For most of the year, Bowie had been a lieutenant in the First Maryland Regiment’s First Company, stationed in Annapolis. It wasn’t until July 6, four days before the Marylanders marched for New York, that he was promoted to captain of the Fourth Company. The Fourth had been based in Baltimore all year, and Bowie may not have even met any of his officers or men until a day or two before the regiment departed for New York. In addition, while a full-strength company had 74 officers and men, the unit Bowie inherited had just 58. Bowie was twenty or twenty-one years old, and like all of his men, had no prior military experience.In his will, Bowie made provisions for his friends and relatives “if I fall on the field of battle.” He was to be “interred…at my plantation near Collington in a vault about twenty yards below the vault of my deceased father, in a Direct line with the Garden walk, and this I most earnestly request…should my Body be attainable,” acknowledging the realities of combat which made that an uncertain proposition. Bowie left his “classical books” and “Mathamatical instruments,” items left over from his education in Baltimore, to his stepbrother Philip Sprigg; his other books were to go to his friend and cousin Walter Bowie. In addition, Bowie asked that mourning rings be made and distributed to his relatives and several fellow soldiers. He also freed his “Negro Lad Basil,” a twenty-year-old slave, who likely had been in Bowie’s service for most of both of their lives. 
Perhaps inspired his captain, Joseph Butler, one of Bowie’s lieutenants, made his own preparations. He took aside two comrades, one of whom, Lt. Joseph Ford, later recalled
“[On] August 27, 1776, when Colonel Smallwood’s Regiment was drawn up on Long Island in expectation to engage with the enemy, Lieut. Joseph Butler called Ensign [sic: Lt.] Prall and myself out of the ranks, and desired we remember if he should be so unfortunate as to be killed that it was his desire that his brother or half brother should have his estate…He signified at the time that he did not know where his brother was, or whether he would ever apply [as beneficiary of the estate], as he had not heard from him for some time, and if he should not apply, that Miss Sarah Hall should be possessed of the whole estate…” 
During the battle, the Fourth Company took extremely heavy casualties. Of the 58 men who took the field, just fourteen returned; read more about the Fourth Company’s fate here. With their retreat cut off, the company’s men faced the British in the desperate stand at the Old Stone House. Bowie and Butler were both killed, and many others were either killed or captured. As one of the men, Corporal William McMillan wrote, “My captain was killed, first lieutenant was killed, second lieutenant shot through the hand, two sergeants was killed; one in front of me…my bayonet was shot off my gun…My brother [Sergeant Samuel McMillan] and I and 50 or 60 of us was taken…” 
The Marylanders lost 256 men that day, killed or captured. Poor record-keeping means that we only know who some of those soldiers were. We have identified five who died at the battle: Bowie, Butler, Captain Edward Veazey, Sergeant William Sands (who we featured a few days ago), and Private Thomas Connor. We also know of seventy men who were captured. For a full list see our Battle of Brooklyn Roll of Honor.
The names of all the Maryland soldiers lost at the Battle of Brooklyn may never be learned, just as the final resting place of the Maryland 400 may remain a mystery. For today, however, Daniel Bowie’s will can serve as a reminder of all the Marylanders who died while holding back the British that day in New York.
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2. Will of Joseph Butler, 1777, Harford County Register of Wills, Wills, Liber AJ no. 2, p. 31 [MSA CM599-2, CR 44758]. The quoted passage was recorded by the Register of Wills as a dictated oral will.
3. Letter, William McMillan to Secretary of Treasury, ca. October 1828. Pension of William McMillan, National Archives and Records Administration, Revolutionary War Pension and Bounty-Land Warrant Application Files, NARA M804, S 2806, p. 33-35, from Fold3.com.