One of the six original gates built by order of Süleyman the Magnificent, Jaffa Gate is actually a dog-legged pedestrian tunnel passing through the city wall (the dog-leg was to slow down any charging enemy forces – you’ll find the same arrangement at Damascus, Herod and Zion Gates). The breach in the wall through which the road now passes was made in 1898 in order to permit the German Kaiser Wilhelm II to ride with full pomp into the city.
Inside the gate, on the left, is the Jaffa Gate Tourist Office. Be aware that the nearby shopfront with the 'Jerusalem Tourist Information Center' sign is a private tour operator, not the official office. The latter is on the corner of Latin Patriarchate Rd.
The Arabic name for the gate is Bab al-Khalil (Gate of the Friend), which refers to the holy city of Hebron (Al-Khalil in Arabic). In Hebrew it is Sha’ar Yafo (Jaffa Gate) because this was the start of the old road to the port city of Jaffa.