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Organisations operating in today's market are facing an upcoming shift in workforce demographics. A majority of today's current workforce belong to the Baby Boomer generation (individuals born between 1946 and 1964). Many of these workers have already reached retirement age with many more reaching retirement age in the near future. The workers who are next in chronological line to fill the vacancies created by these departures belong to Generation X. There has been much speculation in the popular press concerning these workers, their work histories, and their workplace expectations. There has also been extensive study of the employment relationship (the psychological contract), a worker's assessment of that relationship, and the outcomes associated with it. However, there is no model directly tying worker experiences to the psychological contract and in turn outcomes of the psychological contract. This case study applied qualitative and quantitative methodologies to investigate the role work experiences play in the formation of the psychological contract with a present employer and the outcomes associated with it. Survey data were collected and in-depth personal interviews were completed with 66 Generation X middle level managers working for one of Canada's top employers competing in the knowledge sector. Findings suggest that several key work experiences in the labour market as well as experiences with a present employer are influential in perceptions of the relationship employees have with their employer, how they assess that relationship, and ultimately the outcomes of engagement and trust. The study concludes with: (1) a model illustrating the relationships between workers' experiences and the psychological contract process, and (2) a typology of worker types based on the effects of previous work experiences and perceptions of experiences with a current employer.