Abstract: A multi-compartment insulated container holder includes a body with an upper section for a beverage container or vessel and a lower section configured for receiving a personal item, such as a smokeless tobacco product container. The upper and lower sections are magnetically connected. The upper and lower sections include sidewall extensions with alignment faces, which align upper and lower magnets with the container holder in a closed configuration. The lower section includes multiple pillar wedges in radially-spaced relation on an inner perimeter of a lower section sidewall. The pillar wedges are configured for engaging and releasably retaining a cylindrical container in the lower section compartment.