WIBTAH if I tell my coworker he can't participate in Secret Santa due to his conditions?

As psychologist Dr. Henry Cloud notes in 'Boundaries,' 'We change our behavior when the pain of staying the same becomes greater than the pain of changing.' In this scenario, the organizer is establishing a boundary to protect the administrative fairness of a social event, while the coworker is testing those boundaries to suit his personal comfort level.

The organizer’s resistance stems from a commitment to procedural justice, which ensures that all participants are treated equally. By refusing to make an exception, the organizer prevents potential resentment from other participants who might feel the system is being manipulated. However, the coworker’s request reflects a desire for altruism without the burden of material accumulation, suggesting that his motivations are not necessarily malicious but are disruptive to the group dynamic.

The organizer’s firm stance is appropriate for maintaining order in a self-run office event. To handle future situations more effectively, the organizer could offer a compromise, such as allowing the coworker to participate as a 'secret donor' who is not in the drawing, or simply standing firm on the binary nature of the event while explaining the logistical difficulty of exceptions.