The united Irishmen simply had not the capability to take on the British Empire in an open war, but maybe they could engage them in local battles, but even for this, they would need to be cunning and out-think their adversary. Dr. John Esmonde was just the person needed, a shrewd military tactician. He knew that although he had at hand a very large group of rebels that were waiting on instructions to attack the strong garrison at Prosperous, he still did not hold out much hope of success, based on the firepower of the troops.
On 23rd May 1798 (The evening of the battle of Prosperous), Dr. Esmonde, a Lieutenant in the local yeomanry, but a commander of the local United Irishmen and Fr. Anthony Higgins joined Captain Richard Swayne at a local Inn in the village. The dialogue was mostly centred on the imminent rebellion in the area, as reported by the crown spies. Swayne was somewhat confident that his actions had sent a clear message to all those who should think of rebelling against the crown that theirs was a hopeless case. Father Higgins, simply wanted no more bloodshed and was there to protest over the burning of the Catholic Church, two days earlier.
Dr. Esmonde had already made plans with the Prosperous United Irishmen for an attack on the barrack that very night. He was aware that the rebels had been gathering during the day at the 18th lock on the Grand Canal in Landenstown.
During the course of the evening both Fr. Higgins and Dr. Esmonde assured Swayne that he had indeed broken the spirit of the revolution. That not only would the rebels’ surrender their arms, but they would repent and ask for forgiveness. Swayne was simply being lured into a false sense of security and that his tyrannical brutality had finally prevailed.
Meanwhile the rebels (500 strong) were waiting on Dr. Esmonde’s return with word of how the meeting with Swayne had gone- as the element of surprise was critical if there was to be any chance of a victory.
The rebels simply had not the weaponry or training to engage the crown forces in the field and this proved to be the case at Vinegar Hill and Ovidstown which were to follow.
Dr. Esmonde managed to convince Swayne to allow the locals to surrender their weapons under the cover of darkness so they would not be recognised, for fear of retribution. This he informed Swayne was the only condition he believed the locals would agree to.
Furthermore, Esmonde insisted that if the rebels noticed any soldiers in the streets, he feared they would only turn away and the opportunity would be lost. Heeding the advice of Dr. Esmonde, Swayne agreed to post only two sentries on duty and not to challenge anyone entering the village with weapons.Esmonde succeeded in his objectives, by lowering the defensive resistance of the garrison and informed the rebel encampment of so. Still he may have had some doubts, as he decided not to accompany the rebels into the village that night, but instead he waited on a hill above the village for word of the battle.
The attack on the barrack and the abandoned cotton factory, where the soldiers quartered began at 2:00am on the 24th May 1798.
Here we have mapped out the two routes that the rebels took to Prosperous from their camp at the canal on the 18th Lock. This was one of the more carefully planned attacks by the rebels in all of 1798.