This is an interesting idea. I really appreciate riot's design team posting some early discussion like this. You guys do the work I want to do for a living and getting a good chance to armchair analyze actual live game tuning does a lot for me and is quite fun. I am just going to share some of my thoughts here and if they add to the discussion, great.
I think my first thought is that if we are going forward with the nightfall passive is to make sure the visual indicator is clear and visible. This strikes me as especially important in this case (clarity is always important) because peeling off an assassin is often a team effort and we should make sure supports can notice and identify this passive to perhaps save their squishy with the clutch shield or heal.
So let's frame the problem. (sorry if I am repeating things already in the OP here, I just want the assumptions and context clearly stated so that any mistakes in my understanding of the context can be separated from my thoughts).
AD assassins are currently lacking strong core item choices.
The Current items that work very well with AD assassins right now are basically:
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Yoomuu's Ghostblade (probably the best item for the class right now, really the only item that is specifically great for them).
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Maw of Malmortius (I think this is kind of an awkward choice because some of the power of the item is in its magic resistance and interaction with additional MR which makes it better as a single damage item on a heavier class of champions trying to fight a very AP heavy team. Side note, the lifesteal out of combat on lifeline trigger strikes me as on odd mechanic if this item is for assassins since they often build lifesteal anyway.)
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<insert raw attack damage and lifesteal items such as Bloodthirster and Mercurial Scimitar based on the game here> (these items are nice to have one of but still overlap with adc itemization and have the notable problem that stacking a bunch of them together doesn't give any kind of multiplicative scaling and so the damage just falls off.)
I will mention death's dance here because I think it could be an interesting next place to look but is currently struggling to distance itself from the other lifesteal options above.
So the missing pieces from last season seem to be:
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Brutalizer was removed and was probably the best early game power spike item on the class.
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ADC itemization (which assassin's had an overlap with) was shifted towards crit chance and attack speed as multiplying effects and the raw AD stat on the items was reduced.
Now we get to the big hole. AD assassin's previously built Last Whisper as a core item because of how well their kits interacted with armor penetration. This had a few problems:
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It gave the assassins a lot more target agnosticism than what was intended for the class since LW was a tank counter item to start with so they just killed everyone.
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LW was rather cheap and very gold efficient.
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Assassins buying LW made itemizing resistances against them significantly less valuable than it should be and often not a real option for some classes.
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LW as a core damage item on assassins to deal more damage to squishy targets is not intuitive and the math behind the armor mechanics was a small burden of knowledge on the assassin player (this isn't a huge deal but I think that it is important to note that without knowing the math; LW would not be a natural purchase given the description).
Brutalizer being replaced by Caufield's Warhammer and Serrated Dirk seems pretty intentional. The early power spike was probably as issue and the 1337 club was taking up some design space.
Overlapping with ADC itemization was already a problem and you guys fixed it in some key places.
So the problem seems to really be with the loss of last whisper as a main damage amplifier.
Let's see what Midknife (nightfall, midnight, mid lane assassins, get it?) does in this context.
First, this is another place to purchase more armor penetration. This is a key point for me because I think part of the problem is that flat armor penetration is basically the only multiplicative scaling stat for AD assassin damage. (Note: CDR is kit dependent but unlike for mages it usually does not increase burst potential or damage output in a given interaction since most burst is all in one combo of spells. Instead it increases uptime and attempt rate which are more macro level scaling concepts).
Second. The item's passive adds a damage multiplier that functions specifically within their burst windows.
Third. 75 AD is a lot of raw attack damage and does a decent job of setting the item apart from just buying something like an infinity edge for the AD and just shrugging about the crit that you don't perfectly utilize.
So far so good. This item addresses a few core problem with assassin items:
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It adds another strong first core item purchase next to ghostblade that shares a build path from Serrated Dirk
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It adds another damage multiplier that functions within their burst window
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It most likely won't seriously overlap with ADC items since the passive is not controllable and ADCs usually have to start a fight hitting a tank, often have to switch targets, don't really want flat armor pen, and don't want to spend this much gold on an item that does not fit in the AD/Attack Speed/Crit Chance interaction triangle.
Now we get to my feedback and suggestions.
My first thought on the item is that the reset on the passive seems to function more for giving the assassin a lot more power to help him clean up a tank at the end of a messy fight that he was successful in than it does to improve general use. Other posters have a good point too that the reset seems to reward an assassin that is already snowballing well enough with an additional fallback damage source for if a future fight goes a little less well than the first one. Fighting off an assassin is often a team activity and this extra mechanic that helps out the examples that need the least help seems unnecessary.
It strikes me that the core theme of my glance at this whole situation is that AD assassins benefit from flat armor penetration far more than anyone else does and it is a very rare stat. I think adding this item in to the game without really doing anything with their current option (ghostblade) just makes them build the best of the two items first and then build the other unless the game state demands they build a different item for a specific purpose like maw or mercurial or lifesteal. The fact that many assassins will simply build both items is a good thing if we plan for that ahead of time. This leads me nicely into my suggestion which is to take the example from the adc item rework, specifically the attack speed/crit chance items, and balance the options against each other directly.
So instead of simply dropping in another armor pen item for them to build lets create a set of them with nearly identical build paths, similar stats and costs, and goal based minor differences based on which active/passive the player wants first.
So the three items I suggest are:
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Yoomuu's Ghostblade.
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Death's Dance
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Midknife
Give all three items ~75 AD, 10% CDR and ~15-20 Armor Pen and have them build out of either Serrated Dirk or Caufield's Warhammer, perhaps both.
(may need to side on the lower end of armor pen per item if more of them exist in the game.)
The reason I think that a set of sister items is the best way to go here is that AD assassins are likely to simply build all of the items that give them the AD, CDR, Armor Pen combo that they want anyway and would just build them in order of stat value. Specifically designing for this with items that are differentiated by their role in the game solves the static build order issue and gives the assassin player meaningful item choices at the same time. Additionally with 2-3 of these items all in the game the assassin class has strong items to be buying for most of the game that all increase their value as assassins through adding additional tools built specifically around that role in a game and balanced specifically for them. It also gives better competitors for simply borrowing the AD+lifesteal items or buying ADC items just for the AD and makes the choice to build lifesteal or the mercurial active have a role specific opportunity cost.
So the roles I think they should represent are the three of the ways an assassination attempt fails:
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Play up the active on Yoomuu's Ghostblade as a gapcloser and chasing tool to help the assassin get to his target. First thought for how to do this is slow resistance.
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Death's Dance should be a stronger item at helping the assassin avoid getting counter-bursted. I have a few different ideas about how to create a burst prevention item for assassins such as an active that can't be activated if you have taken damage recently and causes your next auto attack to mark your target, reducing damage you take from that target or from everyone else. The former is really good in duels and the latter is probably too strong on reset champions. A lot of my other ideas at an anti burst item need it to lose its role as a caster based lifesteal item to fit in the paradigm and avoid abuse cases like olaf and other lifesteal tanks and overlap with sterak's gage.
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Midknife fits the role of an items that helps assassins get those last few points of damage in and solves cases where they just don't quite have enough burst. It already has the right passive to fit this role. I don't think that it should have %movement speed as part of the item in my system or in general as I think that it would be better served by putting something like that on ghostblade in my system or putting that power budget into armor pen in either case.
Closing note. For anyone that finished my post and read it carefully, I thank you for your time and I hope I have added to the discussion and that you will do the same. For the riot designers I would love any feedback not just on the content of this post but how I could format or better add to any future discussions I participate in. Apologies to all for the length.
-Neth.