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Authors: John Keene

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Pennyman, a widower and veteran, ran general provision shops in
Dorchester and Milton, the latter purchased at a sharp discount from a Loyalist
recently emigrated to Canada. A native of the Narraganset Plantations, he had earned
a reputation for probity in all matters financial, and rectitude in all matters
moral, and had acquired Zion both because of the low cost and because he required
the services of a slave of considerable strength who could read English and reckon
figures. The menagerie of Pennyman's home, the slave soon learned, was utterly
different from that of the Wantones'. Instead of sleeping in his master's small but
bearable attic, his quarters now consisted of a windowless, zinc-roofed shack, which
might once have been a toolshed, furnished only with a pallet bed and a rusted
chamberpot, several hundred yards away from the main edifice. His daily routine also
diverged markedly from that of his earlier life in Roxbury: for Pennyman expected
him to ride out with an assistant to one of his shops six days a week, and spend the
entire workday lifting, lading, packing, unpacking, registering and moving stock,
such as apparel of all sorts, furniture, books, kitchenware, provisions, yard and
garden tools, and farm and estate implements. There were no other Blacks, or even
Indians, in Pennyman's household; only his Irish maid, Nellie, a Welsh manservant,
James, and his assistants in the shops, all boys of English or Yankee heritage, none
of whom showed the least inclination towards socializing with a Negro. Unless the
situation demanded it, in fact, none of them, including Pennyman, spoke to him at
all.

Although Zion worked commendably at his new post for almost six months
(without even the smallest infraction beyond purloining several bottles of Malden
rum), the long rides, the isolation and lack of companionship, his continued
bondage, and the lure of the nearby ocean had begun to affect him perniciously. He
especially bridled at Pennyman's austerities: the provision of a minimum of food,
and no spices at all, at meals; a moratorium on singing or celebrations of any kind,
particularly during those hours that he set aside for his ledger books or to read
the Gospel; and the requirement of clothes of a plain nature especially on holy
days, for Pennyman had not been awakened by the preachings of Edwards or any other
deliverer great or small. One morning, after unloading cases of sugar, flour,
molasses, salt, suet, cranberry bread, sweet currants, and apples, and casks of rum,
French brandy, Boston beer, and Madeira wine, Zion began singing aloud one of the
songs he had learned from New Mary to pass the time, when he thought he overheard
one of the shop assistants noting how perverse it was that “music should arise from
a tarpit.” Confronting the man, who peppered him with epithets, Zion could no longer
restrain himself and flattened the man with one blow. A bullet, once fired, cannot
be recalled: Fearing the repercussions of his action, he fled on horse northward to
Boston, tinderbox of liberty. After abandoning his mount in the marshlands near
Boston Neck, he ran until he had reached the famed Beacon Hill portion of the
Tremountain. He concealed himself in a stand of box, waiting for the cover of
darkness before proceeding to the home of a cousin of Lacy who lived in Green
Street, near the Mill Pond. Here and at another safe house run by free blacks he
remained for several weeks, before shipping out without a permit from Hatch's Wharf
on a clipper bound for Nantucket.

The sea momentarily opened a new chapter in the book of Zion's life. He
sailed on a Kittery-based sloop, the
Hazard
, which ventured as far south as
the English Caribbean, and on which he experienced the freedoms and vicissitudes of
the maritime life. Next came a whaling tour, during which he served in a variety of
capacities for a year, enduring an ever-rising tide of depredations that culminated
in his being chained belowdecks, without food or water for weeks, for theft,
attempted mutiny and insulting the honor of the whaler's drunken captain. Only the
intervention of a galley slave from the Barbados, who held the captain's affections,
and most importantly, brought him fresh water and salt cod at twilight, saved his
life.

