A villainous statblock

I have made a ... well, a villain, of sorts. He's the leader of a criminal organisation, but he's also employer who secures income (also legal income) for quite a lot of people. And he's the kind of criminal who takes care of his own.

Also, if you're a player in my campaign, this is not for you! Eyes off! :p

So Mr. Seasalt, the notorious leader of the Blessed Guild of Porters, Dockworkers and Longshoremen, is essentially a rogue. 

I play essentially no official games. I have no idea what could be like ... lair actions, or legendary actions. I'm not even sure those are the right terms.

Can you give me examples of what a boss like this could be capable of? As an aside, he already has the best of what the Rogue class would give him, Evasion, Sneak Attack, Stealth, and so on.

You can look at the extant creatures with legendary and lair actions for examples.

For legendary actions for a rogue crime boss type, I could see things like getting to move his base speed without provoking OAs. Probably making an attack.

Then something special for some real zip. Maybe calling in some allies — a couple really low CR thugs — to help. But that last one would probably use all of his legendary actions for that round. 

Or something to manipulate the terrain, like a little 5’ square fog cloud as he disappears in a puff of smoke. Or he knocks over a bunch of shipping crates to change the shape of the battlefield by basically creating a new wall while also making a new passage.

Your Crime Boss could have Trait such as Legendary Resistance, Legendary Actions, Multiattacks, Spellcasting as well as Regional Effects within the Porters, Dockworkers and Longshoremen Guildhall. I'd look at different monsters statblocks for ideas.

So there's two parts of every villain. There's the cool storyline part, which we show our players by how we describe the villain, and by how they act and how they talk, and by how the people around them are kept in line. This is the easy part, because it's all just narrative. We can make this guy up to be as cool as we want, just by how we describe how the people around him fear and obey him.  Then there's the other part, the stat block. This is where it all goes south. Because it's so disheartening when you spend months building up some criminal underworld mob boss to be the toughest guy since Tony Soprano, but then he gets floorwiped in the first round of combat. So how do we avoid that? Simple. No stat block. 

Think about what it would take to become the mob boss of a criminal underworld guild in a world where magic can do anything! In a world where invisibility, and mind control, and magical weapons, and teleportation, and undead armies are all just normal parts of your day, everyone's gonna be a little bit paranoid. But anyone in a position of power is going to be super extra double paranoid! Imagine how many opponents this person has "defeated" to become the mob boss. Imagine how many magic shops he's running a protection racket on. Imagine how many people owe him a favor. There are legends about this man, and no one knows how many of those stories are true. So why risk it?

The point is, if you give the villain a stat block, the party WILL kill him. And that will take away all the fear and mystery. If you want this villain to be an ongoing Boogeyman, don't give him a stat block. The players deal with underlings only. Every mob has a hierarchy. When my car needs a tune up, I don't bring it to the CEO of Hyundai Motors, I bring it to the lady at the service center across town. All your characters know about the mob boss are rumors. The mob boss never travels out in public wearing his own face. He wears disguises, or uses illusion magic to appear as someone else. That way, he can be everywhere and nowhere. The mob boss never has to kill anyone (any more). He gives an order to a Capo, the Capo tells the soldiers, the soldiers make the hit, and the Consigliere makes sure none of it leads back to the boss.  If somehow your players make it past all the layers of hierarchy, and see through all the illusions, and survive the constant attacks by assassins, and actually manage to come face to face with the mob boss . . . as soon as the first player hits him, he uses his reaction to activate a magic item in his pocket that teleports him to a safehouse across town. 

You can't kill something that doesn't have hit points. 

Quote from AnzioFaro >>

 

You can't kill something that doesn't have hit points. 

While I agree with everything else you mentioned, I'm thinking the OP wants a final boss fight eventually. I haven't read books for a while but, I only really remember supernatural beings and a few "legendary" characters getting much in respects to lair actions and all the other legendary abilities.

