This study investigates the concept of flexibility within League of Legends, a popular online multiplayer game, focusing on the relationship between user adaptability and team success. Utilizing a dataset encompassing players of varying skill levels and play styles, we calculate two measures of flexibility for each player: overall flexibility and temporal flexibility. Our findings suggest that the flexibility of a user is dependent upon a user's preferred play style, and flexibility does impact match outcome. This work also shows that skill level not only indicates how willing a player is to adapt their play style but also how their adaptability changes over time. This paper highlights the duality and balance of specialization versus flexibility, providing insights that can inform strategic planning, collaboration and resource allocation in competitive environments.