Liberty

T
he 1770s:
great changes were blowing through streets of the colonial capital. The Crown's
troops had irrevocably stained Boston's cobblestones with the blood of Attucks and
others; the promise of freedom sweetened the air like incense. When Zion was freed
by his captain upon return to Sherburne, in Nantucket Island, instead of a duel to
restore his honor, the young man stowed away on a brigantine returning to the port
of Boston. Penniless, carrying on his person only a pocket pistol and several
cartouches he had stolen from the whaler captain's wares, and finding that both
Lacy's cousin and the safe woman had moved or been moved from their residences,
leaving no place to stay, for the town appeared to his eyes to have evacuated its
entire black population, Zion grew restless and proceeded to rob a tanner's store.
He was captured within hours by the Crown's authorities and confined, pending his
arraignment, to the city prison on Queen Street. After a short period of time, the
under-magistrate discovered that he was a fugitive slave, and returned him, pending
his trial, to Mr. Pennyman, now thriving handsomely with five shops throughout
Suffolk and Bristol Counties. Pennyman determined to get rid of him. His personal
scruples, however, did not permit him to entertain simply manumitting the slave. He
must first earn back his investment.

After Zion's conviction and brief imprisonment, he was again returned to
Pennyman, and the businessman ordered him to be flogged for his effrontery, which to
his preoccupied and rigid mind had assumed the character of outright treachery. He
then sent him south to work in a shop in Attleborough, far from the negative
influence of the sea or Boston, where the atmosphere fairly crackled with sedition.
Zion—who yearned either to take up residence in Halifax, which he had learned about
during his time at sea as a free man, and from there to ship out on a frigate bound
for parts unknown, or conversely to return to the only settled home he had known,
that of the Wantones, where he would be again among those who knew him best—did not
take kindly to this turn of events, and revolted. After only a week, he fled towards
Boston, following the coastal route and getting as far as Duxbury, where he stole
two cakes of gingerbread, a package of biscuits, and a pint of milk out of a
horse-cart heading north. He secreted himself in a nearby marsh. He was discovered a
week later, arrested and housed in a local jail. He swiftly broke out by eluding his
guard, commandeered a piebald, and headed south by southwest along the lesser roads
and trails. The local authorities again captured, tried and imprisoned him, not only
for his crimes but for his defiance of the social order, yet his realization of his
own personal power had galvanized him, making life insufferable under any
circumstances but his own liberation.

During Zion's second incarceration, Pennyman had quick-deeded his
ownership of the slave to a fellow reformed merchant, Simon Warren, of Boston, who
in return promised to pay full, rather than wholesale, price for several cases of
contraband liquor Pennyman was trying to unload. Zion left jail in May of 1772, and
for a brief spell worked agreeably under Warren. Within the year, however, during
which the enslaved man resumed a life of debauchery, including but not limited to
periodic flights to Middlesex and lower Suffolk Counties, allegedly fathering
several children by white, Indian and Negro women, drunkenness and brawling in the
streets of Boston, celebrating on the Sabbath day, breaking curfews, threatening
shopkeepers, openly praising London, and selling wine stolen from his master, Warren
found the situation so unbearable that he gave him to another merchant, his second
cousin, Job Hollis, of Boston.

Hollis, who had once held positions of prominence in the
shipbuilding trade in Marblehead, was now reduced to running a scrap metal-working
and trading shop on Lynn Street near the Hunt and White Shipyards. Possessed of an
increasingly liberal mindset, and realizing almost immediately that he could only
loosely control Zion, he afforded his charge some berth by giving him traveling
papers. With these the slave immediately took the widest latitude, for had not the
Reverend Isaac Skillman preached in that very year that “the slave should rebel
against his master”? One midday he took Hollis's horse and a fiddle he had bought
with some of his earnings, and rode out to a cornhusking at Medford. Here his
singing and strumming, striking appearance, and lively manner at the husking hall
attracted the attentions of a number of the local women. The one on whom he set his
sights, however, was a married white lady in her late 20s, Ruth Pine, of evident
gentility. She coldly rejected his serenades all afternoon. By the early evening,
armed with rum, he demanded that she accompany him back to a local inn, a suggestion
that visibly offended her, leading her to denounce him in the strongest terms
possible. He responded by slapping her so hard that she passed out. This led to a
great commotion in the hall, wherein there were numerous calls for the Negro's
death. He promptly fled. Pine's husband, a stout local farmer, was enraged that his
wife might be so mistreated by any man, let alone a black one, and even more
incredibly a slave. He pursued Zion on horseback all the way to Boston, where he
finally overtook the offender and engaged him in a battle of fisticuffs in Orange
Street, the city's main artery. An officer of the courts walking by glanced at the
boxers, then continued on his way. Within minutes Zion had reduced Pine to a heap of
bloodied flesh and linen. To celebrate, he mounted Pine's horse, his own having
galloped off, and proceeded to Cambridge, committing a series of burglaries of homes
and carriages along the way.

