Young Samuel Webb was a legend in his time, a hero of the American Revolution. Some said he was “raised with three silver spoons” engraved with the initials of his three prominent Connecticut families (Webb, Deane, and Saltonstall). Others said he was a good friend, an active, gregarious, and literate young man who wrote engaging letters, and who always made the best of every situation whether good or ill. His grandchildren came to know him as a kind and generous old man, a hero of the American Revolution and a friend of George Washington, Alexander Hamilton, the Marquis de Lafayette, and other notables. In the attic of his home he had a trunk full of uniforms, medals, swords, and letters, protected by layers of blotting paper, which his grandchildren used as playthings: “We were no better than vandals … we tore out pages of those journals and presented pretty little books of blotting paper for our school fellows ….” Webb’s descendants and admirers would later atone for these misdeeds by publishing six volumes of his letters, notes, and diaries, a rich mine of information about the general, his family, friends, neighbors, home town, and the American Revolution. That trove of information enables us to make our own evaluation of this early American hero.
Samuel Blachley Webb was born on December 3, 1753, the second son of prominent Connecticut merchant, trader, and ship-owner Joseph Webb senior (his first silver spoon). Samuel’s mother, Mehitable Nott Webb, was the daughter of a local sea captain. The Webb family lived in an impressive, three-and-a-half story Georgian-style home on Broad Street in Wethersfield, Connecticut. In 1761 when Samuel was eight years old his father died, leaving his family a fortune, a complex set of businesses, and a young, handsome, gregarious, hard-working, politically astute lawyer who took more than a business interest in the young widow. Two years after her husband died, Mehitable Webb married the family attorney, Silas Deane. Thus Samuel Webb acquired the second “silver spoon” of his youth, an impressive new stepfather, tutor, and career counselor. Under Deane’s tutelage the Webb family businesses continued to flourish, and young Samuel Webb gained an exceptional father, friend, and mentor.
Tragedy struck again in 1767 when Webb was fourteen: his mother passed away. His step-father, Silas Deane, was still a young man and in 1769 he married again, this time to Elizabeth Saltonstall, the granddaughter of former Gov. Gurdon Saltonstall of Connecticut (thus Samuel acquired his third “silver spoon”). Silas and Elizabeth built a new home next door to the Webb family home (today both are restored and open to the public). By then the Webb-Deane business empire was thriving.
In 1772, young Samuel Webb’s adventures began. At age nineteen he was dispatched to the Caribbean on the first of several highly successful voyages as the “factor” (business agent) for the family’s international trading business. While traveling, Webb began a life-long habit of writing engaging, informative letters to his family and friends. As he departed for the Caribbean he sent the first letter of his life-long correspondence to his sisters, which read in part:
New London, CT
Dec. 13, 1772
My ever dear sisters:
Is it possible? Can it be that I am to leave my native shore? That I am not to see, nor hear from you this winter ….
It is now almost a week since I have been here with my horses on board (for trading), ready to put to sea. But, the winds have been contrary, and the old seamen have not liked the looks of the weather. This evening the wind shifted to Northwest and no doubt we shall put to sea in the morning. Three or four days of sickness is what I expect when I first go out; happy shall I think myself if no other sickness attends me than seasickness.
At present I feel in a pensive, melancholy mood …. I am now going to amuse myself by going for a walk.
(PS) Dear Sisters it is not half an hours since I wrote. My Captain calls, “Fair Wind,” and we must sail immediately. This I write on board my vessel, the schooner Dolphin Captain Samuel Crowel Commander.
Adieu my sisters. May heaven bless and preserve you; (so) prays your affectionate brother Sam’l
On his first ocean venture, Webb was responsible for trading Connecticut horses, onions, lumber, and barrel staves for Caribbean sugar, molasses, and rum. Upon arriving in Jamaica he found the market price for horses was particularly low because of a recent surge in imports. Despite that annoyance, he was able to sell his entire cargo at a small profit. Following that initial success, he was soon dispatched again and again with unusually good results. By 1774 he was the “chief factor” for a pair of trading ships financed by his older brother, Joseph Webb III, Silas Deane, and other Connecticut investors.
