Rogues actually got two new subclasses in Sword Coast Adventurer's Guide, both of which saw reprints in Xanathar's Guide to Everything. So the order here's going to be a little odd. Let's get straight to it!
Mastermind:
The Mastermind Rogue has a pretty cool fantasy to it - you're the genius crime boss, a student of human(oid) nature who can act as something of a leader within your group, rather than simply being the guy they send to check for traps or set them off before the rest of them get there. I really like the idea of playing a powerful manipulator (they seem like they'd be at home in House Dimir, though to be fair basically every Rogue would fit there, except maybe the Scout and Swashbuckler.)
At level 3, you get Master of Intrigue. You gain proficiency in the disguise kit, forgery kit, a gaming set of your choice, and you learn two additional languages of your choice. Additionally, you can mimic the speech patterns and accents of a creature you hear speak for at least 1 minute, enabling you to pass as a native speaker of a particular land if you know the local language. That's a whole lot of proficiencies, and already sets up some fun deceptions and manipulations.
Also at 3 you get Master of Tactics. You can use the Help action as a bonus action, and if you use it to aid an ally in hitting a creature, the target can be within 30 feet of you, rather than within 5 feet as usual. So, basically, once a turn you can give someone advantage and also stay at range when doing it. Nice.
At level 9, you get Insightful Manipulator. If you spend 1 minute observing or interacting with a creature outside of combat, you can learn if the creature is your equal, superior, or inferior in terms of Intelligence, Wisdom, Charisma, or class levels (if any.) At the DM's discretion, you might also realize you know a piece of the creature's history or one of its personality traits. This is very much a subclass that is built for social encounters and intrigue, great in an RP-heavy campaign.
At 13, you get Misdirection. If you are targeted with an attack while a creature within 5 feet of you is granting you cover against the attack, you can use your reaction to have the attack target them instead of you. This makes me feel the need to re-read rules about creatures providing cover for one another - you'll need to position yourself very carefully to take advantage of this.
Finally, at 17, you get Soul of Deceit. Your thoughts cannot be read by telepathy or other means unless you allow it. Also, you can present false thoughts by succeeding on a Charisma (Deception) check contested by the mind reader's Wisdom (Insight) check. Additionally, whatever you say, no magic that can determine if you're telling the truth indicates that if you so choose, and you can't be compelled to tell the truth by magic. This is a nice cover in a high-level intrigue-filled game - you can lie to an angel and they might believe you.
In terms of combat, the Mastermind has very little in the way of big features, which is very unusual for a subclass. But for RP purposes, this subclass is amazing for social encounters.
The Swashbuckler:
Rogues tend to have a reputation for sneakiness and shadows, but if you want to go full-on Errol Flynn, this is the subclass for you. You might still be a rapscallion ne'er-do-well, but you'll be very dashing and probably super attractive.
At 3rd level you get Fancy Footwork. During your turn, if you make a melee attack against a creature, they can't make opportunity attacks against you for the rest of this turn. This is a great way to get in, hit, and then get out.
You also get, at 3rd level, Rakish Audacity. You gain a bonus to your initiative rolls equal to your Charisma modifier. Additionally, you get an additional way to gain sneak attack on a foe. If you are within 5 feet of the creature and no other creatures are within 5 feet of you, and you don't have disadvantage on the attack, you will get sneak attack. Yes, this is the great "out in the open" Rogue. Who needs all that sneaking around and shooting arrows from the shadows. What ho!
At level 9, you get Panache. As an action, you can make a Charisma (Persuasion) check contested by a creature's Wisdom (Insight) checks if you share a language. If you succeed on the check and the creature is hostile to you, it has disadvantage on attack rolls against creatures other than you and also can't make opportunity attacks against creatures other than you, and this effect lasts for 1 minute or until one of your companions attacks the creature or affects it with a spell, or if you move more than 60 feet away from them. If you succeed on the check and the creature isn't hostile to you, it is charmed by you for 1 minute, or until you or any of your companions do anything harmful to it.
I love this, as you can just imagine that a Swashbuckler is just letting loose with quips and witty taunts the entire fight, and it has a tangible benefit in combat. Also, being able to charm people for free an unlimited number of times per day is pretty damn great.
At 13, you get Elegant Maneuver. You can use a bonus action to gain advantage on the next Dexterity (Acrobatics) or Strength (Athletics) check you make that turn. These are both pretty common rolls, and obviously are there for you to succeed on the "use a dagger to descend a big banner or the sail of a ship safely" thing.
