Purpose: Based on the social cognitive theory and cognitive-affective system theory, the purpose of this study is to explore how and when paradoxical leadership enhances employees’ bootlegging innovation. To achieve this purpose, the authors proposed a double-chain mediation model in this study. Methods: Data with 342 questionnaires were collected for effective matching between employees and leaders at two time nodes. The hypotheses were validated by structural equation modeling and bootstrap approaches. Results: Results indicate that paradoxical leadership has a significant and positive impact on employees’ bootleg innovation. In addition, psychological capital and thriving at work play a partial mediating role between paradoxical leadership and employees’ bootlegging behaviors respectively and a chain mediating role between the two together. Moreover, there is no significant difference among the three mediating paths. Conclusion: The present research advances our understanding of bootleg innovation with a focus on the specific role of paradoxical leadership. Our findings, and especially those related to the role of psychological capital and thriving at work, reveal the influence mechanisms of paradoxical leadership on employees’ bootleg innovation. At the same time, it is useful for understanding what leadership style can effectively stimulate employees’ bootleg innovation.