In the spring of 1774 Webb began a brief but brilliant political career, as an assistant to his step-father, Silas Deane, an elected representative of the Connecticut state legislature. In Hartford, Deane emerged as a leader of the fight for colonial rights, serving on the key committees of “Correspondence” and of “Safety,” the two bodies chosen to coordinate the responses of the thirteen colonies to British “outrages” in America. Later that summer, Deane was elected to represent Connecticut at the First Continental Congress. In the fall, Deane took Webb with him to Philadelphia as his assistant, charging him with keeping notes, writing letters, and sending reports to their supporters at home. From Philadelphia Webb wrote to his older brother:
September 1, 1774
Dear Brother: … Yesterday we dined with Ye Congress to a number of about 400; enclosed you have the toasts to which we drank ….
Mr. (Paul) Revere got here yesterday express from Boston [bringing the Suffolk Massachusetts Resolves to boycott British imports] and I am in utmost haste …. Your affectionate brother SBW
Deane was a passionate advocate for a political break with England, and was again appointed to key committees. The committees of “Trade” and “Safety” were charged with planning and equipping the nation for an armed conflict with England. As Deane’s assistant, Samuel Webb became keenly aware of the issues separating the colonies from the mother country, and of the plans and the problems of arming a militia for the rebellion. With Deane’s assistance, Webb met with many of the leaders of the incipient revolution, including George Washington, Benjamin Franklin, Robert Morris, John Sullivan, etc.
In the spring of 1775 when news of the fighting at Lexington and Concord reached Wethersfield, Webb paid a visit to the captain of the local militia company, John Chester. Chester and Webb were good friends and “kin,” a year earlier Chester had married Webb’s youngest sister, Abigail. Both men knew that Barnabas Deane, the militia company ensign (most junior officer) was not eager to race off to war. Barnabas Deane and his brother Silas had big expansion plans for their shipping, trading, and merchandising empire. A quick decision was made within the family, probably over a round of rum in a local pub; Barnabas Deane resigned his commission and Webb became the new ensign of the Wethersfield Militia Company.
Thus, in April 1775, Ens. Samuel Webb marched off to Boston with the Wethersfield Militia, Silas Deane returned to the Congress in Philadelphia, and Barnabas Deane and Joseph Webb remained at home to manage the booming family businesses.
With the call to arms in April 1775, the Wethersfield Militia Company mustered on the village green and then marched off, 130-men strong, down the old “King’s Road,” soon to be renamed the Boston Post Road. Within a week some 20,000 militiamen from all over New England converged on Boston creating a disorganized, rag-tag, brawling, filthy tent city reaching along the harbor shore from Roxbury to Charleston. For the young, ill-disciplined, hordes of American militiamen it was a grand gathering at first; and then the weather changed. In early May heavy rains turned the camps into quagmires of mud. Hastily dug privies overflowed, tents sagged, and tempers flared. Rum flowed, brawls erupted, and the provisions ran out.
This was not an organized army, rather a collection of fiercely independent militia with none of the organization, training, and discipline necessary to forge, feed, and maintain a standing army. Upon arrival, and after witnessing the chaos in the camps, Captain Chester generously offered to release some of the older men who were most needed at home by their families and businesses. All of the officers and NCO’s and about ninety of the enlisted men remained with Captain Chester and Ensign Webb outside Boston until the end of the year. The Wethersfield Company would be one of the most impressive and well-documented of the militia companies in the camps surrounding Boston during the year-long siege.  They were the only militia company wearing uniforms, bright blue coats with red facings. Because of their impressive military attire and the exuberance of their youthful leadership, the Wethersfield men drew some very visible assignments during the year-long Siege of Boston.
Chester’s company was chosen to be the official guards for the area commander, Gen. Artemis Ward (until Washington arrived); as such they were provided with prime quarters in Christ’s Anglican Church in Cambridge near the general’s headquarters. Being Anglican Catholic (Church of England) the building was largely unused at the time and available as a militia barracks. The congregation consisted mostly of Tories, loyal to the Crown, thus hated by their neighbors. The parishioners had abandoned their homes, businesses, and their church to seek safety with the British Army in Boston. In Cambridge, Captain Chester’s company was regularly mustered in their impressive uniforms and marched off to provide guards for formal ceremonies such as prisoner-of-war exchanges, courts martial, hangings, and the general’s personal guards.
In June 1775 the Wethersfield Militia Company was deeply engaged in the first big fight of the war, the Battle of Bunker Hill. Two days after that clash, Captain Chester began a letter to his brother-in-law Joseph Webb describing the battle. Before he could complete his letter he was called away, leaving Samuel Webb to complete the tale to his brother. Part of it read:
Cambridge, MA April 18, 1775
My Dear brother: The horrors and devastations of war now begin to appear with us in earnest …. Last Friday afternoon orders were issued for about 1,800 of the province [Massachusetts} men and 200 of Connecticut men [including about 30 from Capt. Chester’s Company] to parade themselves at 6 o’clock … and there receive their orders. Near 9 o’clock they marched… and went to entrenching on Bunker’s Hill. Here they worked… and had a very fine fortification which the enemy never knew until morn. They then began a most heavy fire from the Cop’s Hill [in Boston] and from all the ships that could play….
