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The principality of Moldavia emerged under a Vlach warlord named Dragoș in the middle of the 14th century as a frontier state between Hungary and the Mongolian Golden Horde Khanate. It survived until the middle of the 19th century, when it was merged with Wallachia and thereby became one of the three (along with Transylvania) main components of the modern nation of Romania. Its easternmost region, Bessarabia, was absorbed by the Russian Empire in the 19th century. Most of that region was eventually incorporated as the Moldavian Soviet Socialist Republic, the precursor to the modern state of Moldova, though its southern region became part of Ukraine.
I mention this background to note that Stephen III of Moldavia (d. 1504), whose military victory we’re here to commemorate, is nowadays considered a national hero in both Moldova and Romania. Stephen, who ruled Moldavia from 1457 until his death and is known as “Stephen the Great and Holy” if you’re into that sort of thing, is said to have fought dozens of battles against all comers during his reign, and only lost two of them. He defended tiny Moldavia against every surrounding power that threatened its autonomy and/or its prosperity: Hungary, Poland, the Mongols, and, most especially, the Ottomans. Stephen was among the first European rulers to take on and defeat the Ottomans after the fall of Constantinople—although, struggling to fend off threats from both the Ottomans and the Poles, he eventually wound up paying tribute to Constantinople in exchange for guarantees of Ottoman non-aggression.
Stephen's victory over the Ottomans came at the Battle of Vaslui, fought on January 10, 1475, and is considered one of the highlights of his impressive military career. The immediate cause was a dispute over neighboring Wallachia—Ottoman Sultan Mehmed the Conqueror thought Wallachia was in good hands under his clients, first Radu the Handsome (who was Vlad III Dracula’s brother and Stephen’s cousin) and then Basarab Laiotă the Old, but Stephen disagreed. Really, the fight was over the Bessarabian coast, and specifically the fortresses of Chilia (modern Kiliya, in Ukraine)—which was at one time Wallachian, then Moldavian, then Hungarian (Transylvanian, technically), then Wallachian again—and Akkerman (modern Bilhorod-Dnistrovskyi, also in Ukraine). Stephen had allied with the Ottomans to get Bessarabia back from Wallachia, then turned on the Ottomans when Wallachia became their vassal and Bessarabia thus came under their control. I get a headache trying to parse this stuff, so let’s say that medieval Bessarabia was a Land Of Contrasts and leave it at that.
The region was important, obviously, or else it wouldn't have been so highly prized. For one thing there was its commercial value, sitting as it did along the Black Sea coast. Chilia was especially important, because it controlled the point where the Danube River empties into the sea. Strategically, Ottoman control of Bessarabia opened all of Moldavia to their armies, and Moldavia in turn was an ideal staging point for an invasion of Hungary and/or of Poland—or of the Ottoman Empire, come to think of it, if you were going in the opposite direction. For both offensive and defensive reasons, then, Mehmed wanted Moldavia—or at least he wanted Bessarabia, through which he could control what happened in the rest of Moldavia.
Stephen kept trying to put his own candidate in charge of Wallachia. He had an on-again, off-again alliance with Dracula, who had helped him win the Moldavian throne, only for the two to fall out over control of Chilia. But Radu, who was so enthralled to the Ottomans that there were rumors (questionable at best) that he’d converted to Islam, was Stephen’s real enemy. Stephen actually unseated Radu twice in favor of Basarab Laiotă, in 1473 and again in 1474, but after the second time Laiotă stabbed Stephen in the back and pledged his loyalty to the Ottomans. So Stephen invaded Wallachia again in October 1474 and forced Laiotă to flee. Sorry, I feel another headache coming on.
Mehmed demanded that Stephen knock it off, whereupon Stephen told Mehmed, politely I'm sure, to get bent. So, Mehmed ordered one of his generals, Hadım Suleiman Pasha—who was busy besieging the Albanian city of Shkodër—to finish what he was doing post haste and then march his men into Moldavia to deal with Stephen. This was a serious mistake. Suleiman Pasha’s men had already been in the field for months, and now they had to make a winter march all the way across the Balkans on this new mission. They would be in no condition to fight once they arrived.
The Ottomans outnumbered the Moldavians considerably, but how considerably isn’t entirely clear. Stephen probably had around 40,000 men, but as many as 3/4 of them were poorly armed, poorly trained peasant conscripts. Suleiman Pasha probably had over 100,000 men at his command, but some portion of this was also conscripts, picked up along the way from Shkodër, as well as some 17,000 or so Wallachians, who as we’ll see turned out to be less than reliable. Stephen elected to further exhaust the already struggling Ottoman forces by retreating north and carrying out a scorched earth campaign behind him, forcing them to march even further, without much ability to resupply themselves. The armies finally met outside Vaslui, in an area Stephen knew well but Suleiman didn’t know at all.
This was another Ottoman mistake, and it proved to be insurmountable. The battlefield Stephen chose was a valley, and on the heights and in the forests around it he stationed archers and artillery to strike the Ottoman forces from multiple angles. He used his infantry and light cavalry to lure Suleiman's men into the trap. When Suleiman committed reserves into the valley in an attempt to relieve the men who were being pounded by all that cannon and arrow fire, Stephen ordered an all-out attack from three sides on the confused and bedraggled Ottoman force. The Ottomans broke and ran, and Stephen's army spent the next couple of days chasing them back to Ottoman territory. The aforementioned Wallachians, ignoring Basarab Laiotă’s obligations, refused to fight with the Ottomans and then helped harass their retreat through Wallachia.
Stephen, who had asked other Christian kingdoms for aid before the battle and was given nothing more than a handful of Polish and Hungarian fighters, now sent another appeal for aid along with some of his Ottoman prisoners to Poland, Hungary, and Rome. Owing to his great victory at Vaslui, this time Stephen’s appeal was met with...still pretty much nothing, just like before.
Mehmed was furious, as you might imagine, and made vengeance on Stephen his top priority. After Stephen drove off a raid into Moldavia by the Ottomans’ Crimean Tatar vassals, Mehmed sent a ~150,000 man army north in 1476 that ultimately defeated Stephen (albeit at considerable cost) at the Battle of Valea Albă in July. However, the Ottomans weren’t able to capitalize on their victory, as a combination of disease, Stephen’s harassment, and the arrival of a new army raised by Dracula (who was still contesting rule of Wallachia with Laiotă) forced them to retreat. The Ottomans eventually did capture Chilia and Akkerman in 1484, at which point Stephen agreed to accept Ottoman vassalhood and began paying tribute to Constantinople.