Origins of Jennings’ Peregrinations:

                      The Infamous Jennings Brothers of Early Colonial America


Nicholas E. Hollis


One of the more intriguing and endearing features of tracing the lives of long departed family ancestors are the real time visits to areas they once inhabited,  traveling along routes of their migrations and revisiting their histories at museums, historical societies and libraries. This past summer, as a descendant of one of America’s oldest colonial families, I had such an opportunity while visiting the Hamptons on Long Island . I was not there to hob knob with the elite and famous- or to linger on the beaches but rather to gather information on one my family’s early settlers- John Jennings of Southampton (1617-1686)—whose life forms a study in contrasts perplexing many genealogists and family historians over more than three centuries.


Records from the Connecticut Colony at Hartford reveal John Jennings arrived in the New World in 1635 with his father (also named John) and a brother, Joshua . His older brother, Nicholas, had immigrated from England a year earlier on the “Francis” which had sailed from Ipswich and landed at Agawan on the Connecticut River. Nicholas later gained property at Hartford for his service in the Pequot Wars (1636-39). . Shortly after their father died around 1641, the brothers’ lives began unraveling. From a similarity of their behavior patterns, all three appear to have been non-conformist, headstrong rebels and the puritanical nature of the colony authority inspired run-ins with elders. This resulted in a series of minor charges – from beating a cow, slander, and dereliction of guard duties – finally leading to a serious charge of “fornication” leveled at the older brother Nicholas and an indentured woman (Margaret), who later became his wife. The couple relocated to Old Saybrook.  In 1650, a Hartford court fined John Jennings heavily for resisting duties (presumably as some kind of indentured servant) and profanity- which resulted in his relocation to Old Saybrook- possibly to be near his more propertied brother Nicholas and his family.1/ The same year the Hartford court fined two friends of Joshua Jennings for assisting his escape from the “power of authority”. Joshua soon reappeared in Fairfield, Connecticut, settled down and began an illustrious legacy, with Mary Williams, who he had married several years before.


Across the sparkling waters of the Sound on the horizon stretched the fertile coast of Long Island- visible on a clear day. Its promise of new beginnings afforded John Jennings all the rationale he needed for a  relocation to Southampton – and his name appears on a list of inhabitants in 1657 settled in the hamlet of North Sea on the shore of Peconic Bay. North Sea had provided a safe haven for debarkation of the original Hampton settlers some years earlier and at the “Old Town” several miles to the south.


1/Evidence exists that Nicholas Jennings owned property in Old Lyme and Saybrook, but his tenuous hold on respectability was shattered in 1661 when he and his wife were accused/tried for witchcraft. Although acquitted. Nicholas/Margaret’s family was broken up. They were forced to sell property and their children were apprenticed


North Sea was the first significant extension of “Old Town” by 1650- two years after the permanent location at Southampton village was established on its present site. East Hampton had been settled in 1649, but was not an offshoot of Southampton. The actual founder of North Sea, occasionally referred to as “Faversham”, was John Ogden, who appears in the 1657 list of inhabitants.


North Sea initially flourished as a whaling port and its oil was shipped to New England, and possibly even to England itself- before other ports at Sagg and Hecox emerged as more convenient. All ports carried on lively trade with Boston and other New England ports as well as the West Indies- more than one hundred years before the emergence of New Bedford as the dominant whaling center. There was little commerce with New York (New Amsterdam) while it remained under Dutch influence, and even after England took control. Lord Cornbury, complaining to the House of Lords in 1703 stated that “Indeed the people of the East End of Long Island are not very willing to be persuaded that they belong to this province. They are full of New England principles. They choose rather to trade with the people of Boston, Connecticut and Rhode Island than with the people of New York”


Town records reveal in 1662 John Jennings purchased the homestead of John Oldfields. Two years later he made a brief contract with the Town of Easthampton as indicated by its town record (Vol. I, p. 176) where he was “granted liberty to dig a cellar to dwell in some convenient place near the school house which was to be built with the proviso that when he was finished with its use, the site would revert to the town – he having no interest therein except to procure an acceptable habitat” 2/


John Jennings reappears in 1666 linked with the North Sea settlement whaling list and later in 1672 Jennings was appointed as a customs collector with John Laughton due to “abuses in the landing of tobacco” – presumably duty-free- which became identified as a problem by Governor Richard Nicoll in 1668. Jennings also purchased (December 13) from the same John Laughton (for L50) the right of commonage at North Sea, reserving the right to pasture a calf or yearling on the little neck of land.


Almost four years earlier Jennings had accelerated his public social standing by petitioning his neighbors successfully to allow him the right to fence a meadow on the north side of the Nyack River as part of his property. If afterward when others divided their holdings and he had preempted too much –he agreed to relocate the fence. On April 20, 1670, John Jennings and others sold the property to John David for L50 of commonage in Southampton “not within the lyne of a hamlet commonly called and known as North Sea” Later, that same year Jennings served as an appraiser in the inventory of the estate of Thomas Sayre.


By the 1680s our Jennings subject was still buying and selling, largely divesting his real

Estate- and his will is probated in 1686 with five children named, including another John



2/ History of the Town of Southampton, James Truslow Adams, p.82

Lt. William, Joanna, Sarah and Samuel.  Jennings had shed his earlier image and

 became a pillar of the community. All his children remained at Southampton, and prospered with large families of their own. By the outbreak of the American Revolution no fewer than nine households in Southampton were headed by Jennings.3/


The two remaining subjects of this inquiry- both direct descendants of the first John Jennings of Southampton- demonstrate his youthful rebellious tendencies- as a family trait- did not lie dormant for long.


