John Gassaway, of the prominent Gassaway family in Anne Arundel County, was a tenacious man whose persistence served him well both during and after the Revolutionary War. As soon as it became evident that the colonists were going to war with Britain for American independence, Gassaway applied for a commission, which he did not receive. Undeterred, Gassaway enlisted in Smallwood’s Regiment as a sergeant, and petitioned the Convention again for a commission in May of 1776.
In the Archives collection of Maryland State Papers, we have Gassaway’s second petition for a military commission. In his letter to the Convention, Gassaway attributed his lack of previous appointment to “being a little stranger to the Majority of the Delegates,” and his consequent “want of friends to mediate on…[his] behalf.” Gassaway pointed to his current enlistment as testimony of his devotion to the American cause, while pushing for a promotion to a commissioned officer stating,
Alas there are now two vacancies in the Companies here in Baltimore for Promotion. I hope you will Endeavor to put me in one of them… you sir are well acquainted with my father and family and I am sure you can use a great deal of influence with the Council of Safety to promote me. Pray do not forget me. 
Gassaway’s persistence was rewarded with a commission as an ensign in the newly formed Flying Camp in June 1776. Gassaway went on to serve in Ramsey’s Fifth Company at the Battle of Brooklyn, earning him a place of distinction among the heroic Maryland 400.
After the conclusion of the Revolutionary War in 1783, John Gassaway returned to Maryland where he worked for a time under his older half-brother Thomas Gassaway, who was Register of Wills in Anne Arundel County. Upon Thomas’s death, John Gassaway petitioned the House of Delegates for appointment as Register of Wills. John was not a resident of Anne Arundel County at the time, which should have made him ineligible for the position, but this did not deter him in the least. Upon being informed that his lack of residency made him ineligible, Gassaway replied, rather presumptuously,
I was informed that the honorable Council were of [the] opinion that I was ineligible for want of residence in this county… I cannot think myself ineligible when all circumstances come to be fully considered.
Gassaway also noted that, “I have not the least wish to [discount] the …services of the Gentleman who is my competition for the office, nor to put myself in comparison with him, [but] my character for integrity is unimpeached.”
In countering objections to his appointment, Gassaway attempted to strengthen his petition by arguing that his motives were of the highest moral caliber. In his petition, Gassaway argued that
I was not urged to ask the appointment from a desire to promote my own interest…more powerful motives influenced my conduct. My Brother has left behind him a Widow and six helpless children without any means for their support and my intention was to apply a great part of the [income] of the office to their maintenance.
Just as he did in his application for a military commission, Gassaway ended his letter to the House of Delegates with dramatic flare, reminding the Delegates that “The bread of the widows and orphans depend on your decision.”
Whether for this reason or for others, John Gassaway was appointed Register of Wills in Anne Arundel County, a position he would hold from 1787 to his death in 1820. Gassaway’s undaunted persistence and tenacity served him well, resulting in both his military commission during the Revolutionary War and his appointment as Register of Wills in Anne Arundel County later in life.
For more information on the life of John Gassaway see his recently created biography here.
 Maryland State Papers, Series A, John Gassaway, Application for Military Commission, 6 May 1776, box 2, no. 35, MdHR 6636-2-35 [MSA S1004-2-565, 1/7/3/25].
 Maryland State Papers, Red Books, John Gassaway to the House of Delegates, 19 November 1787, vol. 31, no. 32, MdHR 4602-32 [MSA S989-46, 1/6/4/34].