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The Captain's Dilemma

  • Writer: Erin Pelicano
    Erin Pelicano
  • May 30
  • 19 min read

Prologue: Two Souls, Two Paths Paralleled

Along the quaint river channel of Chesapeake Bay, where the sweet sound of moving water and wind-rustled trees dance in the night, there stood a magnificent abode perched nobly upon a hill outside of the township of Lane between Milford Haven and Chesapeake Bay; its commanding presence graced the winding expanse of the intricate connected channels below.


This striking residence, a true testament to the artistry of Colonial craftsmanship, was constructed of warm tan bricks, each unique in hue and texture, accented by crisp white window frames that gleamed with resplendence in the soft light of dusk. The sloping roof, clad in graceful shingles, arched elegantly towards a stately entrance, which beckoned visitors with a promise of warmth and hospitality.


In one of the windows, framed by the golden hues of the dusk, a small girl sat perched with her elbows resting upon the cool, narrow sill. Her cherubic face was illuminated by the flickering flames of a nearby candle, which danced merrily in the gentle evening breeze. With blue eyes mirroring the vastness of the expansive waters beyond, she gazed longingly across the river, a realm filled with dreams and boundless adventures yet to be discovered.


Oftentimes, she found herself lost in reverie, contemplating the prospect of sailing those waters and exploring the world as her father had oft described upon his return from distant voyages — tales that swirled in her imagination like the gentle zephyrs skimming the surface of the water.


The candlelight flickered in a rhythmic dance, casting soft shadows upon the walls and marking the passage of time by the slow burn of its wick. Briar sighed deeply, her gaze momentarily returning to the open book resting upon her lap, its pages filled with grand tales of courageous captains and their remarkable exploits. She pondered whether she might ever aspire to be as great a sailor as the heroes depicted within those stories, her young heart brimming with a daring spirit.


Suddenly, a soft knock reverberated through the stillness of the room, and the door creaked open to reveal her father. He entered, a man in his middle years, whose broad and sturdy frame bespoke of strength and steadfast service upon the treacherous seas. His dark brown hair, flecked with strands of silver that glimmered in the warm candlelight, framed a countenance adorned with a neatly trimmed beard, accentuating kind blue eyes that shone with an affectionate warmth for his beloved daughter. Dressed in coarse but well-worn garments, typical of a seasoned sailor, he exuded an air of both pride and authority.


“Briar,” he spoke gently, a warm smile breaking across his face as he approached her. “It is far too late for a little one such as you to be awake. Your siblings have long since settled into their beds, preparing for the dawn of a new day.”


“I cannot sleep, Papa,” she confided, turning to face him fully, her tiny gown a disordered mess about her little legs, while her blue eyes met his with sorrow and longing. “I am too sad.”


“Sad?” he echoed, his brow knitting together with concern as he settled upon the edge of her bed. “What, pray tell, could evoke such sorrow, my dear girl?”


“You depart upon the morrow, Papa,” she replied, her eyes widening with an abundance of emotion. “And won’t be back for four years! I do not wish for you to go, not without me.” Her voice trembled with the weight of her lament, evoking in him the familiar ache of longing he had similarly felt in his restless youth. Yet, having navigated the tumultuous seas and endured the perils that came with such a life, he had garnered wisdom born of experience that illuminated the inherent dangers of the maritime world.


He lifted her tenderly onto his lap, his hand stroking her hair with the affection of a seasoned sailor calming the restless waves that were within his own daughter. He saw so much of himself in her, more than in his own son, whom he had hoped would take up the mantle when he retired, but Franklin had taken another route in life as a carpenter within Portsmouth. Nevertheless, with his second youngest of four children, his passion for the sea had begun to bloom, and it was a comfort to him.


“My dearest girl,” he began, his voice soothing as a gentle sea breeze. “Oh, how I long to have you accompany us aboard the Daphne, sailing beyond the distant horizon with us to places across the sea. Yet, you are still but a child, too young to labor upon a ship, and my captain holds a superstitious belief that a woman aboard brings ill fortune to the crew.”