About one o’clock PM we that were at Cambridge heard that the regulars were landing from their floating batteries and the alarm was sounded & we [were] ordered to march directly down to the Fort at Charlestown. Before our company could possibly get there the battle had begun in earnest, and cannon and musket balls were flying about our ears like hail … a hotter fire you can have not idea of…. Our men were in fine spirits. Your brother [Samuel Webb] and I led them and they kept their order very finely 2 & 2.
[At this point Samuel Webb takes over.] … Captain Chester is called off and begs me to go on with this letter. … On our march down we met many of our worthy friends wounded sweltering in their blood … We pushed on, and came in to the field of Battle. Through the cannonading of the ships, bombs, chain shot, ring shot & double headed shot flew as thick as hail, but thank Heaven few of our men suffered.
We mounted the summit [Bunker Hill]… and descended the hill into the field of battle, and began our fire very briskly. The regulars [British] fell in great plenty … but they keep a good front and stood their ground nobly. … Twice before [we arrived} they gave away – but [it was] not long before we saw numbers mounting the Walls of our fort [on Breed’s Hill]…. Our men on the fort were ordered to fire and make a swift retreat. We covered their retreat until they came up with us. Dead and wounded lay on every side of me – their groans were piercing indeed…
[Shamefully,] very few of our reinforcements came onto the field. Our orders then came to make the best retreat we could. We ran very fast up the hill [Bunker Hill]… and over Charleston Neck through the thickest of the ships fire. We rallied on another hill [Prospect Hill] and waited for them to come after us. … Here we were determined to die or conquer if they ventured over the neck. … They kept up a constant fire from ships and floating batteries all night. … How dismal was the sight to see the beautiful and valuable town of Charlestown all in flames.
… In this bloody engagement, we have lost 4 dead [all named] and 4 wounded [all named] …. The King’s troop to the number of 2 or 3,000 are now encamped on [Bunker Hill] ….
Chester and Webb and their courageous rear-guard actions were written up in countless letters and newspapers describing the battle; and a great many senior officers began to pay attention to their careers. Within a year Captain Chester was a colonel in command of a regiment of Connecticut militia, and in 1776 his regiment served with distinction at the battles of Long Island, White Plains, and the great victories at Trenton and Princeton.
Ensign Webb’s rise was equally meteoric but within the Continental Army. Within a month of Bunker Hill, Webb was promoted to the rank of captain, temporary major, and aide-de-camp (ADC) to Maj. Gen. Israel Putnam. Webb spent the next twelve months assisting “Old Put,” writing most of his letters and reports, a contribution greatly appreciated by General Washington as Putnam was not a paperwork man; his handwriting and his compositions were virtually incomprehensible.
Following the fight at Bunker Hill, the Siege of Boston dragged on for another year. Finally in March of 1776, the Americans positioned heavy cannons on Roxbury Heights overlooking the city. Faced with a potentially disastrous bombardment, the British commander in Boston ordered an evacuation of the garrison. General Washington briefly occupied Boston but soon marched his army south, anticipating that the British would return with a much larger force and that their target would be the more vulnerable port city of New York.
Meanwhile in the summer of 1775, Silas Deane was elected to the Second Continental Congress where he resumed his work on the Committees of Trade and Safety, and he was appointed Chairman of the first Congressional Naval Committee. Thus in his various committee posts, Deane was responsible for the offshore purchase of military weapons and supplies, the transport of those critical materials through the British blockade, and the building of an American Navy.
By the fall of 1775 the Webb and Deane family enterprises were laying the keels of a new line of sailing ships, blockade running sloops and privateers. Privateers were privately owned ships armed with cannons that were given state charters to roam the oceans and seize the cargoes of unarmed enemy merchant vessels. The “loot” would be divided among the owners, sailors, and the particular legislature providing the charter. The business could be a highly profitable, if the lightly-armed privateer avoided all confrontations with the potent warships of the British Navy.
