The involvement of dignitaries within mass gathering events can often impose several difficult levels of complexity, both during the planning phases and throughout the event itself. Whether the dignitaries are the reason for the mass gathering or they are on location as additional special attendees of the event, so-called “very important persons” (VIPs) such as celebrities, royalty, or major political figures can affect the planning and preparations for medical management contingencies as well as the operational aspects of such events [1–3]. Beyond the typical challenges of mass gathering medicine and protective security aspects, the concepts and practice of executive medicine, concierge medicine, or “protective medicine” pose unique and often unfamiliar and uncomfortable adaptations in terms of delivering medical advice and care. Medically, there is often limited access and reticence to expose the VIP to unfamiliar practitioners. Requests for medications or therapies in the absence of directly seeing the patient is more common. There is also an expectation that the medical care provider will come to see the VIP at the site and not at an off-site medical facility.