Aomine, Momoi, Imayoshi, Wakamatsu, Sakurai as gang leaders (preferably in one gang), headcanons for their position, assigned tasks, rides, etc. Thank you!!

Since they are all in the same gang I’ll substitute the word
“leader” for “members” since there’s really only one leader usually. If I
misunderstood please let me know. Also, I’ve been noticing a lot of what I’m
coming up with feels more “mafia” than bad boys but really isn’t the mafia
just a more sophisticated kind of gang? Oh well, we’ll just keep rolling.

Imayoshi – Leader

• Decides who, what, when, where and why things either happen
  or don’t.
• His ride is a black BMW with black out tint and bullet proof
  glass, most often times driven by either Wakamatsu or Sakurai.
• Weapon of choice: switchblade.

Wakamatsu – Right hand man

• Steps in when Imayoshi is preoccupied, next to ascend to
  leadership if something happens to him.
• Somewhat of a body guard, usually found with Imayoshi at all
  times.
• If he’s not playing driver to Imayoshi, he can be found in his
  classic red Camaro.
• Weapon of choice: Beretta M9

Aomine – Enforcer

• Not involved in the day to day “work” of the gang because he’s
  too damn lazy.
• Sent for “negotiations” with rival gang members or infiltrators
  to Too’s territory.
• Shoots around town on his black and red Yamaha 750cc sport
  bike.
• Weapon of choice: His fists

Sakurai – Sniper “The Regretful Reaper”

• Despite his timid nature, Sakurai is one of the most feared
  members because of his top shot.
• Roll is to annihilate targets either through a hired job or
  retaliation.
• Doesn’t drive the same vehicle twice to avoid possible
  detection. Usually steals one, does the job and leaves a note with “I’m sorry”
  written on it.
• Weapon of choice: sniper rifle

Momoi – The Source/Intel Gathering

• Handles all the nitty gritty details of payroll (yes, they
  get paid because they don’t have time to have jobs), target acquisition,
  accepting payment for jobs and gathering intel on friends and enemies alike.
• Keeps the gang in check (even Imayoshi from time to time) to
  ensure things continue running smoothly.
• Has a cute little scooter she uses to shoot around town.
• Weapon of choice: Blackmail