“I can prove him wrong, Papa!” Briar exclaimed, her tiny fists clenched in unwavering determination. “I fear not the work, nor do I tremble before pirates or the British sailors! I can take care of myself—and of you!” Her innocent bravery elicited a chuckle from his lips, for he admired her indomitable spirit; yet, he recognized the naiveté that accompanied such fervor, for the world beyond the security of their home was rife with hidden dangers and daunting challenges, much like weeds thriving amidst a beautiful garden.


“Nevertheless, my dear Briar,” he said, meeting her bright gaze with warmth and solicitude, “it is of the utmost importance to exercise wisdom. You are still so young and tender, quite unable to accomplish even the simplest of tasks that the servants manage with ease, or what you undertake in the garden alongside the gardener Raphael. A sailor’s life requires far more than mere courage of the heart; it demands a considerable measure of physical strength to withstand the numerous hardships of the sea. Yet, I hold firm in my belief that one day, my beloved daughter, you shall grow strong and capable, provided that you heed the lessons I have imparted unto you. That day shall dawn sooner than you may perceive, and it will be all the more gratifying for your patience.”


“Yes, Papa,” she responded, resting her head against his broad and sturdy chest, her small arms enveloping him in a snug embrace. He held her closely in his warm embrace, gently rocking her back and forth, aware that this soothing motion would soon lull her into the realm of dreams.


“I shall miss you dearly, Papa,” she murmured, her voice gentle and drowsy. “Promise me you will write and regale me with tales of the Old World and the Mediterranean.”


“I vow, upon my very soul the Good Lord created, that I shall share every detail with you in my letters, dear Briar. And I long to hear of your own adventures here in Chesapeake Bay. While I am far from home, I will crave the comfort and warmth of our beloved abode.” A smile graced her lips as her tiny fingers curled affectionately around the fabric of his vest, a bond between them as steadfast as the ties of kinship.


Briar adored her father, her allegiance to him more profound than any connection she felt to her mother or siblings. When he ventured away, it seemed as though a part of her accompanied him, leaving her in a world that often felt too ordinary, bereft of the exhilarating thrill of adventure.


As her eyes grew heavy with the sweetness of slumber, he began to sing a familiar shanty, the words flowing forth like a gentle lullaby that enveloped her in the warmth of a tender embrace. Sleep began to beckon her, drawing her into a resplendent sea of dreams where her imagination took flight, conjuring up visions of grand exploits shared with her father.


In the waking world, he gently lifted his sleeping daughter, carefully placing her back upon her bed, tucking her snugly beneath the covers, and brushing a stray lock of hair from her cheek with utmost tenderness. He lovingly closed her book and extinguished the flickering candlelight, casting the chamber into a peaceful darkness. For a fleeting moment, he lingered, gazing upon his daughter with a soft smile gracing his lips as he whispered:


“Sleep well, my cherished Briar. May the Lord watch over you as you journey through your dreams.”

 

~ * ~

 

Meanwhile, further down the channel in Portsmouth Harbor, the roaring sounds of the lively town resounded throughout the dimmed evening of a chilling cold night; a cacophony of sounds thrived in the vivacity of a small portion of Portsmouth and Norfolk, located at the head of the harbor.


Voices filled with laughter and friendly chatter wafted through the air as strangers passed by with varying degrees of haste, while the clattering of horses’ hooves against the cobblestone streets intertwined with the rhythmic creaking of cartwheels. Beyond, the gentle humming of the sea as it struck the sturdy walls of the harbor, coupled with the soft rocking of ships moored at the docks, completed the harmonious chorus of sounds that the town offered.


