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As a player, he represented the Israel national team three times. As a manager, he took charge of numerous clubs as well as the Israel under-21 team, and the senior national team in 2006–2010.
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. In 1977, after playing for Hapoel Kfar Saba, he became the team coach.
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.