Which of the following structures does NOT pass behind the medial malleolus?

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The great saphenous vein does not pass behind the medial malleolus; instead, it runs along the medial aspect of the leg and thigh, eventually draining into the femoral vein. The other structures listed (flexor digitorum longus tendon, posterior tibial artery, tibial nerve, and tibialis posterior tendon) all pass behind the medial malleolus as part of the tarsal tunnel.

Which of the Following Structures Does NOT Pass Behind the Medial