This thesis is a study of the fortunes of members of the Scottish Highland military elite during the seventeenth century Interregnum. During the seventeenth century, many members of chiefly military retinues were forced from a position of prestige to that of ‘broken men’. This study has sought to demonstrate that perpetrators of violence during the Interregnum were members of a privileged class who were struggling to maintain this position of privilege. The principal qualification for the subjects of this thesis is that they were of noble lineage. They have been classified as ‘tories’ in order to capture the change that their social group was experiencing. Throughout the thesis, their involvement in military expeditions against the invading Cromwellian army has been discussed and an attempt has been made to discern their motivations for alliance with the royalist cause. Their involvement in other lawless activity that posed a threat to the security of the Cromwellian administration has also been discussed. The policies implemented by Oliver Cromwell, General George Monck and other Cromwellian administrators in order to contain toryism have been analysed. It has been shown that Cromwellian policy tended to the isolation of tories from their chief and accelerated their move from the status of privileged members of the clan gentry to that of outlaws. This thesis also involves analysis of the cultural environment in which tories lived in order to show that the incentive to continue with a violent lifestyle was great. This conclusion has been reached by means of study of Gaelic literary sources. Literary sources have also provided the key to understanding the manner in which Scottish Gaelic society treated tories and have served to highlight their declining public image. To conclude, this thesis is an analysis of change as it affected a certain class of Highland society. Focussing on tories serves to assert the importance of the warrior class to Highland society and to show that the decline of the warrior society was a difficult process that involved great social dislocation. Concentration on the Cromwellian regime serves to highlight the importance of a brief period of government to this seventeenth century process.