Oliver organized a penny war fundraiser, where everyone brings in change and the class with the most donations wins a prize. He made every class a donation bucket, created informational posters for the table where the donation buckets would be placed and gave a presentation to the entire school about the need in Jamaica and facts about the hurricane. He also helped count and tally the donations.

Oliver got the entire student body (most of whom are not in Scouting) of his school involved, as well as faculty and parents, in fundraising for disaster relief for Jamaica. This project helped highlight the situation in Jamaica, and the needs of its people, to youth in the United States, many of whom might not have been previously aware; or that don't have experience thinking on a more global scale due to their age and inexperience. Oliver's efforts to raise funds taught a valuable lesson to his peers at St. Roberts School. Additionally, he brought the presentation he gave to the school assembly to a den meeting and educated his fellow Bears on this issue.