By default you cannot assign winnings to a member that has not paid into a league on LeagueSafe.
Here are the steps to allocate funds to owners who have paid offline (for a commissioner):
1. Log in to your league and go to the Manage Owners tab.
2. Click edit next to the owner in question.
3. Change their entry fee to $0.00.
4. From the Notify Owners tab, send them a league invitation. They will need to join the league AND have an account with LeagueSafe in order for you to send them any league funds.
5. Once they join the league you should be able to allocate payouts to them.