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For Peter, the news that Lewenhaupt's army was leaving Livonia and Courland and moving south, away from the Baltic, was cause for enormous relief. It indicated with reasonable certainty that the Swedish King's ultimate objective was not St. Petersburg, that there would be no combined attack on the Neva by Lewenhaupt from the south and Lybecker from Finland. And with Lewenhaupt out of the picture, Apraxin had enough men to deal with whatever Lybecker might attempt. Accordingly, General Bauer's Russian force of 16,000 men—whose mission had been to watch Lewenhaupt—was now ordered to move south.

Charles' plans now hinged on Lewenhaupt. Critics have blamed Lewenhaupt harshly for his excessive delays, but he could not control the weather. Moving his heavy supply wagons with their great wheels churning in the mud proved almost impossible in the rain, although fascines of brush, branches and wooden boards were laid down. Lewenhaupt was even carrying a portable bridge, the pride of his engineering corps, held together with flexible strips of leather which became so sodden that thirty-two men and to carry each section, and they could carry it only twenty paces before setting it down to rest. In a month, the army moved only 143 miles, an average of less than five miles a day. July stretched into August and then into September, and still Lewenhaupt slowly rumbled and churned his way forward.

Two precious months, July 8 to September 15, the best campaigning days of midsummer, passed while Charles waited. It was not that the supplies themselves were urgently needed yet, but Charles felt that he could not move too far ahead of Lewenhaupt lest the Russian army slip into the gap between the two Swedish armies and catch the smaller force exposed and unsupported. At first, the King had hoped to rendezvous with Lewenhaupt at Mogilev on the Dnieper before the main army crossed the river, and from reports of the lumbering supply column's progress, Charles, pacing impatiently, believed that it must arrive by August 15. But that date came and went and Lewenhaupt still had not appeared. Meanwhile, the army was stagnant and restless. The Golovchin wounded were well again, but the countryside around Mogilev had been eaten bare as thousands of horses grazed the pastureland.

Charles decided that offensive operations must be resumed: not the bold, deep thrust at Moscow that he had planned, but something closer to the Dnieper which would perhaps provoke a battle with the Russians and still, somehow, cover Lewenhaupt. He began a series of maneuvers, marching short distances each day, changing direction—first south, then north—hoping to confuse the Tsar and catch part of his army off guard.

Between August 5 and 9, the Swedish army at last crossed the Dnieper and began moving southeast toward the southern flank of the position Peter had taken on the Smolensk road. On August 21, Charles' army reached Cherikov on the Sozh River to find Menshikov's cavalry already in position on the opposite bank and the mass of the Russian infantry coming closer. With the two opposing armies now in close proximity, their patrols were in constant contact and there were frequent skirmishes. On August 30, a battle of sorts took place. It was not the battle that Charles had hoped for or even expected. The King had camped his army along a branch of the stream Chornyaya Natopa, which bordered a marsh. Roos, commanding the rear guard, was camped on the edge of a marsh three miles away. The marsh was difficult but not impassable, and the Tsar and his officers had quickly learned the lesson of Golovchin: that a marsh could be crossed. At dawn on August 30, 9,000 Russian infantry and 4,000 dragoons commanded by Prince Michael Golitsyn crossed the marsh in a dense morning mist and attacked Roos' camp. The Swedes were taken by surprise, never having before been subjected to a Russian infantry attack. Two hours of fierce hand-to-hand combat ensued before reinforcements from the main Swedish camp arrived and the Russians withdrew, fading back across the marsh. When Charles heard the firing, he assumed that Peter desired a major battle, and the following day the entire Swedish army was drawn up in battle formation. But no attack came, and when Rehnskjold's cavalry reconnoitered the silent Russian positions, he found.

With every day that passed, the problem facing Charles grew more acute. The army was poised, ready for the last great thrust that would end the war, yet it couldn't move forward without Lewenhaupt because the Tsar had scorched the earth bare in the regions ahead. And because of the lack of food, it couldn't simply stand where it was. This left two choices, the first being to retreat to the Dnieper and wait for Lewenhaupt there. Charles rejected this idea. To retrace his steps was repugnant to him—it would confirm publicly that the entire summer campaign had been a failure. Although uncertain as to Lewenhaupt's exact position, Charles believed that he was approaching and that, despite the delays, the rendezvous would soon take place. The second alternative was bolder and therefore more to Charles' liking: a march south, away from Smolensk and Moscow, into the Russian province of Severia. This would maintain the momentum of the Swedish offensive and, at the same time, bring the army into a rich area still untouched by Peter's ravaging, where the fields were just being harvested. Replenished in Severia and reinforced by Lewenhaupt, Charles could then march on Moscow.

After prolonged discussions with Rehnskjold and Piper at Tatarsk, Charles decided to take this course. Once decided, it was urgent that the move be made swiftly and secretly to ensure that the Swedes would arrive in Severia before the Russians. The Swedes had the advantage: Charles was nearer and had the more direct route. If he turned his back on the Russians now and marched rapidly south, he would leave them behind and get there first. Thus, at Tatarsk, new orders were issued to the Swedish army. A special mobile vanguard of 2,000 infantry and 1,000 cavalry—the best of the Guards and other elite regiments—was issued two weeks' rations so it could move rapidly and not have to waste time foraging. Placed under the command of General Anders Lagercrona, it was ordered to hurry by forced marches and seize the towns and river crossings which would open Severia to the Swedes and block it to the Russians. Lagercrona was informed of the overall plan and knew that the objective of the operation was the seizure of the provincial capital, Starodub. The distance from Tatarsk to Starodub as the crow flies was 125 miles. That same night, three separate couriers were dispatched to Lewenhaupt telling him of the change of plan and ordering him to change the direction of his march toward Starodub. The three couriers were sent at intervals during the night to ensure the arrival of at least one.

On the early morning of September 15, the march to the south began, a march fateful in the life of Charles XII and in the history of Peter and of Russia. The advance on Moscow was turned aside—as it happened, for good. Charles' decision at Tatarsk also marked a turn in Sweden's fortunes. In the previous fall and winter, he had marched halfway across Europe, brilliantly maneuvering his enemy out of a series of formidable river barriers. Yet in the summer of 1708, Charles' strategic planning had gone badly awry: he had allowed himself to be chained to the arrival of Lewenhaupt and the supplies. Lewenhaupt had not arrived, and the summer and the advance on Moscow had both been lost. Nevertheless, in September 1708, when Charles stood at Tatarsk and decided to turn south, he still held the initiative. His army was intact. He turned toward Severia with optimism and hope that, if the Moscow campaign had failed, the setback was only temporary.