Charles Jenkins was introduced to the Great Lakes shipping business upon marrying into the Mack family in the early 1900s, owners of the Mack Steamship Company. Up to this point, Charles had made a name for himself as a lawyer based out in Cleveland, Ohio. When he joined the Mack family, he managed their estate and financial affairs since the former Mack-Becker vessel management relationship was falling apart. In 1902, Mack and Becker separated entirely. Mack took claim over their vessels and Jenkins was hired to manage the vessels. After some years within the industry and learning from his in-laws at the Mack Steamship Company, Charles Jenkins was ready to branch off and create his own steamship company, founding the Jenkins Steamship Company in 1906. 

To kick start his company, Jenkins purchased two vessels from the Mack Steamship Company. After the sale was completed, the two vessels were repainted with black hulls, white cabins, a black smokestack with a silver band and a red “J” at the center. Flying at the pinnacle of the Jenkins’s vessels was this three-foot rectangular flag decorated with a blue border, white background, and a bolded red “J” at the center. 

Although Jenkins had a promising start to his new company, it faced hardships. The fleet was operating with limited financial resources and under poor management by Jenkins himself. In 1911, after a shareholders meeting, Charles Jenkins was removed from his position as president of the company and was replaced by Adelbert T. Kinney of Kinney Steamship Company. Jenkins’ removal was short-lived as he was reinstated in 1912. Upon his return, Jenkins had greater success with the company’s dealings and management over the fleet. The company thrived over the next decade before finding himself in a similar financial situation once again. In 1933, the Central National Bank of Cleveland sued Jenkins for failure to pay a loan of $140,000. With no real source of steady income within the company, Jenkins resorted to selling off his vessels as a method to pay off the debt. The last of his ships were sold in 1936, but fell $6,000 short of paying off the remaining debt. At this point, Jenkins filed for bankruptcy, retired from the shipping industry, and dissolved the company in 1937.