Born into the clan MacLeod in the Highlands of Scotland in 1518, his father was captured and hanged by the Clan Frazer. In 1536, Young Connor rode into his first battle with his clan, against the Clan Frazer. On the battlefield Connor was 'killed' by the Kurgan, but miraculously recovered after receiving the last rites from Father Rainey. Cursed as a demon, the clan wanted to burn him at the stake, and only the intervention of his friend Angus prevented the clan from doing so. Instead, he was banished from the clan... In 1537, Connor met Heather MacDonald, who's father Angus taught him the art of blacksmithing.

In 1541, a year after Connor and Heather were married, the Immortal Tak-Ne, now Juan Sanchez Villa-Lobos Ramirez, found Connor and taught him about Immortality and the rules of the Game as well as the Gathering. One year later, Ramirez was killed by The Kurgan.

Heather died in 1590 and two years later, Duncan MacLeod was born. In the meantime, Connor moved to Edinburgh and leaned to read and write. It was not until 1625 that he found Duncan rising from the dead on a battle field. Connor became his teacher and fast friend as they he trained his fellow Clansman in Italy. In the 1770s, Connor moved to America to become involved with the American Revolution. He served the Continental army at Valley Forge in Pennsylvania. From there, he continued to take part in battles with the Napoleonic Wars of the early 1800s.

He returned to American in 1855 and soon took part in the American Civil War. Nearly 100 years passed before he met Rachel Ellenstein. In 1943, he rescued the small girl from the Nazis and raised her as his own child. In 1985, Connor defeated the strongest of all the Immortals, the Kurgan, because of the Kurgan's extensive history of taking Quickenings, Connor experienced a brief period in which he thought he had won the Game. This was, of course, not the case. The mortal woman, , was his companion for a while, but he soon returned to his wandering ways.

He eventually settled down in Egypt, adopting a young boy, and was living there when the first rumors of plague came. He packed his bags and his son and took the first flight to Seacouver, to be near his cousin, in case this was a sign of the Gathering. Unfortunately, the boy died shortly upon arrival and Duncan was nowhere to be found.

Then came the dreams. The dreams led him to Mother Abigail's side, and he has remained there as her helper and protector.