Refusing the “Loyalty Oath”


The example of Israel Jennings, a thirty year old farmer living near Southampton as the clouds of the Revolution gathered, is provided. British raiding parties had begun arriving to collect dairy and foodstuffs for General Howe’s British army besieged in Boston in late 1775. Farmers like Jennings were threatened with demands that included they swear allegiances to the Crown or suffer complete confiscation of all property.


Pressure mounted in 1776 as Howe deployed for his invasion of New York and used the Hamptons as a staging area with the British Navy while the main body mobilized in Nova Scotia. The Jennings family, known for its revolutionary zeal, had substantial property. Israel Jennings, great grandson of the original John, refused the oath and was forced to flee across to Connecticut where the family had an even stronger enclave at Fairfield along the “Revolutionary Road”. In July 1779, in reprisal for its reputation as a hotbed of patriotism, the British attacked and burned Fairfield, forcing Israel Jennings to gather his family (Charity Freeman and infant son, Israel) and begin a tortuous migration west. Eventually, he traveled down the Ohio to Maysville, Kentucky and later purchased property, settling in Brown county, Ohio east of Cincinnati in the small town of Georgetown. Israel turned his agrarian skills into a prosperous farm north of town and lived until 1830. It is likely he and his family did business with Jesse Grant, a local tanner, whose son, Ulysses often assisted with tending (and riding) the horses. Young Ulysses would later graduate from West Point, become the hero of the Union in the Civil War and 18th president of the United States. Israel’s son (also Israel) had also grown up, married (Mary Waters) and moved west near Salem, Illinois outside St. Louis. He too became a prosperous farmer, got elected to the State legislature and fathered a number of children, one of whom, Charles Waters Jennings, became the father of William Jennings Bryan’s mother (Mariah Elizabeth Jennings, 1834-1896). Israel lived to be ninety-six and is buried next to his son Charles (1802-1872) in a quiet cemetery east of Salem along old U.S. route 50. Their graves are only a stone’s throw from Mariah’s – the woman who birthed America’s greatest populist, William Jennings Bryan (1860-1925)- three time Democratic presidential nominee known for his silver tongued oratory and lifelong battle against the moneyed classes of Wall Street. One of Bryan’s cousins, William Sherman Jennings, (1863-1920)- also born at Salem- grew up to become a famous populist governor of Florida at the turn of the century. Jennings fought Henry Flagler and the railroad lobby and played an important role in the development of South Florida, while protecting the Everglades.


3/ History of Southampton, LI New York w/Genealogies, George Rogers Howell, p. 330

On the Revolutionary Road – Marching West


Another great grandson of John Jennings, Jacob, (1744-1813) begin life in Scotch Plains, New Jersey, became a physician in Hunterdon county. His father, and at least three other Jennings’ brothers (or cousins) had survived a shipwreck off Perth Amboy in 1726 by swimming to shore to begin their westward move from Long Island.


Dr. Jacob Jennings became a leading revolutionary, marched with General George Washington and was wounded at Trenton. He later became a minister in southwestern Pennsylvania near Uniontown. His offspring included several illustrious politicians, including Jonathan Jennings, Indiana’s first governor (1784-1834), Obadiah (1778-1832) a lawyer turned ordained minister, who later became Andrew Jackson’s preacher in Nashville, Tennessee and David Jennings (1787-1834), who became a U.S. Congressman from Belmont, Ohio. Another brother from this famous brood, Samuel Kennedy Jennings, became a surgeon and founder of the Washington Medical College in Baltimore, Maryland.


Chasing these ancestral wanderings in modern times – with high gas prices, and reduced library hours – can be frustrating, yet still inspirational . I would not trade my research travels along America’s byways, great rivers, parks and wonderful old towns forgotten in the freeway rush – for anything. With internet resources and the assistance of local historians and librarians, teasing the genealogical threads is much easier. On the downside, with old stones crumbling and private grave plots overgrown in brambles, even the symbolic (physical) markers of their pioneering lives, well-lived, are now often indecipherable and fading.


A few years ago I was invited to speak at a Memorial Day program dedicating a new monument to a forgotten farmer-soldier from the War of 1812 in central Kentucky (Lt. Colonel William Jennings, 1771-1831). En route I took a detour near Huntington, West Virginia, climbed into some bluffs and discovered a small family plot where William Jennings Bryan himself once placed carved stones honoring his paternal grandparents. Bryan knew the character value of appreciation to his ancestors and he had retraced their steps to a remote hilltop off U.S. Route 60. This discovery inspired me to revisit central Illinois under a boiling August sun to locate the grave of Israel Jennings- born in Southampton, Long Island and buried in Salem, Illinois—and thus confirm the link between my rebellious Jennings ancestors and the Great Commoner – Bryan. The thermostat reached over the century mark, but through the perspiration there was a feeling of triumph and exaltation. I was reminded of the old proverb:  To discover one’s ancestor is a marvelous thing.


                     “ Our ancestors, whether we know who they were or not, roll away

                           At gathering speed into the past, at times taking us with them

                           From our summit, turning back to look, we can see them fading

                           Into the distance, the perspective diminishing head by head,

                           Individuals merging into the crowd and beyond that into the misty

                      Ramifications of history- East of us, is a synthesis of his race”


                                                                                              (Sir Robert Stillwell)