Kashtan started out as a player for Hapoel Petah Tikva. He was the only Israeli player to be called up to the full national team before playing a single match in league play.[3] In 1977, after playing for Hapoel Kfar Saba, he became the team coach.[3]
Kashtan has been called the most successful manager of all time in Israeli football, with six championships, six State Cups and three Toto Cups won under his direction.