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The gate we see and use today is the work of Sulieman the Magnificent, from
the 16th century after the conquest of the Ottomans. Beneath it are remains of
the earlier Roman and Herodian gateways and some suggestions of remains from
much earlier periods. It is likely that the Hadrianic gate, from the 2nd century
CE, of which we have considerable archæological evidence, was free-standing and
not a part of the wall, making it resemble very much the "Triumphal Arch" idea
so beloved of monumental Roman society and architecture; this would sit well
with a possible eastern approach to the city wall, or at least a market place,
where, in today's Via Dolorosa we have the remains of another "Triumphal Arch" -
that which has become known as the "Ecce Homo" arch. During the late Roman, on
into the Byzantine period - especially the reign of Justinian (6th century), the
Damascus Gate led through to the Cardus Maximus and Cardus
Secundus, two of the major streets in developed Byzantine cities.
David
Roberts' lithograph shows the gate as it was during his visit in the middle of
the 19th century. Much of what we know today was completely hidden from his eyes
but, as usual, he manages to convey with realism and elegance the atmosphere of
his times.
You may like to compare David Roberts' lithograph with a more "recent" rendering. If you look closely you can see in the shadows, the arched, eastern opening to the Hadrianic entrance below level to the left of the foot-bridge which was hidden from David Roberts.