First off, you're not condescending, and if you were it might be appropriate, as this is only the second campaign I've GMed, and the first hardly counts. You seem much more experienced with running AW as it is designed than I am.
Join me or die: When you and your gang have an utterly dominating position on a few NPCs or less not belonging to another PC, and try “convincing” them it’s in their best interest to join your gang, roll +hard: On a 10+, they join you at no cost and are fairly motivated, at least for now: choose none and take +1 to gang-related moves. On a 7-9, they join you for now, but with a catch: choose 1. On a miss, they join you for now, but you’ll really wish they didn’t.
- You have to put down the rebellious half first or they’ll be out of commission for a while after you’re done with them.
- They’re fucking thieves, alright, but not always in your favor. The GM gains 1 hold to take something from you when you need it most. Can’t be countered by the Fucking Thieves move.
- This crew isn’t as useful as you first thought and is going to take some breaking in. Lose 1 gang benefit or gain 1 gang vulnerability, the MC will tell you which, until the next time you use this move or the problem is resolved, as appropriate.
Sorry, this move was definitely not meant to work on PCs, I just forgot to specify that. When it comes to NPCs that you know would NEVER join the gang, well, there are already mechanics for that: the advanced Going Aggro and Seduce or Manipulate moves. This move is supposed to read like a 12+ Go Aggro. One of the things I like about this game is that sometimes you can make things happen that shouldn't be able to happen, cause you're a badass. There are no truly in-any-way untouchable NPCs, if going by AW principles and rules. That said, I understand the problem of a major "antagonist" suddenly being a happy member of your gang for only a 10+ or even 7-9. There a few possible solutions I can see. Let me know which you think is best or if you have any alternative solutions.
1. Specify that the move can be used only at the MC's discretion, which goes against the "say yes or roll dice" principle, so this option isn't my favorite.
2. Specify that the move can be used only on nameless NPCs (because nameless NPCs are never that strong-willed). This also isn't ideal to me, because I like the idea of named NPCs joining your gang. It establishes some on-scene prior history with gang members, which I think could be neat. This is negotiable though.
3. Rework the move so that even at best, there is potential for sabotage by vindictive and tactical NPCs of importance. This is definitely doable.
4. Specify that no matter the result, they only join your gang "for now" (whatever the reason), and might choose to leave almost immediately. This is the one I choose for now, but it's not my preferred choice either.
I reworded the move requirements so you should no longer be able to "lose ten battles and win the war," take other character's gang members, or increase gang size without putting in a lot of time, as well as not using your gang as a weapon for many sessions.
Also, I originally said: "You could just say they gain gang members when the time seems right narrative-wise, or you can use this if it seems useful or interesting to you." What I realize now, is that this move is meant to be used in addition to the "They need to get more guys for their gang, so they do and the MC attaches strings" attitude. This move is meant to replicate something I think fits in this type of game, as well as fill out gang members: Overwhelming someone and then demanding they work for you. (This is also why the barter moves aren't scratching the right itch, though I failed to mention this motivation in my first post). That wouldn't be the only way to gain gang members, and everything else could be handled as you described!
Hopefully I've de-macroed the move enough to be acceptable. By the way, since this move is definitely supposed to be more Go Aggro than Seduce or Manipulate, one could argue that the Going Aggro basic move could be good enough for what I'm trying to do here, and they wouldn't be wrong. I just personally wanted something surrounding this idea that was a little more specialized.