Bookie (5e Class)

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A Dragonborn shouts in anger as the nimble halfling darts out of the casino. A quick dodge to the side allows the halfling to dodge an Axe to the head. The Dragonborn follows the halfling close behind as he nears the door. Just as the Dragonborn's axe is nearly in his back, the halfling teleports away with a puff of smoke.

Creating a Bookie[edit]

Remember when creating a Bookie, you aren't meant to be on the front lines at all times. You won't be the burliest warrior, or in the back flinging fireballs, but sneaking in the shadows like a rogue until your chance to strike arrives.

Your backstory is important to your character, so consult your DM about the setting. Are there modern casinos that your character gambles their life away in, or are there saloons scattered about that your character cheats.

Quick Build

You can make a Bookie quickly by following these suggestions. First, make Dexterity your highest ability score, followed by Charisma. Second, choose the charlatan background.

Class Features

As a Bookie you gain the following class features.

Hit Points

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


Armor: Light
Weapons: Simple, Light Crossbow
Tools: Theives' Tools, Forgery Kit
Saving Throws: Dexterity, Charisma
Skills: Pick 2 from Acrobatics, Deception, Perception, Persuasion, Sleight of Hand, and Stealth.


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

  • 2 daggers
  • (a) Leather and 2 Javelins or (b) Studded Leather and 1 Javelin
  • A light crossbow and 20 bolts
  • A Burglar's Pack
  • If you are using starting wealth, you have 2d12 x 10 in funds.

Table: The Bookie

Level Proficiency
Features Luck Points
1st +2 Pickpocket, Lucky 1 + your Charisma Modifier
2nd +2 Charming Demeanor 1 + your Charisma Modifier
3rd +2 Bookish Archetype 2 + your Charisma Modifier
4th +2 Ability Score Improvement, Ability Score Improvement 2 + your Charisma Modifier
5th +3 Phase 5 + your Charisma Modifier
6th +3 6 + your Charisma Modifier
7th +3 Archetype Feature, Improv Act 8 + your Charisma Modifier
8th +3 Ability Score Improvement, Ability Score Improvement 10 + your Charisma Modifier
9th +4 Nimble 10 + your Charisma Modifier
10th +4 12 + your Charisma Modifier
11th +4 12 + your Charisma Modifier
12th +4 Ability Score Improvement, Archetype Feature, Ability Score Improvement 14 + your Charisma Modifier
13th +5 Deck of Many Skills 14 + your Charisma Modifier
14th +5 16 + your Charisma Modifier
15th +5 16 + your Charisma Modifier
16th +5 Ability Score Improvement, Ability Score Improvement 18 + your Charisma Modifier
17th +6 Great Escape 18 + your Charisma Modifier
18th +6 Archetype Feature 19 + your Charisma Modifier
19th +6 Ability Score Improvement 19 + your Charisma Modifier
20th +6 Grand Gamble 20 + your Charisma Modifier


As a Bookie, you've gotten quite good at visually inspecting people, as well as getting your hands dirty.

To use the Pickpocket action, you must roll one Dexterity check, with one proficiency modifier added if you are proficient in either Stealth or Sleight of Hand.

On a successful roll, you may find loot determined by your DM, and steal it from them.

However, be wary when using this because others may still be able to see you elsewhere. So, be sure you're alone with the person whose pockets you're digging around in.


At Level 1, you get 1 + your Charisma Modifier of Luck Points (Additional Luck points can be added on with the Halfling Race and the Lucky Feat). You can use these Luck Points to reroll an Ability Check, Saving Roll, or Attack roll. No more than one luck point may be used on one roll.

Additionally, you can expend luck points at later levels to use certain class features.

You restore 1d4 Luck Points after a short rest (to your maximum) and 1d6 after a long rest.

Charming Demeanor[edit]

At Level 2, you may use 1 Luck Point to cast Charm Person. The Spellcasting Modifier for this is Charisma.

You also gain proficiency to Persuasion if you didn't already have it, but no Double Proficiency is gained.

Bookish Archetypes[edit]

At Level 3, you may choose from 2 Archetypes to stylize the way you play your Bookie; Card Counter and Spell Shill.

Ability Score Improvement[edit]

At Level 4, you may pick 1 ability score to put 2 points into, or 2 ability scores to put 1 point into.

