Mary Fleming's mother, Janet Stewart, was an illegitimate daughter of James IV, and thus an aunt of Mary, Queen of Scots. Janet Stewart was appointed by Mary of Guise to be a governess to Mary Stuart in her infancy and childhood. Janet Stewart had married Malcolm, Lord Fleming, who died in 1547 at the Battle of Pinkie. Their daughter, Mary Fleming, also accompanied the five year old Mary Stuart to France in 1548, as a lady-in-waiting. Janet Stewart had an affair with Henry II of France (Mary Stuart's future father-in-law); their child was born about 1551.
After the Maries and Queen Mary returned to Scotland in 1561, Mary Fleming remained a lady-in-waiting to the Queen. After a courtship of three years, she married Sir William Maitland of Lethington, the queen's secretary of state, on January 6, 1568. They had two children during their marriage. William Maitland had been sent in 1561 by Mary, Queen of Scots, to Queen Elizabeth of England, to try to get Elizabeth to name Mary Stuart her heir. He had been unsuccessful; Elizabeth would not name an heir until near her death.
In 1573, Maitland and Mary Fleming were captured when Edinburgh Castle was taken, and Maitland was tried for treason. In very poor health, he died before the trial was over, possibly at his own hands. His estate was not restored to Mary until 1581. She was given permission to visit Mary Stuart that year, but it is not clear that she made the trip. It is also not clear whether she remarried, and she is assumed to have died about 1600.
Mary Fleming was in possession of a jeweled chain that Mary Stuart had given her; she refused to relinquish it to Mary's son, James.
An older sister of Mary Fleming, Janet (born 1527), married a brother of Mary Livingston, another of the Queen's Maries. The daughter of James, an older brother of Mary Fleming, married the younger brother of Mary Fleming's husband, William Maitland.
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