Captain Jerome is the Harbour Master's friend. He is also the Harbour Master's old sea captain.
- He is played by Captain Bill Stewart, a tugboat captain with 40+ years of experience working on Tugboats. He also had an additional nine years as a 44-foot motor lifeboat Coxswain in the Canadian Coast Guard. He, his wife Fran, and Bob Henneberry of Sambro were the original crew on the life size replica of Theodore.
- The picture of him and The Harbour Master was taken during the launch of Theodore Too in 2000.