The Nachem prayer for tisha b'av describes he city as השוממה מאין יושב, "desolate without inhabitant." What does this mean? In what way was Jerusalem desolate without inhabitants? Does this have a non-literal meaning? NOTE: I am not referring to the question of Nachem after 1967. I am asking what this prayer could have meant for the nineteen hundred years beforehand.
Two thousand years beforehand, they may not have said this text.
Rambam's text, for example, does not have it, nor do Seder Rav Amram Gaon (ed. Harpenes: Seder Tisha B'av), or Seder Rav Sa'adya Gaon, which just has השוממה.
Nevertheless, it is present in the Siddur of R. Eleazar Rokeah (ch. 123 p. 637). His Siddur makes clear that the references to being bereft of its inhabitants refer particularly to the Jewish inhabitants.
והשוממה מכל טוב. האבלה מבלי בניה שאין ישראל בתוכה, דרכי ציון אבילות מבלי באי מועד...והשוממה מבלי יושב אין איש מיהודה יושב בה, כל שעריה שוממין. היא יושבת בגוים
Desolate of all good. That is in mourning without her children: for the Jews are not in it; "The paths of Zion are mourning, without pilgrims." And bereft with no inhabitants; there is no man of Judah living in it: "All its gates are destroyed."
The line השוממה מאין יושב is thus particularly understandable in light of the line: ויבלעוה לגיונים, ויירשוה עובדי פסילים; that it was occupied by foreign legions and idolaters.
This prayer referencing general destruction, absence of Jewish inhabitants, and occupation by foreign armies was always true to one degree or another following the destruction of the Second Templ, until modern times. For example, following the destruction of Jerusalem (in 70), Josephus writes (The Wars of the Jews: Book VII:1):
Now as soon as the army had no more people to slay or to plunder, because there remained none to be the objects of their fury (for they would not have spared any, had there remained any other work to be done), [Titus] Caesar gave orders that they should now demolish the entire city and Temple...there was left nothing to make those that came thither believe it [Jerusalem] had ever been inhabited.
Furthermore, the Bar Kokhba revolt 65 years later:
Resulted in the extensive depopulation of Judean communities, more so than the First Jewish–Roman War of 70 CE. According to Cassius Dio, 580,000 Jews perished in the war and many more died of hunger and disease. In addition, many Judean war captives were sold into slavery. The Jewish communities of Judea were devastated to an extent which some scholars describe as a genocide. (Wikipedia).
Furthermore, Jews were barred from entering Jerusalem except for on Tisha B'av (ibid). They remained banned throughout the remainder of its time as a Roman province, except during a brief period of Persian rule from 614 to 629. (Wikipedia)
Later, during the First Crusade, Jerusalem was captured by Christians in 1099, and:
The capture was accompanied by a massacre of almost all of the Muslim and Jewish inhabitants (Wikipedia).
According to the Muslim chronicle of Ibn al-Qalanisi, "The Jews assembled in their synagogue, and the Franks burned it over their heads. (Wikipedia)
This period lasted until the Crusaders were defeated at the Siege and Fall of Jerusalem in 1187. About 30 years later, Jerusalem and its Jewish inhabitants again suffered destruction when the Ayyubid ruler of Syria, Al-Mu'azzam destroyed Jerusalem:
The city suffered two waves of destruction in 1219 and 1220. This was absolute and brutal destruction, with most buildings in Jerusalem and its walls destroyed...The vast majority of the population, including the Jewish community, left Jerusalem. (Wikipedia).
From 1229 to 1244 the city was returned to mostly Christian control, by Abassids allied with them. In the Siege of 1244, however, As-Salih Ayyub who not allied with the Crusaders, summoned a huge mercenary army of Khwarezmians, who proceeded to again, destroy the city.
In 1260, after the city is retaken by the Ayyubids from the Khwarezmians, it is raided by Mongols. (Wikipedia)
Almost a decade later, when Ramban moved to Jerusalem, he is reputed to have found just two Jewish families (Wikipedia).
While the population grew with time, even 200 years later, in the late 15th century the Jewish population of Jerusalem varied from 76-250 families (Wikipedia). Following a "mass" migration led by Yehuda Hassid (see here about him and his synagogue) in 1700 (when the Jewish population was about 1200), the Jewish population rose to 2000 by 1723. (AFAIK the highest it was since the destruction of temple, and probably just a fraction of a percent of its population then). By the early 19th century, its Jewish population was no higher. After multiple waves of immigration, and significant philanthropic efforts on behalf of residents, the population reached 10000 at the end of the 19th century, and rapidly grew to almost 100000 in 1944.
While the city wasn't always totally uninhabited, or even bereft of all of Jewish inhabitants, (See timeline) it frequently changed hands among foreign invaders, was destroyed multiple times, banned Jews for centuries, and for nearly two millennia did not return, to even a shadow of its former self (with a Jewish population of hundreds of presumably hundreds of thousands (Tacitus says 600000) before the destruction of the second Temple.).
Alternatively, the Imrei Emmet explains this as referring to the heavenly Jerusalem not being inhabited by God, as it is stated (Ta'anit 5a) that God will not enter the heavenly Jerusalem, until he enters the terrestrial Jerusalem. (Cited in Daf Al HaDaf to Ta'anit 5a).