University of Virginia Library

CHAPTER XIV

RICHARD HENDERSON AND THE
TRANSYLVANIA COMPANY

EARLY in 1774, chastened by his own disastrous
failure the preceding autumn,
Boone advised Judge Henderson that the time
was auspicious for opening negotiations with
the Cherokees for purchasing the trans-Alleghany
region.[1] In organizing a company for
this purpose, Henderson chose men of action
and resource, leaders in the colony, ready for
any hazard of life and fortune in this gigantic
scheme of colonization and promotion. The
new men included, in addition to the partners
in the organization known as Richard Henderson

and Company, were Colonel John Luttrell,
destined to win laurels in the Revolution,
and William Johnston, a native of Scotland,
the leading merchant of Hillsborough.[2]

Meeting in Hillsborough on August 27,
1774, these men organized the new company
under the name of the Louisa Company. In
the articles then drawn up they agreed to "rent
or purchase" a tract of land from the Indian
owners of the soil for the express purpose of
"settling the country." Each partner obligated
himself to "furnish his Quota of Expenses
necessary towards procuring the grant."
In full anticipation of the grave dangers to
be encountered, they solemnly bound themselves,
as "equal sharers in the property," to
"support each other with our lives and fortunes."[3]
Negotiations with the Indians were
begun at once. Accompanied by Colonel Nathaniel
Hart and guided by the experienced
Indian-trader, Thomas Price, Judge Henderson
visited the Cherokee chieftains at the Otari
towns. After elaborate consultations, the latter
deputed the old chieftain, Atta-kulla-kulla,

a young buck, and a squaw, "to attend the
said Henderson and Hart to North Carolina,
and there examine the Goods and Merchandize
which had been by them offered as the Consideration
of the purchase." The goods purchased
at Cross Creek (now Fayetteville,
North Carolina), in which the Louisa Company
"had embarked a large amount," met the
entire approval of the Indians—the squaw in
particular shrewdly examining the goods in
the interest of the women of the tribe.[4]

On January 6, 1775, the company was again
enlarged, and given the name of the Transylvania
Company—the three new partners being
David Hart, brother to Thomas and Nathaniel,
Leonard Henley Bullock, a prominent
citizen of Granville, and James Hogg, of
Hillsborough, a native Scotchman and one of
the most influential men in the colony. In the
elaborate agreement drawn up reference is explicitly
made to the contingency of "settling
and voting as a proprietor and giving Rules
and Regulations for the Inhabitants etc."[5]
Hillsborough was the actual starting-point for

the westward movement, the first emigrants
traveling thence to the Sycamore Shoals of the
Watauga. In speaking of the departure of
the settlers, the first movement of extended and
permanent westward migration, an eye-witness
quaintly says: "At this place [Hillsborough]
I saw the first party of emigrant families that
moved to Kentucky under the auspices of
Judge Henderson. They marched out of the
town with considerable solemnity, and to many
their destination seemed as remote as if it had
been to the South Sea Islands."[6]

Meanwhile, the "Proposals for the encouragement
of settling the lands etc.," issued on
Christmas Day, 1774, were quickly spread
broadcast through the colony and along the
border.[7] It was the greatest sensation North
Carolina had known since Alamance; and
Archibald Neilson, deputy-auditor and naval
officer of the colony, inquired with quizzical
anxiety: "Pray, is Dick Henderson out of
his head?" The most liberal terms, proffered
by one quite in possession of his head, were
embodied in these proposals. Land at twenty

shillings per hundred acres was offered to
each emigrant settling within the territory
and raising a crop of corn before September
1, 1775, the emigrant being permitted to take
up as much as five hundred acres for himself
and two hundred and fifty acres for each
tithable person under him. In these "Proposals"
there was no indication that the low
terms at which the lands were offered would
be maintained after September 1, 1775.[8] In
a letter to Governor Dunmore (January,
1775), Colonel William Preston, county surveyor
of Fincastle County, Virginia, says:
"The low price he [Henderson] proposes to
sell at, together with some further encouragement
he offers, will I am apprehensive induce
a great many families to remove from this
County (Fincastle) & Carolina and settle
there."[9] Joseph Martin, states his son, "was
appointed entry-Taker and agent for the Powell
Valley portion" of the Transylvania Purchase
on January 20, 1775; and "he (Joseph
Martin) and others went on in the early part
of the year 1775 and made their stand at the

