maximum spell level.

Patreon from the Void

At 14th level, You can channel your evil energy to call upon the nine hells and release a shadow from the darkness. You can take an action to cast the Summon Greater Demon spell at your maximum spell level. You can increase the challenge rating of the summoned demon by sacrificing your squires. As their life essence is drained and fueled into the void, the challenge rating increases by an amount equal to the combined challenge rating of all squires sacrificed. You can use this feature only once per long rest.

Schemer - True Evil

Who hides in the shadows, overseen by the just who are blinded by naiveness and distracted by honor. Those who forge evil plans, craft hideous contracts and blackmailing their enemies into helplessness. The heads of secret underground organizations who stay hidden from the powers of righteousness, we call them schemers. They are the wicked minds that thrive on the strategic destruction of villages, towns cities, and even countries and entire social systems.

Playing a Schemer

Schemers are evil. That lies within their nature. However, when a player chooses to be a schemer and therefore playing with an evil alignment, they also want to play and influence the game and its story in a positive way as every player does. In order to achieve this goal, you have to come up with a clever solution to fit the goals of the character with those of the party. Maybe the schemer fights against an even greater evil that stayed unnoticed, tolerating sacrifices in order to protect the world and thereby seeming evil only in the first place? It might seem challenging in the first place to actually create a coherent character of this subclass, but playing a (semi-) evil character can also be a lot of fun.

Mastermind

When you choose this leadership type at 3rd level, your intelligence score is increased by +1. Also, you gain proficiency in the cartographer's tools.

Lie Identifyer

Beginning on 3rd level, you spot lies told by others more easily and precisely than others would. Your passive insight increases by +5.

Vicious Contract

Starting on 6th level, contracts made with you hold a magic power that originates from your wicked authority. You can use a casual quill, paper, and inc. Only the sign of your contract partner has to be made with blood or magic inc. You have to word the contract precisely and best write it down word by word. Because once you and the contract partner signs willingly, the contract can't be broken. The magic of the contract binds you both to obey it, even if you don't want to. When you act directly against the contract you suffer increasing levels of exhaustion and ultimately die. The contract, however, ends immediately when either of the contract partners dies or when both of you
agree on ending the contract and shaking
hands to confirm it. The 'curse' of the
contract can also be removed
by the Wish spell.


Strategic Foresight

Starting at 10th level, you can foresee the outcome of a linear combination of actions. Your great mental abilities allow you to calculate to a percentage precise chance how likely a certain row of events will be. Once per long rest you can use this feature as an action using one of your command slots. You imagine up to three actions or events that could happen in the future. In a flash, you receive a vision of the future that comes into existence, when your named actions actually happen. You could also receive multiple scenarios and a percentage, how likely each of these possible futures is.

Blackmail

On 14th level, you gain the ability to find out the deepest and darkest secret of someone just by looking at him. You can use this ability to force someone into blackmail, changing his primary goal to do whatever he can to not have his secret revealed by you. You can use this feature by looking at a humanoid target for at least a minute. If you're in combat with the target, you have to concentrate on it for the duration. Afterwards, you can start talking to the target, dropping hints that you know this one thing about it and that you will crush its life if it does not obey your will. If you do so, using a bonus action in combat, the target starts to make 'charisma death saving throws' against your spell save DC on its turns. Creatures with immunity to the charmed condition automatically succeed. You have to keep talking to the target, keeping up concentration. When the concentration is broken early, the target automatically succeeds all saving throws concerning this feature. The feature can't be used again until you finish a short rest and the target stays immune to it for a year. When the target reaches three failures he gives in to the blackmail and obeys your commands, being charmed by you until the cause of the blackmail is removed. Others can find out about the blackmail doing wisdom (insight) checks against your spell save DC while studying the target. Should the target reach 3 successes first, it withstands the blackmail and won't be scared into obedience. However, the information remains and you can still use it to damage the target otherwise. In both cases, you can't use this feature
until you finish the 7th short
rest after using it.

Cantrips (0 Level)
Cantrips (1st Level)
2nd Level
3rd Level
4th Level
5th Level
6th Level
7th Level
8th Level
9th Level

Appendix A - Footnotes & Comments

Is this even Role Play?

So, maybe, after reading this class you ask yourself why I included so many features and traits, that are cool, but can be accomplished by role play, without having it written down in a rule. Some might even argue that this takes away the challenge and the fun of social interaction and socially challanging situations. I see it this way: The rule book of DnD at numerous points offers stats and rules for something that can just be described. Take the shove action for example. However you could just use the improvise action to describe that you tackle your enemy and the DM comes up with the rule setting (contested strength check and so forth). However, there is a specific rule for shoving to improve its usabilty and justification and also inspire the players.
Similarily, by creating this class, I am trying to inspire players to really go to town on social interactions and use the ruler features to live their dreams as a powerful commander. And yes, I am still creating, changing, fixing. I would love to hear your feedback and playtest experience!

1 - Squires

So this mechanic is not new to DnD. When it comes to the animal companions of rangers or summoned creatures of certain spells, the rules cover the management of entites pretty well. However the squire mechanic focuses on humanoid NPCs which is inherintly a new thing. Who ends up controlling the squire is obviously negotiable. Like any other NPC, you might agree that the player(s) get to control their squires, even without choosing the Benefactor subclass. Some DMs might have already included that mechanic without needing a class like the ruler to apply any ability. However, being an ally, friend or companion to the party, and being a squire, or rather a disciple to one partymember, is different. It is fun to roleplay the hierachy that is created here. Also: Whereas the squire has to align with the ruler, it does not have to comply with the other party members. Keep those things in mind, when (role)playing these special NPCs.

2 - Falling in Love

Yet another example of a rule, that normally would have naturally occured through role play. Statwise you might assume this feature would be rather overpowered. I concur. Just because a NPC is in love with you, they don't sacrifice everything they have to obey you. The DM can decide, whether this feature manifests as a mere crush, a sexual approach or selfless love after all. However, you too can be creative about what advantages you construct from it. I am looking forward to the stories that emerge from this feature!

3 - Disobedience

I suggest you find a common approach to this before actually playing it out. For example, you can roll, if the rebel issues a major order, and with a 10% chance the squire doesn't follow. Or you could just make up your own goals for the squire and let it disobey if the commands slightly contradict these goals.