What are the circumstances surrounding the money Lily Dale gives to the young man from Atlanta?

Will gives Lily Dale $5,000 for Christmas every year. He has done for the fifteen years prior to the action of THE YOUNG MAN FROM ATLANTA. On the one hand it is money that Pete earned, so he feels protective of it. On the other hand he gave it to Lily Dale to do with as she pleases, so it technically no longer belongs to him.