ADVERTISEMENT OF THE TRANSYLVANIA COMPANY

From The Virginia Gazette, September 30, 1775

very spot where he had made corn several years
before."[10] In speaking of the startling design,
unmasked by Henderson, of establishing
an independent government, Colonel Preston
writes to George Washington of the contemplated
"large Purchase by one Col.o Henderson
of North Carolina from the Cherokees.
. . . I hear that Henderson talks with great
Freedom & Indecency of the Governor of Virginia,
sets the Government at Defiance & says
if he once had five hundred good Fellows settled
in that Country he would not Value Virginia."[11]

Early in 1775 runners were sent off to the
Cherokee towns to summon the Indians to the
treaty ground at the Sycamore Shoals of the
Watauga; and Boone, after his return from a
hunt in Kentucky in January, was summoned
by Judge Henderson to aid in the negotiations
preliminary to the actual treaty. The
dominating figure in the remarkable assemblage
at the treaty ground, consisting of
twelve hundred Indians and several hundred
whites, was Richard Henderson, "comely in

person, of a benign and social disposition,"
with countenance betokening the man of strenuous
action—"noble forehead, prominent nose,
projecting chin, firm-set jaw, with kindness
and openness of expression." Gathered about
him, picturesque in garb and striking in appearance,
were many of the buckskin-clad leaders
of the border—James Robertson, John
Sevier, Isaac Shelby, William Bailey Smith,
and their compeers—as well as his Carolina
friends John Williams, Thomas and Nathaniel
Hart, Nathaniel Henderson, Jesse Benton,[12]
and Valentine Searcy.

Little was accomplished on the first day of
the treaty (March 14th); but on the next day,
the Cherokees offered to sell the section bargained
for by Donelson acting as agent
for Virginia in 1771. Although the Indians
pointed out that Virginia had never paid the
promised compensation of five hundred pounds
and had therefore forfeited her rights, Henderson
flatly refused to entertain the idea of
purchasing territory to which Virginia had the
prior claim. Angered by Henderson's refusal,

The Dragging Canoe, leaping into the circle of
the seated savages, made an impassioned speech
touched with the romantic imagination peculiar
to the American Indian. With pathetic eloquence
he dwelt upon the insatiable land-greed
of the white men, and predicted the extinction
of his race if they committed the insensate
folly of selling their beloved hunting-grounds.
Roused to a high pitch of oratorical fervor,
the savage with uplifted arm fiercely exhorted
his people to resist further encroachments at
all hazards—and left the treaty ground. This
incident brought the conference to a startling
and abrupt conclusion. On the following day,
however, the savages proved more tractable,
agreeing to sell the land as far south as the
Cumberland River. In order to secure the
additional territory watered by the tributaries
of the Cumberland, Henderson agreed to pay
an additional sum of two thousand pounds.
Upon this day there originated the ominous
phrase descriptive of Kentucky when The
Dragging Canoe, dramatically pointing toward
the west, declared that a Dark Cloud
hung over that land, which was known as the
Bloody Ground.

On the last day, March 17th, the negotiations
were opened with the signing of the
"Great Grant." The area purchased, some
twenty millions of acres, included almost all the
present state of Kentucky, and an immense
tract in Tennessee, comprising all the territory
watered by the Cumberland River and all its
tributaries. For "two thousand weight of
leather in goods" Henderson purchased "the
lands lying down Holston and between the
Watauga lease, Colonel Donelson's line and
Powell's Mountain" as a pathway to Kentucky
—the deed for which was known as the "Path
Deed." By special arrangement, Carter's
Valley in this tract went to Carter and Lucas;
two days later, for two thousand pounds,
Charles Robertson on behalf of the Watauga
Association purchased a large tract in the valleys
of the Holston, Watauga, and New Rivers;
and eight days later Jacob Brown purchased
two large areas, including the Nolichucky
Valley. (Compare map.) This historic

treaty, which heralds the opening of the
West, was conducted with absolute justice and
fairness by Judge Henderson and his associates.
No liquor was permitted at the treaty
ground; and Thomas Price, the ablest of the
Cherokee traders, deposed that "he at that time
understood the Cherokee language, so as to
comprehend everything which was said and to
know that what was observed on either side was
fairly and truly translated; that the Cherokees
perfectly understood, what Lands were the
subject of the Treaty. . . ." The amount
paid by the Transylvania Company for the imperial
domain was ten thousand pounds sterling,
in money and in goods.[13]

