The ancient road leading west to the city of Jaffa also gave its name to Jaffa Street in Jerusalem, and from there it went through the mountains of Jerusalem to the port of Jaffa, which was the main port of the Land of Israel for thousands of years, until the end of the British Mandate period. From here the Christian pilgrims came who sailed to the port of Jaffa and ascended to Jerusalem. From there, merchandise was brought to the most important market in all the Land of Israel - the market of Jerusalem.
By the way, in Arabic the gate is called "Sha'ar Halil," because there the road to ancient Hebron, which is one of its names. This road leads to the cities of Bethlehem and Hebron. This road too, by the way, gave name to the main Jerusalem street passed through to Hebron, one of the main streets in Jerusalem.
During the Crusader period, the gate was also known as the 'Gate of David', named after the Tower of David, the citadel adjacent to it and very well-known.
The gate was built at an angle of 90 degrees, as many gates were in the Ottoman Jerusalem. The reason for this angle was to make it difficult for potential attackers to enter through the gate in a quick attack and to break the running and momentum of such attacking forces.
Only at the end of the 19th century, prior to the Kaiser's visit to Jerusalem, the Turks opened the wall to the wide gate next to it so that the Kaiser's chariot could pass through it ...
It has been said that after the building of the wall was completed, the Turkish Sultan was so pleased with the work, that he ordered to execute the workers. Why he did this, you ask? The Sultan did not want the workers to ever build anything like the walls anywhere else.
Another legend holds that the Sultan ordered the heads of the wall planners to be sprayed and buried here because they left David's tomb outside the wall.
Either way, it's quite a tragic ending ...