Well what he really did was pass the burden over to Ralphie. He did that to remove any self guilt that he would have incurred had he directly ordered the hit on Jackie Jr. I don't know that he was hoping that the kid would be spared. From what I remember from that episode, he basically told Ralphie, without telling Ralphie, that because he was a captain then he would have to act like one and be responsible for what took place. A part of me feels that Tony was telling Ralphie that if he didn't make the right decision himself, then Tony would hold him personally responsible for what took place. He really did not give Ralphie a choice although he made it appear as if he did.

In other words he justified it within himself, cleared his own conscience, by passing this burden on to Ralphie. Now if something now happened to Jackie, he wouldn't have to feel guilty about it because he himself was no longer responsible.

Tony had a smooth way of ridding himself from making those kinds of decisions and putting the burden and responsibility on others. It all had to do with his inner psychological battle. Let's not forget that the whole premise of this show was to show us a mob boss who had somewhat of a subconscience and needed to deal with his inner battles through therapy.