Yet, deep within the confines of this bustling enclave, as the evening darkened into the depths of night, the eyes of passersby were drawn to the slow, shuffling gait of a child whose feet were encased in tattered deerskin shoes, riddled with holes. The small figure meandered onward, his gaze fixed upon the ground, a silent testament to the physical and mental distress he suffered. His hair, a wild cascade of black, brushed the tops of his ragged shirt, which, like the rest of his garments, bore the marks of wear and soiling from days spent wandering the streets, enmeshed in profound solitude.


Those who chanced upon the unfortunate lad quickly averted their gazes, repulsed by the heart-wrenching sight of a young soul in dire need, a child who endured tribulations that few could comprehend. However, amidst the throng of indifferent townsfolk, one figure watched the young boy with intense interest, cautiously trailing him from a distance, lurking in the shadows of the edifices like a stoic cougar keenly focused upon its unsuspecting prey. The child remained blissfully unaware of the man pursuing him, whose countenance was marked by a troubling expression that suggested devious intentions.


As the boy continued his desolate journey towards the harbor, he eventually halted at the corner of a dwelling; visibly weary, weakened, and gripped by hunger. He leaned against the wall for support, his small frame draped in sorrow. The man halted just a mere pace behind, remaining shrouded in darkness, his resolution solidified. With deliberate quietude, he reached into his coat and retrieved a foreboding implement before stepping towards the unsuspecting lad.


With an unseeing gaze cast up the street, where attention was drawn elsewhere, the vulnerable child was swiftly silenced by a formidable hand that dragged him away into the terrifying embrace of the night.


Docked at the harbor of Portsmouth, an aging, single-masted Sloop-of-War, bearing the fading name of Swallow inscribed in white lettering upon the dark wood of her captain’s quarters, stands as erect and sound as her years allow. A vessel of swiftness and pride, she carries immense significance amidst the fledgling Navy of America, dispatched for the most consequential of tasks.


Onboard, the men stationed on watch revel in a tranquil evening on the main deck, their vigilant eyes ever scanning the horizon, and their keen ears attuned to the rhythm of waves and whispers from the shore. Below deck, the idle crew engages in merriment, their spirits lifted with a jubilance born of camaraderie, some still encumbered by the affections of their wives and sweethearts, hidden away in the ship’s secluded quarters. A strong tobacco pipe is enjoyed by many, while one among them plays a few lilting tunes upon an aged accordion, joined by his mates in harmonious chorus if they are familiar with the shanty at hand.


Behind a slender door into the captain’s quarters, guarded by a youthful marine, an elder man with a mane and beard as gray as the raging storm rising over the sea studies navigational maps and a compass. With meticulous care, he delineates a course upon the chart, preparing for the impending voyage that shall bear dispatches for his Commodore. This is a man whose weather-beaten visage tells tales of tumultuous encounters with the sea, having faced British foes and Spanish alike since the dawn of his youth.


Yet, the inexorable passage of time seeps through the cracks of his spirit; he bears the weight of weariness akin to that of the ship he commands, despite still being in the middle of life’s journey. The raucous laughter of his crew beyond the door draws him momentarily from his contemplations, finding this newfound cheer both strange and disconcerting, even taking notice of the cackling of the women akin to hags across the deck. At that moment, a rapid series of knocks rang through his cabin; a sound resounding powerfully from a great hand.


“Come!” the captain had called, his voice weary, low as a grumble. The door had swung ajar, revealing a broad man with rolled-up sleeves, displaying an array of tattoos that spoke of adventures and hardships. He had leaned into the captain’s dimly lit quarters, his countenance a mixture of disappointment and concern, a sight most surprising to the captain.


“Captain Franklin, I beg your pardon for the intrusion, sir. You must come forth and witness this.” A sense of perplexity had washed over the captain as he rose, instinctively following the man out onto the deck. There, his attention had been drawn to a commotion amidst the laughter of his men, gathered in a huddle upon the upper deck, displaying an unseemly gaiety reminiscent of schoolboys at play. Even his two Midshipmen, mere lads of late adolescence, stood agape, captivated by the revelry.


