Contract on the kid? Spoilers!
When Nitti was talking to Rooney Sr. about hiring the hitman Rooney made it clear he did not want the boy killed. Nitty then says something about boys growing up to be men with grudges, or something like that. Then Nitti is talking on the phone to Maguire and Maguire asks if the boy is to be killed as well. All we see is Maguire making a box out of the number one (he had written the boys age '12' during the conversation) and inside the box he draws an unhappy face. So, did the contract include the boy and if so did Rooney Sr change his mind? Did Nitti make a unilateral decision? Was the unhappy face drawn because he was NOT to be killed and Maguire was such a sicko that the unhappy face was because he wasn't going to be able to kill a kid?
I just saw this for the second time since it was released and I was reminded that I never did understand what happened there.