| Answered By Rav Baruch Fried
Answer: Let's first discuss what the halacha would be for an adult. If someone tells a gadol that if he does a service for him, he will give him a certain thing, that deal would be binding because it is as if he hired him as a worker and agreed to give him that item [or its value] as payment. In this case, it could be argued that the counselor had essentially hired him to hit a home run and promised a Segway as payment, so he must keep his word.
The counter-argument to that would be that this is a case of asmachta. Asmachta means that if someone promises to give someone something for an action that no one really thinks he will do, that agreement is not binding because it was never meant as a real commitment. In this case, unless the kid is a real slugger, the counselor can rightfully argue that he never really thought he'd hit a home run and never really intended to commit to giving him a Segway, so his word is not binding.
Since the boy is a katan, however, there is another consideration. The Gemara in Sukkah [46b] says that one shouldn't tell a child that he will give him something and then renege on his word because doing so would be teaching the child to lie. It isn't clear what exactly the case of the Gemara is. If it is talking about an instance where the child is really owed the item, the adult obviously has to give it to him and the Gemara wouldn't need a new reason for it. Thus, it seems that the Gemara is talking about a case where there is no real obligation to give it to the child, and yet, the adult should keep his promise so that the child doesn't learn how to lie.
The case in question sounds like that kind of situation. This boy will remember that his counselor "owes him" a Segway and will never get over it if he doesn't receive one; therefore, if it is at all doable, he definitely should get him that Segway. | 
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