First, he got new shoes, and tried them out on concrete. He does not do well running on concrete, ever. He started getting what he thought were shin splints, so he laid off for a few days, then switched back to his older shoes.
Concrete is BAD news.
Puts undo stress on the whole lower extremity boney, ligamentous, muscular. Definitely sounds like anterior compartment, pumping up causing compression. You might even want to check Flexor Hallucis Longus as it sits in the middle down there on fibula and interosseous membrane. It flexes the great toe and aids in plantar flexing the foot. Also Flexor Digitorum Longus as they flex the toes.