Jean Fleming (1553/4–1609) was a Scottish noblewoman and courtier at the court of James VI of Scotland, and a victim of domestic violence.
Jean Fleming was born in 1553/4, daughter of James Fleming, 4th Lord Fleming. Upon his death, his title and estates passed to her uncle, James' brother John Fleming, 5th Lord Fleming, and Jean Fleming had to resort to action in the Privy Council of Scotland to secure a share of the inheritance.
She married John Maitland, then Keeper of the Privy Seal of Scotland and later Lord Chancellor of Scotland, in January 1853. The couple has two children, Anne, born in 1590 and who died in 1609, and John Maitland, a judge who became President of the Parliament of Scotland and of Privy Council. She shared in her husband's work as Chancellor of Scotland. Jean Fleming managed to make an enemy of James VI's wife Anne of Denmark by remarking in her hearing of Anne's supposed relationship with Francis Stewart, 5th Earl of Bothwell, who had been imprisoned for witchcraft in connections with events around the marriage of Anne and James, and whose trajectory from this point forwards was escape, exile, forfeiture and death.
On Maitland's death in 1595 Jean was left a rich widow, and quickly married John Kennedy, 5th Earl of Cassilis, some 22-years her junior, becoming Countess of Cassillis. The age disparity aroused considerable scornful comment in the Scottish court, but Jean's wealth ensured the continued status of the couple: Kennedy was offered a post as Treasurer in 1599, but declined, fearing the cost of the appointment in terms of anticipated loans to a needy James VI.