Finally, at level 17, you get Master Duelist. If you miss with an attack roll, you can roll it again with advantage. You can do this once per short or long rest. Not only does this let you let you turn misses into hits, but the advantage also gives you sneak attack, so this can be a really great turnaround.
I think the Swashbuckler really excels at taking the fantasy of the subclass and making it work mechanically. It seems fun as hell both to play and roleplay.
The Inquisitive:
Remember that scene in the Guy Richie Sherlock Holmes (the first one with Robert Downey Jr.)? Remember that scene where he's in the boxing match and time slows down and you can see him analyzing the big hulking brute he's fighting and, in a split second, figuring out just where to hit him to take him down? That's this class. You can be Sherlock Holmes. And that is freaking awesome.
At level 3, you get Ear for Deceit. If you make a Wisdom (Insight) check to see if a creature is lying, you can treat any roll on the d20 of 7 or lower as an 8.
You also get Eye for Detail. You can use a bonus action to make a Wisdom (Perception) check to spot a hidden creature or object or make an Intelligence (Investigation) check to uncover or decipher clues. I think this is niche - how often do you need to make such checks in the heat of battle? But it's going to be very good when you need it.
Finally at 3, you get Insightful Fighting. You can make a Wisdom (Insight) check against a creature you can see that isn't incapacitated, contested with its Charisma (Deception) check. If you succeed, you can use Sneak Attack against it as long as you don't have disadvantage on the attack roll, and this benefit lasts for 1 minute or until you successfully use this on a different target. Giving Rogues alternate means to get Sneak Attack is great, and I think this basically is the mechanical representation of that aforementioned scene from the Guy Ritchie movie.
At level 9, you get Steady Eye. You have advantage on any Wisdom (Perception) or Intelligence (Investigation) checks if you move no more than half your speed on your turn. Like with the Thief's advantage on stealth, this seems like it'll be always on in most situations (namely outside of combat,) but could also prove useful if you need to spot something in combat (and can use Eye for Detail.)
At level 13, you get Unerring Eye. As an action, you can sense the presence of illusions, shapechangers not in their original form, and other magic that can deceive the senses within 30 feet of you as long as you aren't blinded or deafened. You get a sense that there's something trying to trick you, but you don't learn specifically what is being hidden. You can do this a number of times equal to your Wisdom modifier (minimum of once) per long rest. This is a great way to ping out for anything weird, and could be a great way to get to the bottom of a mystery.
Finally, at level 17, you get Eye for Weakness. While you have Insightful Fighting on a creature, your sneak attack against them increases by 3d6 damage. You're probably going to be using this all the time with this subclass, so this is a pretty nice bonus to damage, if not mind-blowing.
Like the Swashbuckler, I think the Inquisitive really fits the fantasy and the mechanics together very well, and I'd be excited to play one.
The Scout:
Finally out of Xanathar's we have the Scout. The Scout pushes you into more of a military or outdoorsman role - less of a spy, thief, or assassin and more of a soldier or commando.
At level 3 you get Skirmisher. You can move up to half your speed as a reaction when an enemy ends its turn within 5 feet of you, and this does not provoke opportunity attacks. This is a great way to not get hit more than once, so I'm all for it.
You also get Survivalist. You gain proficiency in Nature and Survival if you don't already have those skills, and you effectively get expertise in them, doubling your proficiency bonus for them. As if Rogues didn't get enough skills! You'll be a capable forester with this.
At level 9, you get Superior Mobility. Your walking speed increases by 10 feet, and if you have a climbing or swimming speed, they also increase by these amounts. More movement is great, even if this is a bit of a simple feature.
At 13, you get Ambush Master. You get advantage on initiative rolls, and all attack rolls against the first creature you hit in the first round of combat have advantage until the start of your next turn. So, you can really ruin a foe's day if you hit them that first turn - great for an opening salvo against a boss, or just taking out a key foe in a group asap.
Finally, at 17, you get Sudden Strike. If you take the attack action on your turn, you can make one more attack as a bonus action, and you can benefit from a second Sneak Attack for that attack as well as long as it's a different target than the first attack (if you miss with the first attack, you can still get a Sneak Attack on it if you hit with the second attack.) This is freaking hugely powerful, effectively doubling your damage each turn.
While the Scout is much less to my tastes, conceptually, it's definitely powerful mechanically, and admittedly is a very different take on the Rogue, which is pretty cool.
Next post, we'll handle the spooky weirdness of both the Soulknife and the Phantom.
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