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.
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In December of 1849, Lieutenant Jack Wilkes spent Christmas with the Smedberg family on his way to join the USS Marion. He will be at sea for almost three years in the Pacific. From that year on until 1851, Jeanie spent every summer with the Wilkes family in Washington, DC. During this time she met Stephen A. Douglas; Harriet Lane Johnson, niece of President James Buchanan; Sophie Alexander, Mrs. Andrew Jackson, and General Jack Gibbon.