This paper examines how teachers in the Indonesian context create motivating conditions for children's learning and development. Sixteen hours of digital visual observations on 38 children (mean age 4.4 years) were selected from a larger dataset of video observations, focus group discussions, and teacher interviews. Using the cultural-historical conception of play as the frame, the findings reveal that in the Playworld, the teachers' 'player' role creates motivating conditions for learning by being inside the play together with children to unify imagination, cognition, and emotion in the play. Imaginary play transforms into experiences where children can learn mathematical concepts and develop self-regulation. This takes place within imaginary play. The teachers' 'player' role creates dynamic interactions for supporting children's learning and development. Therefore, it should be promoted as a new play pedagogy that can encourage degrees of freedom for players and support children's play and learning.