You may repeat this again at Levels 8, 12, and 16.


At Level 5, you can harness some magical ability and expend the physical properties of your body.

As an action, using 4 Luck Points allows you to become untargetable and ungrappleable for 1 turn. While in this state, you cannot attack or cast spells.

Improv Act[edit]

At Level 7, you have mastered the art of Improvised Acting.

You may add half your proficiency bonus (rounded down) to any skill you are not yet proficient with.


At Level 9, you have gotten into the rhythm of escaping casinos and saloons with your head intact. Increase your movement speed by 10 feet.

Deck of Many Skills[edit]

At Level 13, you have learned many things from the swindling life of a Bookie.

Select any 4 skills and become proficient in those skills Or Select any 2 skills you are already proficient in and gain Double Proficiency in them (You add your proficiency bonus to the rolls involving those skills twice) Or Gain Advantage and Double Proficiency in any one skill you are previously proficient in.

Great Escape[edit]

At Level 17, you have learned to tap into other planes of existence for short bursts of time.

As a bonus action, expending 10 Luck Points allows you to travel through another plane, shifting yourself at most 100 feet away from your starting location. You may expend 1 Luck Point per each willing creature you bring along after that.

Grand Gamble[edit]

At Level 20, you have learned the ins and outs to gambling.

You are Double proficient in Sleight of Hand if you weren't already, and can use 2 Luck Points to instantly succeed on any Sleight of Hand check.

If you roll Initiative with no Luck Points remaining, you regain 1d12 + 5 Luck Points instantly.

Bookish Archetypes[edit]

Card Counter[edit]


At Level 3, you gain a magical card deck which you can use as a Throwing Weapon. Cards deal 1d6 slashing damage at Level 3, and have a range of (20/80). The deck is enchanted as the cards return to the deck after the user throws out another.

Additionally, you may add half your Sleight of Hand Bonus to your attack rolls using the cards.

Arcane Card Tricks

At Level 7, the Card Counter has learned to precisely throw the cards and enchant them with Arcane magic.

You may spend Luck Points to: -Full House: Deal a bonus xd4 bonus damage (1 Luck Point per d4) -Jokers: Deal a bonus 1d6 Elemental Damage (Fire, Acid, Lightning, Cold) (2 Luck Points) -Aces: Knock the target prone or disarm the target (2 Luck Points) -Weighted Deck: Deal a bonus 1d12 force damage (5 Luck Points) -Bouncing Card: A card attack now bounces to 2 other enemies within 10ft of each other (1 Luck Point)

Pick a Card

At Level 12, your card deck can be used as a random spell caster. You draw a random card from your deck.

Using the Wild Magic table located in the Sorcerer class, you cast a spell using the effect associated with the d% you roll.

Deck of Many Things

At Level 18, you may draw a card from your deck, instilled with the power of the Deck of Many Things.

Playing Card — Card:

Ace of diamonds — Vizier*

King of diamonds — Sun

Queen of diamonds — Moon

Jack of diamonds — Star

Two of diamonds — Comet*

Ace of hearts — The Fates*

King of hearts — Throne

Queen of hearts — Key

Jack of hearts — Knight

Two of hearts — Gem*

Ace of clubs — Talons*

King of clubs — The Void

Queen of clubs — Flames

Jack of clubs — Skull

Two of clubs — Idiot*

Ace of spades — Donjon*

King of spades — Ruin

Queen of spades — Euryale

Jack of spades — Rogue

Two of spades — Balance*

  • Found only in a deck with twenty-two cards

Balance: Your mind suffers a wrenching alteration, causing your Alignment to change. Lawful becomes chaotic, good becomes evil, and vice versa. If you are true neutral or unaligned, this card has no effect on you.

Comet: If you single-handedly defeat the next hostile monster or group of Monsters you encounter, you gain Experience Points enough to gain one level. Otherwise, this card has no effect.

Donjon: You disappear and become entombed in a state of suspended animation in an extradimensional Sphere. Everything you were wearing and carrying stays behind in the space you occupied when you disappeared. You remain imprisoned until you are found and removed from the Sphere. You can't be located by any Divination magic, but a wish spell can reveal the location of your prison. You draw no more cards.

Euryale: The card's medusa-like visage curses you. You take a -2 penalty on Saving Throws while cursed in this way. Only a god or the magic of The Fates card can end this curse.

