Ottoman Empire 1587 - Murad III (Labeled)

I'm very skeptical about whether such an expedition would have had any chance of lasting success.

Manuel Komnenos made far more progress in a similar invasion of Apulia 300 years earlier, launched during a Norman civil war and with many local allies and supporters (one of the armies was mostly central-northern Italian mercenaries, gathered and launched from the allied city of Ancona), but even his armies were eventually pushed out when the Normans formed a somewhat united front and affairs elsewhere demanded imperial resources.

The Ottomans, facing a Christian coalition with no local allies or supporters and held hostage by Venetian control of Corfu, Durazzo, Avlona, Crete, and other important ports in and around the Ionian sea, would have faced an infinitely more difficult task, and with no lack of affairs elsewhere that might similarly demand their resources. I could imagine an Ottoman army sacking a number of towns and cities before being bogged down and retreating, if they were lucky, but the idea that they would be able to establish a permanent toehold seems extremely unlikely, never mind rolling up the peninsula like a latter-day Belisarius.

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