Smuggler

The transport of goods, creatures, and even people can be a lucrative business, particularly if you know how to avoid expensive import and export taxes, bridge, highway, and port tolls, and other legal requirements. Exotic poisons from far-off locales, banned or cursed magic items, and illicit drugs or bootleg liquor all fetch a high price on the black market. Thieves’ guilds, pirates, and criminal kingpins pay well to those who can avoid law enforcement when moving stolen goods, provide safe channels of communication, break associates free from jail cells or dungeons, or deliver supplies past guards. You’ve become adept at all of these things, perhaps even having developed a network of contacts as a criminal, noble, con artist, or sailor during an earlier part of your life.

Level 3: Dab-handed Dealer

You gain proficiency with vehicles (land and water) and with your choice of either the disguise kit or navigator’s tools. Moreover, when determining your carrying capacity, you are considered one size category larger than your actual size.

Starting at this level, you also have advantage on Dexterity (Sleight of Hand) checks to hide objects on vehicles, and you can use the bonus action granted by your Cunning Action to make a check to control a vehicle, or to make a Dexterity (Sleight of Hand) check to conceal a light weapon on yourself, opposed by the Wisdom (Perception) checks of creatures within 5 feet of you; if you succeed on a check to conceal a weapon in this way, then you have advantage on your next attack against one of those creatures using that weapon, including on ranged attacks even if the target is within 5 feet of you.

Level 3: Smuggler's Legerdemain

Having made a careful study of laws and those who enforce them, you’ve become adept at avoiding both, even mastering a handful of arcane techniques that aid your smuggling activities. You learn two cantrips at this level and, when you reach 7th level in this class, one 1st-level spell of your choice. The cantrips and spell must be from among the illusion or transmutation spells on the wizard spell list, all of which are ideally suited for manipulating goods, duping guards, communicating with covert contacts, or escaping from a failed heist. Having learned these forms of magic through research and rote memorization, Intelligence is your spellcasting ability for these spells.

You can cast the cantrips at will and the spell once at its lowest level; you must finish a long rest before casting the spell again in this way. You can also cast the spell using any spell slots you have.

Whenever you gain a level in this class, you can replace the 1st-level spell with another 1st-level spell of your choice from among the illusion or transmutation spells on the wizard spell list.

Level 9: Hypervigilance

You have advantage on Wisdom (Perception) checks that rely on sight or hearing, and you can’t be surprised while you are conscious. In addition, you have developed an awareness for avoiding social or legal entrapment, and you have advantage on Intelligence (Investigation) checks to discern loopholes and traps in legal documents and on Wisdom (Insight) checks to discern when you are being manipulated into a bad social or legal situation.

Level 13: Improved Smuggler's Legerdemain

To further facilitate your extralegal activities, you learn a second illusion or transmutation spell, which must be one of the following: arcanist’s magic aura, blur, darkvision, enlarge/reduce, invisibility, knock, levitate, magic mouth, mirror image, rope trick, or spider climb. Intelligence is again your spellcasting ability for this spell. You can cast this spell once at its lowest level and must finish a long rest before you can cast it again in this way. You can also cast the spell using any spell slots you have of 2nd-level or higher. Whenever you gain a level in this class, you can replace a spell from this list with another from this list.

In addition, beginning at 13th level, whenever you cast one of your 1st-level Smuggler’s Legerdemain spells, you always cast it as if using a 2nd-level spell slot unless you choose to cast it using a spell slot you have of a different level.

Level 17: Slippery as an Eel

You have become especially adept at slipping away from the authorities and getting a jump on foes, even when encumbered by illicit goods. Your speed increases by 10 feet, you ignore difficult terrain, and you have advantage on initiative rolls.