The obvious candidate to paint David Lindsay would have been his fellow Scotsman, Allan Ramsay, who was also Reynolds’s chief artistic rival during the 1750s. Lindsay's choice of Reynolds in 1759 reflects a family quarrel that had begun earlier that decade. In 1752, Lindsay’s sister Margaret had eloped with Ramsay to become his second wife, much to the disapproval of her grandiose family. They felt that the humbly born painter Ramsay was an unsuitable match for their daughter. Lindsay’s patronage of his brother-in-law’s younger English rival reveals the tension between the families. They were not reconciled until after 1763 at the death of Margaret and David's father, Sir Alexander Lindsay.