The Fates: Reality's fabric unravels and spins anew, allowing you to avoid or erase one event as if it never happened. You can use the card's magic as soon as you draw the card or at any other time before you die.

Flames: A powerful devil becomes your enemy. The devil seeks your ruin and plagues your life, savoring your suffering before attempting to slay you. This enmity lasts until either you or the devil dies.

Gem: Twenty-five pieces of jewelry worth 2,000 gp each or fifty gems worth 1,000 gp each appear at your feet.

Idiot: Permanently reduce your Intelligence by 1d4 + 1 (to a minimum score of 1). You can draw one additional card beyond your declared draws.

Key: A rare or rarer Magic Weapon with which you are proficient appears in your hands. The DM chooses the weapon.

Knight: You gain the service of a 4th-level Fighter who appears in a space you choose within 30 feet of you. The Fighter is of the same race as you and serves you loyally until death, believing the fates have drawn him or her to you. You control this character.

Moon: You are granted the ability to cast the wish spell 1d3 times.

Rogue: A nonplayer character of the DM's choice becomes hostile toward you. The identity of your new enemy isn't known until the NPC or someone else reveals it. Nothing less than a wish spell or Divine Intervention can end the NPC's hostility toward you.

Ruin: All forms of Wealth that you carry or own, other than Magic Items, are lost to you. Portable property vanishes. Businesses, buildings, and land you own are lost in a way that alters reality the least. Any documentation that proves you should own something lost to this card also disappears.

Skull: You summon an avatar of death-a ghostly humanoid Skeleton clad in a tattered black robe and carrying a spectral scythe. It appears in a space of the DM's choice within 10 feet of you and attacks you, warning all others that you must win the battle alone. The avatar fights until you die or it drops to 0 Hit Points, whereupon it disappears. If anyone tries to help you, the helper summons its own avatar of death. A creature slain by an avatar of death can't be restored to life.

Star: Increase one of your Ability Scores by 2. The score can exceed 20 but can't exceed 24.

Sun: You gain 50,000 XP, and a wondrous item (which the DM determines randomly) appears in your hands.

Talons: Every magic item you wear or carry disintegrates. Artifacts in your possession aren't destroyed but do Vanish.

Throne: You gain proficiency in the Persuasion skill, and you double your proficiency bonus on checks made with that skill. In addition, you gain rightful ownership of a small keep somewhere in the world. However, the keep is currently in the hands of Monsters, which you must clear out before you can claim the keep as. yours.

Vizier: At any time you choose within one year of drawing this card, you can ask a question in meditation and mentally receive a truthful answer to that question. Besides information, the answer helps you solve a puzzling problem or other dilemma. In other words, the knowledge comes with Wisdom on how to apply it.

The Void: This black card Spells disaster. Your soul is drawn from your body and contained in an object in a place of the DM's choice. One or more powerful beings guard the place. While your soul is trapped in this way, your body is Incapacitated. A wish spell can't restore your soul, but the spell reveals the location of the object that holds it. You draw no more cards.

This feature can be used once every month, and can only be used by the Bookie.

Spell Shill[edit]


For Spellcasting, Use Eldritch Knight Spellcasting table, Spell slots, and spells and cantrips known.

Eldritch Freedom

At Level 7, select 2 spells of 1st or 2nd level. These spells can be used once at will. To regain this feature, complete a long rest.

Once the spells are selected, you cannot select anymore.

Empowered Weapon

At Level 12, you form a magical bond with a weapon of your choice, taking a 1 hour ritual to form this bond.

Once this ritual is completed, you cannot be disarmed of this weapon, and if it gets more than 30ft away from you, it magically recalls to you.

Additionally, this weapon deals an extra 2d6 of damage on a hit.

You may only have 1 bonded weapon at a time, but can bond to different weapons if the ritual is repeated with a different weapon.

Expanded Mind

At Level 18, your mind has grown and your spellcasting abilities have been enhanced.

You know all Wizard Cantrips and can learn any 4 spells from other classes. These spells do not count for your total amount of Spells Known, but do require the appropriate spell slot to cast.

Additionally, you can attack as a bonus action after using a cantrip as an action.


Multiclassing Requirements: Dexterity 14 and Charisma 14 Proficiencies: Light Armor, Simple Weapons

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