Help with balancing my party

As mentioned above, check the math and the character sheet. Try to build this Assassin yourself from scratch. If you can't do it - even knowing the desired goal - sit down away-from-table and have a talk: how did HE do it?

When I ran Arauthator in Rise of Tiamat, I amped him up as high as I could within the rules: he became an Ancient White Dragon (not Adult), with max HP &c. The Ranger still got a crit with an Arrow of Dragon Slaying and took out 1/5 of his total HP in one shot. I didn't have to act very much when I started wheezing and choking and holding my ribcage.

Assassins have to set up an ambush to get all their cool features to work right. Is that what your group is doing, or are they kicking down the monsters' front door?

If the group is making a name for themselves, have some NPC Rogue in the story try to ambush them back - because if he pulls it off, HE is the big bad toughie of the neighborhood. Roll with your PC's in-story reputation !
I checked the math, and the sheet, and cross referenced it with the phb, and watched countless videos on stealth, surprise, sneak attack, crits, assassinate etc etc.

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Question, does he get involved a lot in the non-combat stuff too??

TBH, this guy sounds alot like me. He's created a murder machine that annihilates in combat. But he's also into rp. Considering he's a rogue, he quite likely is quite well equipped for the exploration pillar, and it's fairly likely he carved out some sort of social niche as well(deception being the way to go on assassin, due to the disguise stuff). This type of player is probably just somebody who just legitimately loves D&D, and throws himself into every aspect of it. The main drawback to this type of player is spotlight hogging(ie killing everything before other players get the chance, seeming to be better at all aspects of the game than the rest of the group, etc).

Some ways to deal with it are big bads that don't show up immediately(have a mook turn into an undead or get possessed by a demon or something when killed), have 2 big bads, have a big bad with a bodyguard, have a big bad that can survive the burst and recover, etc. Straight up denying him his abilities or weakening them will justifiably frustrate him. The trick is to let him do his thing(instantly splatter 1 enemy at the start of the fight) most of the time, but not making that instantly win the entire fight.
 

Tell me what is askew

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How are they surprising enemies every fight? What is the thought process that allows this? As I stated in my post it should happen maybe once a dungeon floor. In a standard party they might only ever get surprise a couple times a campaign. The boss should be smart enough to have wards against that sort of thing.
 


Level 5, completed cragmaw hideout, cragmaw castle, old owl well, rebrand ruffians, currently doing thundertree, then they'll do wave echo cave. It's worth mentioning that they used to have a different DM who started them at level 1 on CoS so took them through the death house and gave out random amounts of XP which is why they levelled up so quickly, then the DM got bored of CoS and moved them over to LMoP for one session, then got bored and quit, that's when I took over. So before the cragmaw hideout they were already level 3 or 4.

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I have been the whole campaign, I'm playing lmop and they should be fighting goblins with like 10hp or something stupid which is why I've been either buffing their health and damage or just replacing them with creatures with adequate cr
This might be the other way to handle the issue: Lots of waves of Goblins, with the boss coming in partway through. It doesn't matter if the assassin is dealing 50 damage as a first strike if what they are stabbing only has 10hp. :-)
 

Level 5, completed cragmaw hideout, cragmaw castle, old owl well, rebrand ruffians, currently doing thundertree, then they'll do wave echo cave. It's worth mentioning that they used to have a different DM who started them at level 1 on CoS so took them through the death house and gave out random amounts of XP which is why they levelled up so quickly, then the DM got bored of CoS and moved them over to LMoP for one session, then got bored and quit, that's when I took over. So before the cragmaw hideout they were already level 3 or 4.

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Just a quick one - can you list the monsters in the last major fight they breezed, and the number and level of the party at that time? Might be worth checking if it's simply about a minor encounter tweak....
 

But why?

It is good design.

Anyone caught out in the open, alone, unprepared should fall in Alpha strike from a mob of 5/6 trained killers.

That is why bosses have tons of mooks to be cannon fodder so the boss can take action agains the party when HE/SHE wants it.

Unless the boss has the ability to bounce the attacks on his goons, it doesn't really matter how many goons he has, he's still getting pasted round 2 tops. And sometimes you want a monster to be impressive solo, like Strahd. Except Strahd will be vaporized by any competently built party the second he shows his face due to his wuss HP, poor defenses and action economy. Yeah, you can do hit and runs (if lucky), but that's going to just piss your party off the second or third time and frankly isnt a fun table experience for either side.

Adding MMO style pointless trash mobs you have to chew through shouldnt be required. And here I thought 4E was supposed to be the video game edition? 5E relies extensively on the time wasting grind with its stupid 6-8 encounters per day.
 
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