|“||How was yer first time, Jamie? Did ye bleed?||”|
— Rupert, Outlander
Events of the Novels
In 1743, Rupert agrees to accompany Claire and Murtagh when they try to rescue Jamie from Wentworth Prison. In Wentworth town Rupert plays cards and drinks with the guards from the prison and extracts useful information from them regarding the habits of the prison governor. While Claire and Murtagh visit the prison the next day, Rupert goes cattle lifting. He steals 25 cows belonging to MacRannoch and this gives Claire and Murtagh the leverage they need to persuade MacRannoch to help them rescue Jamie. That night Rupert and the other four MacKenzie men take the cattle to the prison and drive them through the postern door that Claire escaped through and then ride as fast as they can back to the MacKenzie lands.
In 1745, Rupert is badly wounded in a skirmish prior to the Battle of Falkirk Muir with a punctured lung caused by a musket ball going through his chest. He makes it to the safety of the kirk where Claire is waiting out the battle. When Rupert realizes he is dying and that the English are close to capturing the church, he asks Dougal to kill him as he does not want to die at the hand of strangers. Dougal is shocked but agrees to Rupert's wish and stabs him with his dirk.
Claire's first impression on meeting him is that he is a ruffian. He is constantly making ribald remarks, much to the entertainment of his fellows. He is also one of Dougal's best marksman and deemed the best with a dirk.
Rupert is described as a fat greasy man with a black beard.
- Rupert is a Low German form of Robert, grom the Germanic name Hrodebert meaning "bright fame", derived from the Germanic elements hrod "fame" and beraht "bright".
- MacKenzie is the anglicized form of MacCoinnich, a Gaelic patronymic name meaning "son of Coinneach". The personal name Coinneach means "handsome" or "comely".
- In the Outlander television adaptation episode Vengeance is Mine, Rupert's story deviates from the novels. Instead of dying in the church from a punctured lung, Rupert survives and only loses an eye. His reprieve proves temporary, however; within days of the Battle of Culloden, Rupert is executed as a traitor, along with nearly every other Jacobite soldier.