How can vibrant, contemporary art be produced that deals with vibrant, contemporary mathematics? To address this question, a collaboration began between an artist (Schuh) and a mathematician (Devadoss), revolving around recent problems in phylogenetics and the space of evolutionary trees. The result was twofold: First, a triptych of paintings was created, using acrylic, graphite, watercolor and metal leaf, that focused on different navigations within this tree space. Second, a novel set of open mathematics problems was discovered solely as a result of this investigation.