Family letters reveal that the Webb and Deane family invested in several highly successful privateers, including the Revenge, Beaver, Washington, and Gates. According to the local town history the Revenge was built in Wethersfield. She carried a crew of sixty-four men and a battery of eight cannons. The Washington and the Gates were smaller ships of unknown size and armament. We know that all three ships worked together in at least one instance.  In a letter written in July of 1779 Webb reported to his brother-in-law Joseph Barrell (sister Sarah’s second husband) about their investments in privateering.
Providence RI. July 6, 1779
I congratulate you on the arrival of a large and valuable prize ship, laden with provisions and goods at New London. It was taken, ‘tis said, by the Revenge and two little Privateers, the Washington and the Gates. This I think will more than clear the first cost of our shares; and I wish they may be further successful …
Your affectionate brother, Sam’l B Webb
In 1776 Silas Deane lost his election bid to return to the Third Continental Congress. However, because of his knowledge of international trade and his Congressional experience he was dispatched to Paris by Congress in March 1776 as the first American diplomat charged with negotiating the purchase of weapons from the Europeans. He was soon joined by two Congressmen, Benjamin Franklin and Arthur Lee. By June 1, 1777 the three able Americans had dispatched some ten supply ships which successfully eluded the British Navy and deposited more than two thousand tons of muskets, swords, cannons, gunpowder, and miscellaneous military supplies.  In early 1777 some 22,000 French muskets and tons of gunpowder arrived in time to help arm the Americans confronting a British invasion army from Canada in the fall of 1777. Colonel Webb’s men would be among the first of the Continental Regiments armed with the new French muskets.
Meanwhile, the year 1776 was a disaster for General Washington and the Continental Army. In the spring Washington moved his men south from Boston and put them to work in New York, building a host of fortifications along the shorelines and bays of Manhattan, Long Island, Staten Island, and up the Hudson River. He soon found himself buried in mountains of logistical, operational, and administrative problems and paperwork. Congress generously provided him with an Army but no staff for handling plans, orders, reports, correspondence, purchase orders, etc. To create the equivalent of a modern general staff, Washington began collecting a cadre of Aides-de-Camp (ADC), “young gentlemen of ability and confidentiality” who functioned as his administrative assistants. He frequently called them his “pen men.”
One of the first men he approached to be an ADC was a young, bright, hard-working, experienced political and military aide, and a proven combat leader, Maj. Samuel B. Webb. In June of 1776, Washington promoted Webb to the rank of lieutenant colonel and ADC on his staff. For the next six months, Webb spent endless hours writing the general’s letters, orders, and reports, carrying his messages, debating tactics with him, and providing him with moral support. Webb worked directly with Washington during the disastrous summer and fall campaigns of 1776, an endless series of defeats in which the Continental Army was pushed out of New York City and all the way across New Jersey. Throughout that difficult time, Webb was far more than just a “pen man”; he was an active and aggressive battlefield assistant, the only aide on Washington’s staff who was wounded three times in battle during the first two years of the war. Webb was struck by musket balls at the battles of Bunker Hill, White Plains, and Trenton. On the frozen, snowy night of December 25-26, 1776, Webb crossed the Delaware River in the same boat as General Washington. Later that day he was shot off his horse while carrying orders across the battlefield from his boss to General Sullivan.
A month later (January 1777), while recuperating at home, Webb was promoted by Washington to the rank of regimental colonel with orders to recruit an “additional” Connecticut Regiment of the Continental Army. In December, 1777, Colonel Webb was captured by a British warship while leading a hazardous, winter assault across Long Island Sound in small boats. As was the custom of the day, officers taken prisoner were treated well, while enlisted captives were treated abominably. Colonel Webb was released on his own recognizance to board in a private home on Long Island. During his captivity he traveled frequently and extensively between enemy lines on “personal business.” His notes confirm that he made several trips to his home and family in Wethersfield, his regiment in Rhode Island, General Washington’s headquarters, and to woo and win the heart of an attractive young lady in New Jersey.
Surprisingly for a prisoner of the British, Webb also continued to dabble in the business of privateering, exchanging correspondence with his family on the subject. In a letter from Joseph Barrell, the first husband of his sister Sarah, Webb received the happy news that their privateers Gates and Beaver had seized a cargo of some seventy hogsheads of high proof Jamaican rum. Barrell also suggested that Webb might want to “sing small” (say little) about his privateering ventures while he was still a prisoner of the British. Their letters might be intercepted by Webb’s captors who might decide to delay Webb’s release from captivity.
Boston 12 August 1779
My dear brother: … I am rejoiced you have a fair prospect of a (prisoner) exchange….
