Previous research has demonstrated that unfairness judgments of resource allocations become more complex when there are more than two recipients. In order to explain some of this complexity, we propose a set of psychological mechanisms that may underlie four different choices of maximally unfair resource allocations (MUA): Self-Single-Loser, Self-One-Loser-of-Many, Self-Single-Winner, and Self-One-Winner-of-Many. From this psychological theory, several predictions are derived and tested in vignette studies involving a total of 708 participants recruited online using MTurk. As predicted by our theory, (1) choices of MUA where there is a single loser were much more common when the allocated resource was of negative rather than positive valence, and (2) the amount of egoistic bias individuals exhibited when judging the unfairness in receiving a small rather than a large share in a non-extreme multi-party allocation was predicted by their choices of MUA. These findings suggest that an individual’s choice of MUA reveals some generally relevant principles of how unfairness is perceived in multi-party allocations. This opens up new lines of inquiry, especially regarding research on social dilemmas and social value orientation.