When the Institute of Play set about creating a new public school in New York City in 2009, its focus was on using the intrinsic qualities of game design and play to reimagine what learning in the 21st century might look like for young people. Three years and another new school later, all parties remain standing, despite the high number of collisions that occurred between vision and reality along the way. This talk will explore the art of the pick and roll as a metaphor for what happens when game design and learning collide.