All in all, he wasn't much of a soldier.
Edward Bailey was added to the muster rolls of the 63rd Regiment of Foot on 21 February 1777, when the regiment was in the New York area. The circumstances of his joining are not known. He may have been an American, or an "old countryman" already in America; he didn't join at a time when other recruits from Great Britain joined the regiment. It didn't take him long to get into trouble.
On 25 June 1777, the regiment was assembled on the parade of their encampment, and Bailey was missing. On the night of 30 June, he showed up at the hut of a wagoner who worked for the army. The wagoner suspected that Bailey was a deserter, and "entertained" him until soldiers came and put him under arrest.
Put on trial for desertion three days later, Bailey pleaded that he had not intended to desert, but that he had "made away with some necessaries," that is, shirts and stockings, presumably of fellow soldiers. Fearing punishment for this theft, which could have been as much as a few hundred lashes, he "wandered about, and lay in the Fields." He said he intended to return to the regiment on the night he was captured.
Bailey's alibi was common one, and was effectively an admission of guilt - regardless of his intentions, he had in fact deserted, and the only basis the court might have for mercy was the fact that he'd expressed an intention to return and did, in fact, go to a person who worked for the army. Desertion was punishable by death, so Bailey probably was simply hoping for a more lenient punishment. If that was the intention of his defense, he succeeded. The court found him guilty, which he clearly was, and sentenced him to 1000 lashes, a standard corporal punishment for this crime.
Then Bailey caught a break. Sentences of general courts martial were subject to approval by the local commander in chief. In this case, General Sir William Howe determined that there was "a certain want of form in part of the proceedings" of the trial. It is not stated what was lacking; perhaps it was because the prosecution didn't ask whether Bailey's tent and knapsack were examined to determine what possessions he taken, or that no witnesses were asked whether he'd been enlisted properly, or because no statements were made about whether he'd resisted being arrested, or Bailey's statement about having stolen some clothing wasn't pursued. All of these things were typically brought up in desertion trials, but were either omitted or barely touched upon in Bailey's trial. Whatever the reason, the punishment was remitted, and Bailey was released to return to duty.
Seven months later, Bailey was on guard duty on the British lines outside of Philadelphia. He was in the guard room at a quarter to two o'clock in the afternoon of 5 February. He was among the men scheduled to go on duty at Redoubt Number 8, and they were ordered to take their provisions with them, but when roll was called at three o'clock, he was gone. His musket and bayonet were in the guard room, but not his blanket or cartridge pouch. By the next day he was still nowhere to be found, so his absence was reported to the regiment's adjutant.
Two days later, 8 February, the adjutant received a tip that Bailey had been seen at a house a couple of miles away from the 63rd Regiment's quarters. A serjeant and a soldier went the next day to search for him. When they got to the house, they learned that Bailey had been there but had just left only a half-hour before. The searchers noticed footprints in the snow and followed them to another house, still farther from their quarters, where they found Bailey. They asked him why he'd left. He explained that he'd left his cartridge pouch and blanket on a bush, and that when he returned for them they were gone, and he was afraid to go on duty without them.
The following week Edward Bailey was put on trial once again. The serjeant who discovered his absence, the two men who found him, and the adjutant all gave testimony from which . Bailey called no witnesses in his defense, but told the court that he had had no bread to take with him when he was ordered out for duty in the redoubt; he went to town to get some, but on the way he left his blanket and pouch under a bush. When he returned, his things were gone, and he was afraid to return to the guard or to the regiment without them. He went to a house and stayed there for four day, but "being then almost starved, he went in search of a bit of bread." Unable to find any, he was returning to the regiment when the searchers found him.
This story had some similarities to his previous one. This time the court obtained a few more details: the guard had indeed been ordered to take provisions with them on the day Bailey deserted, the blanket and cartridge pouch were missing and never found, and Bailey's path in fact led away from the regiment, not towards it. His previous trial was also mentioned, and the fact that he hadn't been punished.
There was really no question of guilt; Bailey himself admitted to having gone off. The court's issue was to determine a sentence. Had Bailey intended to desert, or was he genuine in saying he'd intended to return? It was truly the difference between life or death. The court chose the former, and sentenced Bailey once again to receive 1000 lashes. This time there was no want of form, and no reprieve from the punishment. We don't have explicit information about whether and when the lashes were administered, but we do have a clue that they were: Edward Bailey deserted yet again on 2 August 1778, this time never to return.
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