Super agree that 95% of "fighting the boss" would be dealing with flunkies and tracking down leads to actually corner him somehow. If you expect him to hold off a multi member party on his own, you better be ready to make him strong enough to PK.

He's sort of an optional enemy. Not so villianous as to require a fatal outcome. The watch commander hired the PC's to catch him - but he then hired them to catch the watch commander in turn. 

Slightly surprisingly, the PC's were able to capture him. So right now he's actually in their power. He'll get free again - I happen to have this on good authority. 

Now, he's dangerous, but even more so, he's annoying. He uses speed and stealth and minions - stuff that's already been mentioned here. But I struggle a little to come up with better rogue-like ... super powers. Smoke bombs, yea, but he already has stealth. It's like ... what I'd like is something besides what the class would grant him.

Too few rogue villains, I think. Which is ironic. 

Like, maybe he can see in magical darkness? That could be pretty powerful.

Maybe he has a double, or can create one? Like, smoke bomb, double. That fits the annoying theme.

Or a more substantial effect, like Fog Cloud - and then he can mimic one of the PC's?

If you are not innately a magic class, you pretty much need magic items to do "cool" non-conventional things. If this guy is a mover and shaker, he would have access to that.

One does not need levels in the rogue class to be rogue-like.  Plenty of magic items allow you to change your appearance, or to escape capture through teleportation or whatnot. Maybe he's a warlock with Devil's Sight, Eldritch Sight, One with Shadows, and Beguiling Influence. Maybe he's got a species advantage, like maybe he's a changeling, or maybe he has a team of changelings who he uses as body doubles. Maybe he's secretly a sorcerer who has used a combination of enchantment spells and violence to become the boss.  But the bottom line is, whatever ability you want the boss to have, they have it. NPCs aren't restricted by player character build rules. And maybe he's got a bunch of homebrew magic items. 

Maybe some teleports, like a few uses of misty step per day. Or a cape of the mountebank for a dimension door if things really go sideways for him?

Or a charm effect. The ‘24 pirates have little short term charm effects. Those can be really annoying. Or maybe his time as an authority figure has given him command not as a spell but as an ability. 

Rogue-like villain, well you have a few options. I like to give rogue-like villain some cool magic items they have stolen or "acquired" from somewhere.

For a crime lord :

• a special necklace that allows them to cast Mislead once per day,
• cufflinks that the villain can touch / throw to transform into a pair of tier-appropriate animal/monster once per week e.g. golden lions, silver dire wolves, bronze griffins, onyx displacer beasts, or platinum chimeras.
• a cloak that casts Darkness which the wearer can see through a few times per day.
• a pocket watch or bag of glitter that can cast Hypnotic Pattern.
• a tie that transforms into a giant constrictor snake or a tier-appropriate snake-like enemy.
• toy wooden doors they can spy / teleport through
• Extinguisher - some kind of device that when activated extinguishes any source of nature (non-magical) light.

For Lair actions for a crime lord you want something that mimics traps. Things like:

• Trap door opens under a PC - Dex save or fall into the basement that is full of toxic fungi the gang uses to create drugs / poisons, and which poison / suffocate anyone who disturbs them. 
• Net falls from the ceiling in a 10ft radius - Dex save or restrained.
• Poison darts shoot out of a hidden hole in the wall - Dex save or piercing + poison damage.
• Smoke / gas traps release in an area

For Legendary actions for a rogu-ish character. You could do things like this:

• Dagger-ang : throw a dagger at two different targets as the blade bounces / curves through it's arc.
• Acrobatic Strike : move up to their movement speed leaping over/under other creatures or obstacles without provoking AoO, then make an attack against one creature with advantage. 
• Dirty Trick : throw sand / salt into the eyes of another creature - the target makes a Con save or be blinded until  the end of their next turn.
• Pull the Rug : push furniture or pull on a rug to trip someone - the target makes a Dex save or falls prone.