George Leslie (c.1417-1489/90), first earl of Rothes, inherited a large collection of estates mainly on the east coast of Scotland which made him an important noble in North-East Scotland. He was made a lord of parliament and his support of James II was rewarded with the earldom of Rothes and barony of Ballinbreich in Fife in 1458. However his career stalled in financial problems and difficulties with William Sinclair, earl of Orkney over the annulment of his second marriage, as children of this marriage had married into the Sinclair family. He attended parliament but was not a significant political force. He was ordered by James III to make provision for his grandson and heir George Leslie in 1487 after a rift in the family.
James III obtained the earldom of Orkney and lordship of Shetland in 1472 from Christian I of Denmark-Norway who needed to raise a dowry for his daughter Margaret to marry James. Henry Sinclair was granted a thirteen year lease of Orkney and Shetland, the custody of Kirkwall castle and the offices of justiciar, foud and bailie of Orkney and Shetland in 1488.
Henry Sinclair (c.1480-1513) was the son of Christian Leslie, daughter of George Leslie, first earl of Rothes, and William Sinclair, son of William Sinclair, third earl of Orkney, and inherited the Sinclair properties in Orkney.