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Caleb was born in 1648 in the Bay colony of Massachusetts, he was a foundling who was raised by a puritan family who taught him that self-reliance was a virtue, that it was better to strike out on your own, a lesson Caleb took to heart. In 1687, Caleb died when a tree fell on him and crushed him while he was chopping wood and became Immortal.
He soon learned the ways of the Immortals from Goodman Fletcher. Some years later, Caleb killed fellow Immortal Carl the Hermit, who had taught Duncan MacLeod how to track and survive in the wilderness. Cole, too, would learn all of Carl's knowledge.
In the1970s, Caleb he fell in love and married a mortal who had a son, Joshua, and settled down with her. When she died of pneumonia, Caleb blamed the doctors for her death, and took his adopted son Joshua Cole with him to the mountains in the Pacific northwest where they would live free. They poached animals and killed deputies who were sent after them. Later, a mortal, Eddie Doyle, would join them. The trio began to take control of the forest and killed any trespassers.
In 1992, Tessa Noël was drawing some stone carvings in the forest when she was kidnapped by Cole, Doyle and Joshua. Having taken an interest in her, Cole intended to force Tessa to marry him. Duncan, knowing something was wrong when Tessa did not show up at the expected time, began to search for her in the forest. Realizing that MacLeod was following him, Caleb fled further into the woods. Duncan later got caught by Joshua and then Eddie and decided to jump from a cliff. Alarmed, Caleb broke camp, but not before he unwraped a large and well honed axe. Tessa realized that Caleb was Immortal and confronted him about it. Duncan found Joshua Cole alone and knocked him out.Duncan finally tracked Cole and Tessa with Duncan armed with an axe, Caleb challenged him using his katana. Caleb tells him "First I'll take your Quickening...and then I'll take your woman" and the battle began. During the heat of battle, Caleb revealed that he was Carl's killer. With this information MacLeod mustered up all his anger and with Caleb's own axe in hand, Duncan swiftly beheaded Cole.
Caleb's weapon was a custom battle Axe. However, he is shown to be a very good fighter and is well skilled with Duncan's katana.
- The role of Caleb Cole was played by Marc Singer. Singer was offered the role of Connor MacLeod in the first movie, but he was forced to turn down the role due to scheduling conflicts.
- Caleb's death was the first and only time that Tessa saw MacLeod receive a Quickening.
- Prop duplicates of Caleb's battle axe can be seen hanging on the wall of DeSalvo's Martial Arts. Two of the axes are mounted on the wall outside of Duncan's dojo office.