Swashbuckler Rogue

 The only reprint that sticks with its original name, the Swashbuckler is actually one of the most iconic rogue archetypes. In the One D&D playtest for 5.5, they originally planned to have the Swashbuckler as the PHB's fourth Rogue subclass, and as much as I like the Soulknife, I do think that this is far more of an obvious, core Rogue fantasy that really deserves to be one of the basic options.

This is the Rogue who doesn't hide in the shadows, but walks into the false-king's banquet hall pointedly holding a poached deer. It's the most classically-heroic Rogue, potentially, though typically in the role of a scrappy underdog. Through wit, charm, cunning, and rakish audacity (so to speak,) they make fools of their foes.

Now, because this is appearing in the WoW book, let's give a little history of the Outlaw spec, which began its life under a different name.

In WoW, all three Rogue specs dual-wield melee weapons - there's no ranged Rogue, and they're the only pure-melee class that cannot perform the tank role (Hunters and Shamans each have a melee spec, but they're more often fighting at range). Furthermore, the other two specs, Subtlety and Assassination, fight only with daggers, while these Rogues fight with a larger array of weapons - swords, maces, axes and fist weapons.

When WoW came out, the spec was called simply "Combat," and while it was, actually, often the best spec (back when the balance of the game was far worse and certain specs were truly just better than others,) its flavor was... you fight with larger weapons.

However, come the Legion expansion in 2016, Combat was renamed to Outlaw, embracing a far more specific and flavorful identity, and changing up a lot of its abilities, including incorporating a pistol that the Rogue would draw and fire to use certain abilities (not equipped as a piece of gear, the pistol was more of just a visual for the abilities). Outlaw can be interpreted as having more of a pirate/swashbuckler vibe, though there's also a bit of a Wild West gunslinger (with a bit of a gambling theme - true to both archetypes).

A spec I avoided like the plague because it was so boring prior to this, Outlaw is actually very fun now, and while I still love Subtlety best, I do have a secondary Rogue character in WoW who goes Outlaw.

Now: the D&D subclass, however, does not appear to be in anyway pulling on the WoW spec for its mechanics. This looks to be almost purely a revision of the existing subclass that was last seen in Xanathar's.

Let's get into it!

Level 3:

Fancy Footwork:

When you make a melee attack against a creature, it can't make opportunity attacks against you for the rest of your turn, whether you hit or miss.

    This is, I think, unchanged, but also strongly enables you to get up into melee as a Rogue. With your bonus action no longer needed to disengage (unless you get up in front of multiple foes) you free it up for either a dash (to get back away from that enemy you just attacked) or to make an off-hand attack (though thanks to weapon mastery, we're probably not worried as much about that, though we might if we get the Dual Wielder feat), or have some other thing to do. It makes us very mobile, which is great.

Rakish Audacity:

You get a bonus to your Initiative rolls equal to your Charisma modifier. You can also use Sneak Attack without advantage if you're within 5 feet of a target and no other creatures are within 5 feet of you and you don't have disadvantage.

    Again, I think this is unchanged.

    Rogues can afford to be fairly "SAD" (single ability score dependent) and so you can actually manage to have a decent Charisma. It's already a Dexterity-focused class, so you'll have a pretty good initiative bonus anyway, and if you get something like Alert, even better.

    Now, the second part here is the real boon: We can basically always get sneak attack. While it might be hard to do if we want to strike a foe surrounded by its allies, I think we can usually find a space to stand where we'll only have one foe within melee range. If that space is within 5 feet of an ally, then we're probably getting Sneak Attack anyway because they're also likely within 5 feet of our target.

    The only bad scenario here is if we can only get into melee with a foe while an ally is just out of reach of the foe. But that's pretty unlikely, and so what I think this means is that we can be very confident we'll get sneak attack - if we're going into melee.

    Again, I think this is identical to the old version, but this is another feature that I think makes this subclass a popular choice for 3-level Rogue dips.

Level 9:

Panache:

You gain two new Cunning Strike options.

    Just as a note: I love the idea of Cunning Strikes. But I do think that their deep flaw is just that Rogues are already struggling to keep up in terms of damage, and so sacrificing damage for utility feels a bit unfair when you have, say, Battle Master Fighters getting utility on top of damage with their maneuvers. If Sneak Attack did significantly more damage (some have suggested even letting it scale every level, so you have a d6 for each Rogue level) this might work out better. But that's not this subclass' fault, nor is the fact that their second subclass feature doesn't come online until level 9.

Goad (1d6): The target makes a Wisdom saving throw. On a failure, they have disadvantage on attacks against creatures other than you until the end of its next turn.

    So, this is a taunt, though with a save to avoid it, unlike what, say, Ancestral/Spiritual Guardians or Armorers get. The real question, though, is... do you want to taunt a foe? Rogues do have one solid defensive reaction, but it only halves incoming damage. Here, though, I think this becomes far better if we are fighting from range, where they won't even be likely to be able to target us in the first place.

Awe (3d6): Creatures of your choice within 30 feet of you make a Wisdom save or become Charmed until the end of your next turn.

    An AoE charm can be very good, defensively. Hard to use outside of combat, of course, given that you have to land a sneak attack. A real flavor win, though, as this feels like a great thing to use when you're alone in a room full of enemies and have to beat a hasty retreat.

Level 13:

You get even more Cunning Strike options:

Invigorate (2d6): One creature within 30 feet adds 1d6 to their attack rolls and saving throws until the end of its next turn.

    This is kind of fascinating. I believe (again, the wording here isn't precisely what's printed in the video I'm using as a source) you could target yourself with this. But if you have an ally concentrating on a really important spell, or you have some friend who has some really great buff to their attacks, this could wind up being very nice to hand out. We lose 7 damage, but that might be made up for by this bonus.

Parrying Stance (2d6): You add 1d6 to your AC until the start of your next turn.

    Especially given the melee focus on this subclass, getting a way to boost AC will be nice. While by level 13 we should hopefully have capped our Dex (even with three General Feats, if we start with 17 we will be there) and thus we should have comparable AC to someone in half-plate, a little extra is certainly nothing to say no to. But this really is a weighed choice between better survival and a chunk of our damage.

Level 17:

Master Duelist:

Immediately after using Sneak Attack, make another attack against the same target, provided you're within 5 feet of it and no other creatures are within 5 feet of you.

    This looks pretty good, but we have to temper our expectations a bit: that second attack can't trigger Sneak Attack by definition. Also, if we miss on our attack, we don't get this. I do think that this really, really encourages a Swashbuckler to dual-wield, and even take the dual-wielder feat, which is already pretty helpful for any Rogue.

Overall Thoughts:

    I think this subclass is fine, and good, even, but we do have to grade on a curve for Rogues. If we pumped the Rogue up a little bit (and moved the second subclass feature to, like, level 6) it'd be amazing.

    I think you can potentially get the same kind of Errol Flynn-like swashbuckling flavor with, say, a Valor Bard and might actually feel like you're pulling the whole archetype off even better that way. But if you do want to play a Rogue, I think this is going to be a good choice that does enable a lot of what you're looking for.