Located next to the Tower of David, one of the best-known sites of the old Ottoman city of Jerusalem, Jaffa Gate was inaugurated in 1538 as part of the rebuilding of the Old City walls by Suleiman the Magnificent, the tenth and the longest-reigning Sultan of the Ottoman Empire.

It is one of its seven gates with its outer gate oriented in the direction of Jaffa Road that leads to the port of Jaffa. Designed to restrict the speed of advancement of the possible invaders, the gate has an imposing entryway that bends at an abrupt right angle. Until the end of the19th century, the doors of the gate, made of iron plated-wood, used to be closed every night to protect the city and the residents of Jerusalem. There is an upper combat compartment above the gate,called the Mashikoli, which was used by the guards as the watchtower and to spill hot oil on the unwanted guests. An inscription carved on the doors depicts the praises of Allah and the Sultan Suleiman the Magnificent, who built the gate and the walls of the old city.

However, the name Jaffa Gate is now used to indicate both the historical Ottoman gate and the wide gap in the city wall adjacent to it to the south. The breach in the wall was made in 1898 to enable German Kaiser Wilhelm II to ride into the city with full of grandeur and ceremonial pageantry.

In Arabic, the name for the gate is Bab Al Khalil, which means the Gate of the Friend and refers to the holy city of Hebron, known as Al Khalil in Arabic. Since by tradition the burial site of Ibrahim or Abraham is in Hebron, the Arabic name for the Jaffa Gate stands for the Hebron Gate. However, in Hebrew, the gate is called Sha’ar Yafo or Jaffa Gate, as it was the beginning of the old road to the port city of Jaffa.

In medieval times the Arabs believed that the room atop the Herodian tower stump represented the private chamber or the prayer room of Prophet Dawud, which is mentioned in the Holy Quran. As King David is in known as Dawud in Islam, they used to call the gate Bab Mihrab Dawud or the Gate of David’s Sanctuary.

Two unimposing tombs are lying just inside the gate, behind an iron grating on the left. According to local legend, they belonged to the two architects, commissioned by Suleiman to construct the Old City walls.

It is said that the architects earned the wrath of the Emperor, as they had left Mount Zion and the tomb of King David without his permission. The enraged Emperor ordered them to be executed and had them buried inside the walls next to Jaffa Gate, in appreciation for their impressive performance in constructing the massive wall.

A 13 feet tall decorated clock tower, built of limestone quarried from the nearby Zedekkiah Cave, was constructed on top of Jaffa Gate' historical gate tower in 1908, topped by four clock faces, conformed to the cardinal directions. While the eastern and western faces showed official European time, the northern and southern faces showed the local time. There was a bell, along with the crescent-and-star symbol of Ottoman rule, above the faces of the clock. However, the Turkish clock tower lasted only for a decade and was knocked down by the British in 1922, as they considered the clock tower to be an unaesthetic. In their further attempt to preserve Jerusalem's historic panorama, they again demolished the row of houses erected against the outer face of the city wall leading down to Jaffa gate from the north in 1944.

During the Arab-Israel War in 1948, that followed the Israeli Declaration of Independence, Israeli forces fought hard to connect the Jewish Quarter of the Old City with Israeli-held western Jerusalem by controlling the Jaffa Gate. But, despite their best efforts, they could not gain control of the gate until the Six-day War in 1967.

An expensive project to renovate the length of the Old City walls began in 2007 and as a part of the project, the restoration and cleaning process of Jaffa Gate was completed in two months by the Israel Antiquities Authority in 2010. The cleaning process included replacing the old broken stones, cleaning the walls of decades of dirt and stains created from the car exhaust and carefully reattaching an elaborate Arabic inscription on the gate during its original dedication of the gate in 1593. However, the bullet fragments in the gate were preserved as the bitter remembrance of the Arab-Israel War in 1948.