Name: David Cain
Skills: Assassin skilled in many forms of armed and unarmed combat, peak physical condition, Master spy and Master Martial Artists.
Why: Being a top assassin it'd be no surprise as to why Black Mask would find and hire him to kill Batman, not only did he train a young Bruce Wayne, framed him for murder and can give him a run for his money let me say if he's in this game out to kill me as Batman gamers need to be prepared because he is no cake walk as a boss. Also he has a bad relationship with the other two assassins Deadshot and Deathstroke.
Name: Lady Shiva aka Sandra Wu-San
Skills: Not only is she one of the most skilled martial artists in the whole DC Universe she shares her title with other great fighters such as Batman, Black Canary, and Richard Dragon among few others. She's mastered fighting styles such as Leopard and Dragon Style Kung Fu, Stick Fighting, Judo, Capoeira, Karate, Kokusho and Savate. Mix that with her Tatical Skills and total control of her emotions and blood flow and you've got another serious contender.
Why: "Her hobby is hunting down the best fighters in the world and beating them to death with her bare hands" said by Barbara Gordon you'd think that would be enough but there is always more, Shiva sells her services of assassination for the money and the challenge it brought her so why not give her the challenge of Batman as well as the other assassins after him?
Plus let's not forget who David Cain and Sandra are the parent's of.... Possible forshadowing to Cassandra Cain aka Batgirl in a future Arkham Title!?
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Name: Jade Nguyen aka Cheshire
Skills: Being a skilled and deadly assassin she's got the skills of an acrobat and skilled martial artist, also being a poison specialist can help with her caliber of killing her targets.
Why: Black Mask is going to need diversity with his assassins each to be different from the last offering all kinds of skills Batman will have to think twice about as well as something he isn't ready for, and being poisoned by her blades or nails even isn't something Batman would be ready for.
Name: Arthur King aka Merlyn
Skills: Being one of the best archers in the world is not an easy thing to have on your resume as a villain and of course being an archer goes back to the diversity I mentioned earlier and whats more diverse than bows and arrows in a city of guns and bullets. He's a Green Arrow villain MrDarkPhoenix how can he fit in the game? Being an assassin Black Mask can hire one but here's a more important reason:
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