The perfect all Rogue party?

I would give the assassin the crossbow expert feat and maybe splash a fight level on one of the front liners. Try and get the Mastermind the green flame blade cantrip.
 

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party of 5 wood elf assassins.

Alpha strike or bust.

Wood elf gives more oportunity to hide, +5 ft extra movement(when surprise fails it's extra 15ft with double dash for running away), longbow for extra damage and larger range of alpha strike.

Elven accuracy and alert must have feats for all.
 

Oof, fiendish! In dungeon and urban environments, they might not get the full benefit, but in wilderness encounters, they'd decimate many threats before they could even get in range.

party of 5 wood elf assassins.

Alpha strike or bust.

Wood elf gives more oportunity to hide, +5 ft extra movement(when surprise fails it's extra 15ft with double dash for running away), longbow for extra damage and larger range of alpha strike.

Elven accuracy and alert must have feats for all.
 

One of them should have the sage background, party needs a loremaster

Inquisitive Sage. Human variant, with Healer and Medicine as bonus Feat/Skill. Expertise in Medicine and Investigation.

Alternately Magic Initiate feat, with Spare the Dying, Guidance, and Healing Word, and high Wisdom.
 

Honestly I think what you are describing is pretty much a DND version of a Special Forces strike team, and it would be very effective. Rogues are one of the most versatile classes, expertise is just crazy good, and I'm sure this party would work. Each of them could get out of combat if they wanted, Dex based means they are good at range as well as Close Combat. With stealth they will often get to choose when/where the fights occur if the players are even a bit cautious. And for once, the sneaky scouting rogue wouldn't likely be the only guy scouting ahead with his butt on the line.

I'd give at least one of them a decent WIS and the Observant Feat. That is a great feat, almost broken. I'd also give at least one, more if you can spare the feats, the Healer Feat. Not a ton of healing, but a decent amount and can do it once per short rest for each party member. Sometimes it comes down to a player just needing to take one more hit, but even then can be stabilized with 1hp and back in action shortly after things get under control. Since every party member can disengage as a bonus action those in trouble have a far better than average chance of getting out of it. Also, Dash as a bonus action you're group will have a huge tactical advantage if they have room to run around.

This idea would be effective. Biggest problem you'll have it PC's that think roleplaying is the same thing as whatever is on your stat sheet. If everyone is a rogue, there will be a good deal of overlap in abilities, and some players will feel like they aren't special. Essentially, ask your players what they do to make their guy a tavern brawler. If they answer "I'd need to get the Tavern Brawler feat" they probably wouldn't like this type of party. If they answer, "I tell the DM I'm going to a tavern, then I'm going to punch someone in the face", then they would probably do well in this type of party.
 

I'd give at least one of them a decent WIS and the Observant Feat. That is a great feat, almost broken. I'd also give at least one, more if you can spare the feats, the Healer Feat. Not a ton of healing, but a decent amount and can do it once per short rest for each party member. Sometimes it comes down to a player just needing to take one more hit, but even then can be stabilized with 1hp and back in action shortly after things get under control.


The Thief has the Healer feat. I guess you didn't see it.


Good call on Observant. I agree it is a good feat. I only listed 2 or 3 feats for all of them so there would almost certainly be room for one or more of them to grab it.


I also think one or two of them should pick up Ritual Caster too.
 

I'm going to suggest something a little outside the box, may not work for your vision but I think it might be fun from both a game play and RP point of view.

What you seem to be missing is muscle. A front line tank. Somebody with a good athletics score. Yes, the swashbuckler is front line but they're the hit and run front line. You need a guy that can block the way for a round or two.

So there are a couple of ways of doing this. The goal is someone with a lot of HP so I'd add the Tough feat.

Go against the grain and have a strength based rogue, maybe a mountain dwarf for medium armor and the strength and con bonus. If that doesn't appeal, Moderately Armored feat would give someone medium armor and a shield. A dragonborn thug could fill this role nicely with their bonus to strength and charisma.

In my experience stealth is great, but most monsters have a pretty low passive perception so limiting yourself to 14 dex isn't the end of the world and there's magic that can help if needed.
 

party of 5 wood elf assassins.

Alpha strike or bust.

Wood elf gives more oportunity to hide, +5 ft extra movement(when surprise fails it's extra 15ft with double dash for running away), longbow for extra damage and larger range of alpha strike.

Elven accuracy and alert must have feats for all.

Also, they could take the Wood Elf Magic feat and all be able to cast , Guidance, Longstrider and Pass Without Trace. PWT is insane for sneaking around, and can affect the whole group. Basically they could be in it almost all the time, certainly when it counted. And 45ft move instead of 35, with Cunning Action? Oh yea, your boys could hit and run with the best of them even from a very low level.
 
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I'm going to suggest something a little outside the box, may not work for your vision but I think it might be fun from both a game play and RP point of view.

What you seem to be missing is muscle. A front line tank. Somebody with a good athletics score. Yes, the swashbuckler is front line but they're the hit and run front line. You need a guy that can block the way for a round or two.

So there are a couple of ways of doing this. The goal is someone with a lot of HP so I'd add the Tough feat.

Go against the grain and have a strength based rogue, maybe a mountain dwarf for medium armor and the strength and con bonus. If that doesn't appeal, Moderately Armored feat would give someone medium armor and a shield. A dragonborn thug could fill this role nicely with their bonus to strength and charisma.

In my experience stealth is great, but most monsters have a pretty low passive perception so limiting yourself to 14 dex isn't the end of the world and there's magic that can help if needed.

I thought about having one of them(Assassin maybe?) be a Bugbear for those reasons. He wouldn't need to have 18-20 Str but a 14 or maybe even 16 should be easy to come by without hurting Dex too much. I do like the Moderately Armored feat for Rogues.
 

party of 5 wood elf assassins.

Alpha strike or bust.

Wood elf gives more oportunity to hide, +5 ft extra movement(when surprise fails it's extra 15ft with double dash for running away), longbow for extra damage and larger range of alpha strike.

Elven accuracy and alert must have feats for all.


I like this. It would be one hell of a first round indeed. Imagine how the first round would go for 5 level 17 Thieves with all of them getting 2 turns lol
 

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