We have treated five patients with metatarsalgia and triggering of the lesser toes. This paper describes a mechanism of triggering that involves a previously undescribed flexor pulley system in the toes that is very similar to the pulley system in the fingers. The specific anatomy of the toe flexor pulleys is described based upon the dissections of 50 fresh-frozen cadaver toes. These pulleys were composed of transverse to obliquely oriented fibrous bands within the flexor sheaths from the metatarsal heads to the distal phalanges. We found a system of pulleys in the lesser toes and the great toe, analogous to that found in the hand. Trigger toe is a rare entity and is only briefly described in the literature. We believe it is more common than is now recognized and may be an important underdiagnosed cause of metatarsalgia. The diagnosis is made when active plantarflexion causes the toes to catch in flexion and the patient is then unable to extend them. Nonsurgical therapy consisting of steroid injection, NSAIDs, or changing footwear may be effective, otherwise surgical release of the A1 pulley may be required.