In 1992, Tessa Noël was drawing some stone carvings in their 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 her expected time, began to search for Tessa in the forest. Realizing that MacLeod was following him, Caleb fled further into the woods. Duncan later got caught by Joshua and the Eddie and decides to jump from a cliff. Alarmed, Caleb breaks camp, but not before he unwraps a large and well honed axe. Tessa realizes that Caleb is Immortal and confronts him about it Duncan found Joshua Cole alone and knocked him out.At the same time, Cole discovered that Doyle had tried to rape Tessa, so he shot him. 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.