Although Daniel Boone doubtless assisted
in the proceedings prior to the negotiation of
the treaty, his name nowhere appears in the
voluminous records of the conference. Indeed,
he was not then present; for a fortnight
before the conclusion of the treaty he was commissioned
by Judge Henderson to form a
party of competent woodmen to blaze a passage
through the wilderness. On March 10th

this party of thirty ax-men, under the leadership
of Boone, started from the rendezvous,
the Long Island of Holston, to engage in the
arduous labor of cutting out the Transylvania
Trail.[14]

Henderson, the empire-builder, now faced
with courage and resolution the hazardous task
of occupying the purchased territory and establishing
an independent government. No mere
financial promoter of a vast speculative enterprise,
he was one of the heroic figures of the
Old Southwest; and it was his dauntless courage,
his unwavering resolve to go forward in
the face of all dangers, which carried through
the armed "trek" to a successful conclusion.
At Martin's Station, where Henderson and
his party tarried to build a house in which to
store their wagons, as the road could be cleared
no further, they were joined by another party,
of five adventurers from Prince William
County, Virginia.[15] In Henderson's party
were some forty men and boys, with forty pack-horses
and a small amount of powder, lead,

FIRST PAGE OF RICHARD HENDERSON'S DIARY

From the original owned by the Wisconsin State Historical Society

salt, and garden-seeds. The warning freely
given by Joseph Martin of the perils of the
path was soon confirmed, as appears from the
following entry in Henderson's diary:

The following historic letter, which reveals
alike the dogged resolution of Boone and his
reliance upon Henderson and his company in
this black hour of disaster, addressed "Colonel
Richard Henderson—these with care," is eloquent
in its simplicity:

This dread intelligence caused the hearts of
strong men to quail and induced some to turn
back, but Henderson, the jurist-pioneer, was
made of sterner stuff. At once (April 8th) he
despatched an urgent letter in hot haste to the
proprietors of Transylvania, enclosing Boone's
letter, informing them of Boone's plight and
urging them to send him immediately a large
quantity of powder and lead, as he had been
compelled to abandon his supply of saltpeter
at Martin's Station. "We are all in high spirits,"
he assures the proprietors, "and on thorns
to fly to Boone's assistance, and join him in
defense of so fine and valuable a country."
Laconically eloquent is this simple entry in
his diary: "Saturday the 8th. Started abt. 10
oClock Crossed Cumberland Gap about 4
miles met about 40 persons Returning from
the Cantucky, on Acct. of the Late Murders
by the Indians could prevail on one only to

return. Memo Several Virginians who were
with us return'd."

There is no more crucial moment in early
Western history than this, in which we see the
towering form of Henderson, clad in the picturesque
garb of the pioneer, with outstretched
arm resolutely pointing forward to the "dark
and bloody ground," and in impassioned but
futile eloquence pleading with the pale and
panic-stricken fugitives to turn about, to join
his company, and to face once more the mortal
dangers of pioneer conquest. Significant indeed
are the lines:

The spirit of the pioneer knight-errant inspires
Henderson's words: "In this situation, some
few, of genuine courage and undaunted resolution,
served to inspire the rest; by the help
of whose example, assisted by a little pride and
some ostentation, we made a shift to march
on with all the appearance of gallantry, and,

cavalier like, treated every insinuation of danger
with the utmost contempt."

