By 995 the war between the Byzantine Empire and Tsar Samuel of Bulgaria had been grinding on for nearly two decades. Basil II had failed catastrophically at the Battle of the Gates of Trajan in 986, and after a long civil war against rebel generals he had finally turned his full attention to reclaiming the Balkan territories Samuel had been steadily eating. Year by year, through small sieges and small ambushes and slow attrition, the Byzantine emperor was forcing the Bulgarian tsar onto the defensive. Then in 994 a crisis broke out in northern Syria - the Hamdanids of Aleppo were besieged by the Fatimids - and Basil had to ship his main field army across to Anatolia. He left command in Thessalonica to Gregory Taronites, the doux, and trusted him to hold what had been gained. Samuel saw the gap, and moved.

The Bulgarian tsar did not march on Thessalonica directly. He understood the city's walls were beyond his ability to storm without a navy, and the Byzantine garrison was strong. Instead he sent a small detachment toward the city, deliberately visible, deliberately tempting. The main body of his army hid in the surrounding country and waited. The bait worked exactly as Samuel hoped. Gregory saw the raiders, sent his son Ashot with a small force to track them and gauge the size of the threat, and prepared to follow with the main garrison force when the situation clarified. The Byzantine plan was sound on paper - find the enemy, fix him, force a fight on ground of Byzantine choosing. The plan assumed the enemy was an opportunistic raiding party. The enemy was a tsar with most of his army hidden in the trees.

Ashot fell first. His reconnaissance force was surrounded and overwhelmed. He himself was taken alive - prisoners of his rank were valuable. Gregory, hearing what had happened to his son, did the thing fathers do. He took the rest of the Thessalonica garrison and rode hard to find Ashot before he could be moved. The Bulgarians let him come. They staged a feigned retreat, drawing the Byzantine column deeper into ambush country, and when the trap closed Gregory found himself surrounded with no good ground to fight on. He was killed in the fighting. The Byzantine relief force was destroyed. The garrison of Thessalonica was now badly weakened and the doux was dead.

Ashot's story has an unexpected next chapter. Taken to Bulgaria as a prisoner, he was treated less as captive than as prize. Samuel married him to his own daughter Miroslava and named him governor of Dyrrhachium - the great port on the Adriatic coast that controlled the western terminus of the Via Egnatia. It was a lavish gesture, designed to bind a noble Byzantine family into the Bulgarian elite. Ashot accepted the arrangement, took up his post on the coast, and then quietly arranged Byzantine ships to evacuate himself, his wife, and the garrison. He sailed to Constantinople and arranged for Dyrrhachium itself to be handed over to imperial control. Whether Miroslava had any voice in this we do not know; the chronicles record her movements but not her opinions. Samuel had lost his son-in-law, his hostage, and a strategic port in one act.

Gregory Taronites' successor at Thessalonica was John Chaldos, who in 996 fell into a similar Bulgarian ambush and was also captured. The pattern repeated because the geography rewarded it - the country around Thessalonica was good ambush ground, and Bulgarian commanders had learned how to use it. Samuel pressed his advantage south into central Greece, sacked Salona and Galaxidi, killed or enslaved their populations, and reached Corinth before turning back. The Byzantine general Nikephoros Ouranos finally caught and broke him at the Spercheios river in 997, but the war ground on. It would not end until 1018, at Dyrrhachium - the same city Ashot had handed over - when the last Bulgarian resistance collapsed. By then Basil II had earned the name history would remember him by: Bulgaroctonos, the Bulgar-slayer. Today Thessalonica is Greece's second city, the White Tower on its waterfront a few hundred years younger than this fight, the Roman walls that protected Gregory's garrison still standing in fragments above the modern streets. The hills where his column was destroyed are now suburbs.