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Drawing upon social comparison theory, we tested a model in the investigation of potential coworker negative reactions toward employees with high proactive personality. We theorized that a focal employee’s proactive personality is positively related with his or her high relative standings in the group, which in turn exposes him or her being the target of coworker envy. This may then reduce the focal employee’s received help from coworkers and give rise to coworker social undermining. We further reasoned that employee prosocial motivation moderates the serial mediated relationships. Our hypotheses were generally supported in three field studies involving a total of 1069 employees nested within 223 groups. Proactive personality was negatively and indirectly related to received help from coworkers, via relative leader–member exchange (RLMX) and relative job performance, and then via being envied by coworkers (Study 1). Results also generally supported the positive and indirect effect of proactive personality on being socially undermined by coworkers via the same set of sequential mediators (e.g., RLMX and then being envied, Study 2). The indirect effects of proactive personality on coworker helping and undermining (e.g., via relative job performance and being envied by coworkers) were only significant when employees’ prosocial motivation was low (Study 3). This research contributes to a more complete and balanced theorization of the influences of proactive personality in organizations.