Fearing that Boone, who did not even know
that Henderson's cavalcade was on the road,
would be unable to hold out, Henderson realized
the imperative necessity for sending him
a message of encouragement. The bold
young Virginian, William Cocke, volunteered
to brave alone the dangers of the murderhaunted
trail—to undertake a ride more truly
memorable and hazardous than that of Revere.
"This offer, extraordinary as it was, we could
by no means refuse," remarks Henderson, who
shed tears of gratitude as he proffered his sincere
thanks and wrung the brave messenger's
hand. Equipped with "a good Queen Anne's
musket, plenty of ammunition, a tomahawk,
a large cuttoe knife [French, couteau], a
Dutch blanket, and no small quantity of jerked
beef," Cocke on April 10th rode off "to the
Cantuckey to Inform Capt Boone that we were
on the road." The fearful apprehensions felt
for Cocke's safety were later relieved, when
along the road were discovered his letters informing

Henderson of his arrival and of his
having been joined on the way by Page Portwood
of Rowan. On his arrival at Otter
Creek, Cocke found Boone and his men, and
on relating his adventures, "came in for his
share of applause." Boone at once despatched
the master woodman, Michael Stoner, with
pack-horses to assist Henderson's party, which
he met on April 18th at their encampment "in
the Eye of the Rich Land." Along with "Excellent
Beef in plenty," Stoner brought the
story of Boone's determined stand and an account
of the erection of a rude little fortification
which they had hurriedly thrown up to
resist attack. With laconic significance Henderson
pays the following tribute to Boone
which deserves to be perpetuated in national
annals: "It was owing to Boone's confidence
in us, and the people's in him, that a stand
was ever attempted in order to wait for our
coming."

In the course of their journey over the
mountains and through the wilderness, the
pioneers forgot the trials of the trail in the

face of the surpassing beauties of the country.
The Cumberlands were covered with rich undergrowth
of the red and white rhododendron,
the delicate laurel, the mountain ivy, the flameazalea,
the spicewood, and the cane; while the
white stars of the dogwood and the carmine
blossoms of the red-bud, strewn across the
verdant background of the forest, gleamed in
the eager air of spring. "To enter uppon a
detail of the Beuty & Goodness of our Country,"
writes Nathaniel Henderson, "would be
a task too arduous. . . . Let it suffice to tell
you it far exceeds any country I ever saw or
herd off. I am conscious its out of the power
of any man to make you clearly sensible of
the great Beuty and Richness of Kentucky."
Young Felix Walker, endowed with more
vivid powers of description, says with a touch
of native eloquence:

On the journey Henderson was joined in
Powell's Valley by Benjamin Logan, afterward
so famous in Kentucky annals, and a
companion, William Galaspy. At the Crab
Orchard they left Henderson's party; and
turning their course westward finally pitched
camp in the present Lincoln County, where

Logan subsequently built a fort. On Sunday,
April 16th, on Scaggs's Creek, Henderson
records: "About 12 oClock Met James McAfee
with 18 other persons Returning from
Cantucky." They advised Henderson of the
"troublesomeness and danger" of the Indians,
says Robert McAfee junior: "but Henderson
assured them that he had purchased the whole
country from the Indians, that it belonged to
him, and he had named it Transylvania. . . .
Robt, Samuel, and William McAfee and 3
others were inclined to return, but James opposed
it, alleging that Henderson had no right
to the land, and that Virginia had previously
bought it. The former (6) returned with
Henderson to Boonesborough." Among those
who had joined Henderson's party was Abraham
Hanks from Virginia, the maternal grandfather
of Abraham Lincoln; but alarmed by
the stories brought by Stewart and his party
of fugitives, Hanks and Drake, as recorded
by William Calk on that day (April 13th),
turned back.[19]

At last the founder of Kentucky with his

little band reached the destined goal of their
arduous journeyings. Henderson's record on
his birthday runs: "Thursday the 20th
[April] Arrived at Fort Boone on the
Mouth of Oter Creek Cantuckey River where
we were Saluted by a running fire of about
25 Guns; all that was then at Fort. . . . The
men appeared in high spirits & much rejoiced
in our arrival." It is a coincidence of historic
interest that just one day after the embattled
farmers at Lexington and Concord
"fired the shots heard round the world," the
echoing shots of Boone and his sturdy backwoodsmen
rang out to announce the arrival of
the proprietor of Transylvania and the birth
of the American West.