The Maitland family came to Britain from France with William the Conqueror in 1066 and originally settled in Northumberland. Through military service and their contributions to Law and the Arts in Scotland, the Maitlands gained in influence and power with John Maitland becoming Lord Chancellor of Scotland and Baron of Thirlestane in 1590. It was John who first built the "T" shaped keep, that forms the central part of Thirlestane Castle, and the four large corner towers along its flanks.

Descendent, John Maitland, the second Earl of Lauderdale, was one of the most important figures in the latter half of the 17th century as a leading Presbyterian, Royalist and chief Scottish adviser and confidant of Charles II. Upon the abdication of Charles II, John spent nine years in the Tower of London under sentence of death. He was released upon Charles' restoration to the throne and made Secretary of State for Scotland where he wielded unrivalled power and influence. Upon his second marriage to the Countess of Dysart, he was granted the title Duke of Lauderdale and transformed Thirlestane Castle into a palace from which to direct the affairs of Scotland. The construction included two new front towers and a grand staircase, which together dominate the approach to the castle. Towards the end of his life, the Duke over-stretched his use of power. Reacting to the strong pressure of most of the Scottish nobles, the English Parliament and the Privy Council, the King forced the Duke to resign all his offices.