Oliver Porter Killam Jr. had a restless curiosity and a willingness to take risks that shaped his life in unexpected ways. Raised in Boxford, Massachusetts, he was just 17 when he set off on a cross-country drive to see the United States for himself—a bold undertaking at a time when the highway system was still developing. That independent spirit stayed with him as he built a life filled with varied pursuits.

He eventually settled in Marblehead, Massachusetts, where he explored different careers. He ran a restaurant, founded a sign company, crafted furniture for schools and businesses, and purchased a large Pleasant Street property (now home to The Mariner Marblehead). But it was in the stock market that he found his true financial success, developing a keen knack for investment.

When Oliver died at 93, he left behind more than just a personal legacy. He willed the bulk of his estate, through his private foundation, for need-based scholarships. Unable to afford college as a young man, he wanted to ensure future generations could pursue their own ambitions. His foundation also provides funding for the children's room at Abbot Public Library, a quiet but lasting contribution to the community he had come to call home.