The prizes sent in by the (privateers) Gates and Beaver are very clever… 70 odd hogsheads of high proof Jamaica (rum) are better than 20 kicks in the britches; nay I prefer it to 50.
I think you had best sing small about this until your exchange is complete ….
Possibly it was the handsome returns from his privateering ventures that helped convince Webb that it was time to get married. In the summer of 1780 while still a prisoner of war, Samuel B. Webb wooed and won the heart of a young, New Jersey maiden, Miss Elizabeth Bancker of North Raritan. They married quietly in a small ceremony, hoping to avoid the attention of local Tories, on October 22, 1780. Their honeymoon was brief as Webb was released four months later in a prisoner exchange and he returned immediately to his regiment.
A few months later, in May 1781, Webb travelled to Wethersfield, Connecticut to his childhood family home, now the residence of his older brother Joseph, where General Washington and French General Rochambeau were meeting to plan the final major conflict of the American Revolution, the siege of Yorktown. Afterwards, Webb returned to West Point where his regiment remained on garrison duty until it was disbanded in September 1783. Upon his retirement, in recognition of his war-time services, he was promoted brigadier general by General Washington. He remained a personal friend of Washington, helping to found the Society of Cincinnatus, a fraternal veterans’ organization of army officers, and serving as grand marshal at Washington’s inauguration in 1789.
There is a curious twist to the ending of this story. In the summer of 1786 a personal dispute arose between General Webb and his former second in command, Lt. Col. William Smith Livingston. The exact details of that disagreement are not known, but from their correspondence it appears that Webb felt Livingston had betrayed him.  Webb believed that Livingston had suppressed evidence, in the form of a personal letter, which exonerated Webb from rumors circulating implicating Webb in potentially criminal activities. Offended that his old comrade had failed to support him, Webb asked for the “satisfaction” of a pistol duel.
Col. Samuel B. Webb and his former adjutant Lt. Col. William Smith Livingston met at Paulus Hook, New Jersey to resolve their insoluble differences. At dawn on September 5, 1786 the two gentlemen paced off their agreed distance, turned, aimed, and Webb fired. He missed. Livingston then spoke: “you have missed me. I came here to answer demands you had against me – had you suppressed that letter, which I never said you had, your life would be recompense I cannot ask – I shall discharge my pistol in the air” The two gentlemen, former comrades in arms, shook hands and the misunderstanding seems to have passed.
Colonel Webb’s duel has been long forgotten. Fortunately, his home, his church, his life-story and that of his neighbors, and their contributions to the Revolution have been lovingly honored and preserved by his admirers and his hometown of Wethersfield, Connecticut.
 For a biography of Webb see: Worthington Chauncey Ford (Ed.), Correspondence and Journals of Samuel Blachley Webb (Wickersham: NY, 1893), 3:249-396.
 J. Watson Webb, Reminiscences of General Samuel B. Webb (New York: Globe, 1882), 33.
 The homes of Joseph Webb and Silas Deane in Wethersfield, Connecticut, are National Historic Landmarks. They have been completely restored and furnished and are open to the public.
 George L. Clark, Silas Deane: A Connecticut leader in the American Revolution (New York: Putnam, 1913), 3, 4.
 Ford, Correspondence, 1:5-8, 15-17, 38, 40-43.
 Paul Lockhart, The whites of their eyes: Bunker Hill, the first American Army, and the emergence of George Washington (New York: Harper, 2011), 39-41, 79-80, & 176.
 Ford, Correspondence, 1:87. See also Lockhart, Bunker Hill, 176-77.
 Ford, Correspondence, 1:63-69 & 73-82. This letter is condensed for clarity.
 George L. Clark, Silas Deane: A Connecticut leader in the American Revolution (New York: Putnam, 1913), 3,4.
 Henry R. Stiles and Sherman W. Adams, The History of ancient Wethersfield, Connecticut Vol. 1 Part 2 (New York: Grafton Press, 1904), 497- 503.
 Ibid., 498.
 Ford, Correspondence, 2:176.
 Charles Rappleye, Robert Morris: Financier of the American Revolution (New York: Simon & Schuster. 2010), 101-2. See also John Ferling, Almost a miracle: The American victory in the War of Independence (Oxford: Oxford University Press, 2007), 564.
 Arthur S. Lefkowitz, George Washington’s indispensable men: the 32 Aides-de-Camp who helped win American independence (Mechanicsburg, PA: Stackpole, 2003), xv – xvii, 53-55.
 Ford, Correspondence, 3:64-66.