Jerusalem of the 15th century was both vastly dissimilar and uncannily alike the Jerusalem of today. As in the rest of the world, the Holy City was beset with the Bubonic Plague, but it was nonetheless a popular place of settlement for Jews across the Diaspora. With the letters of Rabbi Ovadia of Bartenura, we learn of his encounters with Ethiopian, Iraqi, and Indian Jews, and we get a sense of the messianic hopes that marked the times.