Abstract: A striking tool assembly comprises a tool head including a tool eye having disposed therein a sleeve member for receiving an elongated tool handle to perform a manual tool work operation. A flexing structure enables the annular wall structure of the sleeve member to temporarily collapse inwardly for a retaining section to be located in a sleeve securing position when the sleeve member is moved in a longitudinal axial direction into the tool head eye. The sleeve member includes a tool eye mating portion and an overstrike portion. The tool head system comprises a plurality of tool heads each of which is effective to perform a different manual work operation. The sleeve member of each tool head assembly has an inner tapered bore including an inner frictionally mating surface effective to frictionally mate with a preselected elongated tool handle, which may be used interchangeably with each tool head of the tool head system.