Together with Chalkidike this strong city had remained in Byzantine hands since its recapture from the Franks in 1224, which had ended the shortlived kingdom of Thessalonika. After the mid-14th century, when Ottoman conquests cut it off from Constantinople, the city depended principally on the strength of its massive walls for defence, its armed forces being very small. In 1371 it proved necessary to convert half the property of the monasteries of Mount Athos and Thessalonika into pronoiai and to tax the rest in order to strengthen the city’s defences, but in 1384 its governor (and so-called Emperor) Manuel II, son of Emperor John V, could still put only 100 horsemen in the field according to one source (though this was not his entire strength), and the next year he found it necessary to request 70 mercenary crossbowmen and 200 suits of armour from Venice to assist in Thessalonika’s defence. The Ottomans captured the city in 1387, holding it until 1403, when it was returned to the Byzantines. Its last governors were the future Emperor John VII (1403-8), Demetrios Leontares (1408-15) and one of Manuel IPs sons, Andronikos Palaeologus (1415-23).
Thessalonika was besieged continuously by the Ottomans from 1422 to 1430 and, unable to adequately defend it, in 1423 Andronikos ceded the city to Venice. The Venetians put in a garrison which numbered 700 crossbowmen in 1426, in addition to which they usually landed the crews of any of their galleys that happened to be anchored in the harbour — 5 of them in 1426, and 3 in 1430. In the latter year, which finally saw the fall of the city to the Turks, Doukas reported that its defenders were outnumbered 100 to 1, with ‘barely one crossbowman to cover 10 turrets’. From another source we know that one element of the Venetian garrison on this occasion was comprised of a sinister band of cut-throat mercenaries referred to as the Getarii, who were sprinkled among the citizens and native militia with orders to cut down anyone unwise enough to express a desire to surrender. Although artillery is reported to have been used by the Ottomans in their attack, there seems to be no record of its use by the defenders.