Fairly stupid that the "challenges" are just a matter of playing enough times until the right hand appears. Not much skill involved there, just persistence.
At least on "normal" it quickly reached a point where I was just setting up my guys and hitting "fight" without even bothering to look at the defenders.
Even on "hard", if you start with 2 hatchet men and 1 money woman and the computer starts with any combination not including 2 hatchet men and 1 money woman, you can always win. The other staffers are just not as strong.