Back when rogues were thieves, they were reliable too. The party could count on them to climb walls, hide in shadows, hear things, etc. Backstabbing almost seemed to be an afterthought. But as the class progressed, things changed. The thief become an agent of luck and disorder. The thief was meant to thrive in a chaotic environment, which they often helped make ever more unpredictable. This transformation seemed to be completed by 3rd Edition D&D, when it became the "rogue" and was now focused less on some special set of technical skills and more on the ability to slip from danger and create danger at the blink of an eye.
Personally, I prefer the scoundrel rogue to the simple thief. Not only does the idea of a rogue easy subsume the thief concept, if desired, but it also helps avoid the horrible abomination that is Bad Trap Syndrome, since the thief has ever been the "bad trap disarmer."
So on that note, here we go.
D&D Classes Without Math: The Rogue
Rogues are about big risk and bigger reward. It is hard to think of a better character for a fantasy game based around rolling dice. With that in mind, here are my core rogue features in no particular order:
1. Lady Luck's Re-roll
All rogues should have some ability to reroll a die during the day. This does a lot of ground work to establishing the kind of character a rogue is, but it also helps the player. You are much more likely to try something risky if you know you've got a lucky break in your back pocket. As a matter of taste, I would say that the player MUST take the second roll, even if it is worse. Hey, lady luck works both ways....
2. Surprisingly Dangerous
Backstab is great is theory, tough to do in practice. I'd give rogues a loosened up version where so long as the enemy is unsuspecting, the rogue does a buttload more damage. I'd also play hardball and say that once you engage an enemy, you must completely lose them to get the bonus damage again. Simply ducking behind a tree or flanking with a buddy is not enough. Skirmishing rogues are good, swashbuckling rogues are good, but I despise the "bonus damage every round for barely any work" shtick that is seen in 3E, 4E, and 5E D&D. Lazy rogues are a no-go.
3. How'd He DO That?
|The quintessential rogue, getting a magic item to work.|
4. Cover Your Rear End
Rogues are not stupid. They may be foolish, but they know how likely it is they will die if they make a serious misstep. But that being said, someone has to try and parley with the dragon, and it's probably gonna be the rogue. So, best that they know how to cover their butt. For my tastes, this is simply an option to forgo some attack bonus for extra AC, a la the Expertise feat in 3.5 D&D. Or perhaps rogues could receive an AC bonus on turns when they use their action to run. Pretty much anything that helps them get the hell out of dodge in one piece is gonna hit the sweet spot.
5. Grab Bag
Unlike the other grab bags so far in this series, this one is a literal grab-bag type class feature. Rogues are a varied group, even more so than fighters, rangers, etc. Where a fighter's unique personality comes through in his or her choice of arms and armor, and a ranger's comes through in his or her choice of animal companion, a rogue's personality should come through by selecting one feature from a list of three or four. These features might include a special secret thief language a la Thieves' Cant in 5E, it could be a "get out of jail free card" type dodge where the rogue can reduce damage they take by half from one attack a day, it could be a second reroll for the day, but only usable on charisma checks, and so on. Part of the charm and flavor of rogues is never knowing what they are hiding. This is the mystery icing on the scoundrel cake.