The city of Thessaloniki (formerly Thessalonica) always struck me as one of the ultimate urban runners up in history. It became the most important city in Macedonia…right before the Romans showed up. It became an important Roman city…because it was a way point on the main route from Rome to Byzantium. When the Roman Empire was divided into the Tetrarchy in the third century, it became one of the capitals of the Emperor Galerius…right before Constantine ended the Tetrarchy and established a New Rome at Byzantium/Constantinople. It was the “second city” of the Byzantine Empire. Today it’s the second-largest city in Greece. You get the idea. Nonetheless, Thessaloniki has been an important city since antiquity, and when the Ottomans began expanding into Europe it was one of their earliest targets.