Margaret gave birth to a girl, Margaret Douglas, in 1515, and soon afterwards her son Alexander died. By then her marriage to Angus was a complete disaster and she soon started taking new lovers. In the meanwhile the child King, her son, was taken from one castle to another by the men who were supposed to protect him, but who just wanted to separate him from his duties, even though these were just a few, as James was still a small child. In 1526 James was imprisoned in Falkland Castle and Margaret tried to rescue him. She even sold some of her mother’s jewels that had surprisingly survived to her extravagant and expensive way of living. Increasingly nervous by the awful business she had done by marrying the ambitious but stupid and violent Angus, she soon forgot of her son’s problems and tried to divorce Angus in order to save her daughter’s fortune and social position.
By then she was already engaged in a love relationship with Henry Stewart (1498-155 , from another branch of the Scottish Royal Family. In January 1528 she obtained the annulment of her second marriage and she married just two months later her beloved Stewart. Probably by the end of that year their only daughter, Dorothy, was born. Dorothy Stewart was the last of Margaret’s children to be born and she died young, apparently in 1547, when her mother was already dead.
In that same year, 1528, James V managed to escape from Falkland and he started his proper reign at the age of 16. His first son, born to his mistress Elizabeth Shaw around 1529, was called James and would be Abbot of Kelso and Melrose. This made Margaret a young grandmother at the age of 39 or 40.
Because of the bad relations between England and Scotland, Margaret Tudor attempted to arrange a meeting between her son James and her brother, Henry VIII, in 1534, but James accused her of betraying secrets and no longer trusted her. In 1535 she asked her son a permission to annul her marriage to Stewart, who had been named Lord Methven, but James refused, astonished by his mother’s eccentric, scandalous and dissolute way of living. In the early 1536 she left Methven and ran away to Stirling with a young lover whose identity is unknown. In April of the same year her daughter Margaret’s behaviour led to another scandal: she married Thomas Howard, half-uncle to Queen Anne Boleyn, who had already fallen in disgrace. To make things even worse, she married without King Henry’s consent, so the couple was thrown in the Tower. Margaret Tudor wrote to her brother asking for her daughter’s freedom, but Henry didn’t even answer, as he thought his sister’s dissolute life had been an example for young Margaret Douglas and that she acted like she did because of what she had seen in her mother’s behaviour. Henry VIII finally freed his niece because she asked for his pardon, alleging that she had been deceived by Thomas, that she was willing for her marriage to be annulled and that she hadn’t consummated her union with Thomas, something which was probably a lie. The marriage was quickly annulled and Thomas would die beheaded in 1537.
That same year, because of her son’s marriage to Princess Madeleine of France, Margaret was forced to live again with Methven in order to keep a sense of decorum in the King’s Court. After attending her son’s wedding she travelled with her husband to Methven, where the couple did find some type of peaceful married life after so many troubles in the past. Margaret was increasingly fat in those years, and she had began more and more susceptible of catching colds. It seems she may have suffered pains and ulcers similar to the ones her brother Henry suffered. Apparently she started drinking too much and her son didn’t even want to hear about her. She died in Methven Castle on November 24th, 1541. Four days later she would have been 52 years old.
James V died a year later, soon after his daughter Mary had been born. His half-sister, Margaret Douglas married in 1544 the noble Matthew Stewart, Earl of Lennox, with whom she had two surviving sons. The eldest, Henry, would become his cousin Mary’s husband (the famous Lord Darnley).