Bounty

I
tems stolen: a bottle
of rum, several pieces of jerky, a tricorner felt hat, nine pounds sterling four
shillings, suttler's markee, some chocolate, twenty pounds sterling, a flask of
French brandy, a pair of moreen small clothes (which did not fit and were thus
discarded in the Charles), a man's white linen shirt, a leg of mutton, two weight of
salt pork, eleven pounds sterling six shillings, five pence, a carbine and two
pocket pouches, a magnifying glass, a map of the easternmost British provinces in
Canada.

Advertisement

A likely Negro Man aged about 18 or 19 years,

that speaks very good English

of great strength and brawn

sings and plays the violin

sold on reasonable terms by Mr.

Ebenezer Minott, trader over against

the Post Office in Cornhill, Boston.

(There were no takers.)

Spree

A
fter settling this
most recent plight with the Middlesex County magistrate, Job Hollis arranged to
place Zion on board a vessel bound for Virginia where he would be sold at auction
and his wildness might finally be whipped or worked out of him. Only under such
conditions would this slave learn respect for the common and hardworking citizenry
in whose colonies he had been fortunate enough to dwell, Hollis reasoned, and if
Zion continued in his ways down there, the penalties would be swift, and ultimate.
Hollis walked Zion, hands bound, the requisite papers pinned to the slave's tattered
coat, all the way to Hancock's Wharf, where the South-going vessel was to dock. He
wished the young bondman a safe passage to the southerly port, saying a prayer for
his soul as they stood before the open water. To drown out his master's voice, Zion
began singing. On this note of defiance, the exasperated Hollis departed. For an
hour or so the slave stood there singing and whistling on the wharf as the bailor
and a customs official sat lubricating in a nearby ale house. When the ship, a
frigate, did not arrive at the stated time, Zion charmed a Dutch whore strolling by
to untie his bindings, whereupon he set off to find the first loosely hitched horse.
As he ran he proclaimed himself free. Under duress one's actions assume a dream-like
clarity. An unattended nag stood outside a tavern, and off Zion rode.

After a spree which stretched from the city of Boston west to the edges
of Middlesex County, the slave played his worst hand when he committed lascivious
acts just across the county line on the person of a sleeping widow, Mary
Shaftesbone, near Shrewsbury. Having broken into her home and reportedly taken
violent liberties with her, unaccountably Zion did not flee the town, but entered a
nearby tavern and began a round of popular songs, to the delight of a crowd of
locals and the horror of the violated woman. The sheriff arrested him without delay.
When he realized the notoriety of the criminal he had in his hands, he suggested to
the local magistrate that, although this most recent felony had occurred in
Worcester County, the criminal ought to be returned to the General Court in Boston,
which had the apparatus to deal with such evil. The magistrate responded that given
the current worsening political situation in the capital, it appeared unlikely that
the slave's crimes would receive rapid adjudication. Mrs. Shaftesbone, demanding
justice, or at least compensation, therefore had word sent to Job Hollis, who was
negotiating the sale of his business in the anticipation of an assault against
Boston's northern waterfront. The violated widow suggested a cash settlement, with
the proviso that Hollis sell the criminal out of the colonies, preferably to the
French West Indies. Hollis, who still held title to Zion, agreed to this
arrangement, and collected him, now restrained in wrist irons, from the town jail.
They rode westward, where Hollis's real plan was to sell the slave down at Albany to
assure a good price and guarded transport down the Hudson. But on the way, in the
town of Pittsfield, they encountered the Hampshire County sheriff, who claimed to
possess warrants for the Negro from Worcester and Suffolk Counties. In the confusion
arising over the validity, scope and authority of the documents, Zion, as if aware
of the tenuous state of justice for blacks in New York State, seized his master's
musket, knocked both men out, mounted the sheriff's horse, and rode back
eastward.

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