Pundit is a novel semantic annotation tool that allows users to create structured data while annotating Web pages relying on stand-off mark-up techniques. Pundit provides support for different types of annotations, ranging from simple comments to se- mantic links to Web of data entities and fine granular cross-references and citations. In addition, it can be configured to include custom con- trolled vocabularies and has been designed to enable groups of users to share their annotations and collaboratively create structured knowledge. Pundit allows creating semantically typed relations among heterogeneous resources, both having different multimedia formats and belonging to dif- ferent pages and domains. In this way, annotations can reinforce existing data connections or create new ones and augment original information generating new semantically structured aggregations of knowledge. These can later be exploited both by other users to better navigate Digital Libraries and Web content, and by applications to improve data management.