In his late teens, he enlisted in the United States Army, where he served in the Medical Corp during World War II. He was stationed in the US and European theatres of operation for four years. After returning from his tour of duty, he joined the family shipping business. With extensive training and years of experience, he became a Master Mariner and an owner of Kirkconnell Shipping Company. Life at sea during those days was filled with the risks presented by unpredictable weather, long tiring work, and many weeks away from your loved ones. In spite of the known danger, including knowing his own father had lost his life at sea, Captain Jr. and his crews would set sail to bring essential supplies to the people of the Cayman Islands. They brought building materials, food and medicine, and they brought mail to provide a way for the islanders to communicate with loved ones abroad. Their ships and the businesses who received supplies from the ships provided jobs for many Caymanians.

In his late teens, he enlisted in the United States Army, where he served in the Medical Corp during World War II. He was stationed in the US and European theatres of operation for four years. After returning from his tour of duty, he joined the family shipping business. With extensive training and years of experience, he became a Master Mariner and an owner of Kirkconnell Shipping Company. Life at sea during those days was filled with the risks presented by unpredictable weather, long tiring work, and many weeks away from your loved ones. In spite of the known danger, including knowing his own father had lost his life at sea, Captain Jr. and his crews would set sail to bring essential supplies to the people of the Cayman Islands. They brought building materials, food and medicine, and they brought mail to provide a way for the islanders to communicate with loved ones abroad. Their ships and the businesses who received supplies from the ships provided jobs for many Caymanians.