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In 1841, Jack Wilkes approached his mother about joining the Navy. Although she opposed the idea, Jane Renwick Wilkes sought the help needed to obtain his commission and painstakingly made the uniform for her fourteen-year-old son. His father Charles was still away at sea, and was heartbroken to receive word that Jack was now a Midshipman. Jack served aboard a number of ships that traveled to the South Atlantic, the Mediterranean and Brazil. During the Mexican War, Jack was stationed aboard the USS Mississippi. In 1847, Jack graduated first in his class at the newly formed United States Naval Academy. Two years after one of his tours, Jack celebrated Christmas of 1849 with his Smedberg cousins on Beech Street. He and Jeanie Smedberg agreed to write to one another. This correspondence eventually led to their courtship.