As the captain approached, urging silence with a furrowed brow of concern, he discerned that they were passing a small form amongst them, and his weary demeanor had shifted dramatically to one of grave anger intermingled with astonishment. It was the small, helpless child they had so callously tossed from one to the other, his eyes crudely blindfolded, and his little wrists bound tightly by coarse rope.


The child gasped, squirming at each pass, each rough grip of a man’s arm upon his shoulders, each precarious chance of stumbling over his own feet, teetering on the edge of falling upon the deck. In his desperation, he had strained to free himself from the entanglements that bound him, fear etched upon his youthful face. The men, in their insensitivity, had paid little heed to the frightened child, encouraging the five hands to treat him with greater roughness, whilst the women draped their shawls of worn silk or coarse wool across his visage, mocking the innocence of the lad as the sailors took turns holding him aloft.


“What in the blazes is occurring here?!” The captain boomed with a voice as gruff as an angry bear, bringing immediate silence to all in his presence. The unfortunate child, having been accidentally thrust into the arms of the stout man beside the captain, was gently drawn back a few paces from the other men. The trembling boy, clearly exhausted, quaked in his arms. The captain stood there, seething with fury, his countenance rendering the faces of his crew pale with dread as they began to question their own conduct. The only sounds to penetrate the oppressive silence were the scurrying of rats and the creaking and moaning of the ship’s hull.


“Who bears responsibility for this wretched affair?” he demanded, his tone low yet infused with a palpable anger at the misdeeds his men had been caught committing. Not a soul dared to speak up, even though they all knew that the perpetrator stood proud and silent amongst them, wearing a frown of insolence. The rest of the crew wore expressions of a mixture of shame and terror as the captain’s penetrating gaze roved across their faces, searching for the guilty party. Even the women, adorned in heavy makeup and bearing the marks of age, remained silent, their expressions one of indifference.


“We’re a Naval vessel, not a pirate sloop!” he growled, surveying his men as many of them seemed to wither under his scrutiny. “Unless thou wished to endure half-rations for a spell, or even a sound flogging, I urged thee to reveal the one among you responsible for this insubordination!” The silence dragged on, thickened by fear and shame, until a voice from the main deck broke through the oppressive air.


“Ask Dodson, sir. He brought a full sack aboard from the shore and kept its contents a secret!” The words crashed through the tension like a wave breaking on a rock. It was the voice of First Lieutenant Andrew Teich, who raised the accusation toward the captain, casting a glance at the man who had dared to abduct the child.


“Do enlighten us, Mr. Dodson, as to the motivation behind this act!” he demanded in a somewhat calmer tone, though the fire of disappointment and anger still blazed in his eyes. With every eye now turned upon him, the man stood his ground defiantly.


“What justification could I offer?” he replied, a smug arrogance lacing his voice as he rolled his shoulders. “I saw him looking wretched whilst wandering through town, sir. One hardly encounters a Red-Skin beyond their tribes; I thought the boys might find him an amusing diversion.”


“He’s a mere child, not a damn performing monkey!” the captain erupted, his voice rising in intensity. “What thou hast done was not only irrational but surely must have thrown a mother into a frantic state over her missing boy! Thou’re a scoundrel for perpetrating such an act, Mr. Dodson! And thee, ladies—if I could even accord thee such a title—how dared thee partake in this and chuckle it off! I doubt thou wouldst have remained unfazed were it to be one of thy own children!”


The women’s faces fell, turning their gazes anywhere but towards the captain or the boy. Most of the sailors were equally evasive, as Dodson’s explanation rang hollow and devoid of reason. Their actions revealed themselves as unjust and cruel in the eyes of their superior.


Turning away from them, the captain stooped down to the frightened boy, who remained deprived of sight, his wrists bound tightly. The captain took a dagger extended to him by the stout man and carefully severed the bonds that confined the child’s hands before lowering the blindfold from his eyes. The boy’s small, dark orbs were red and swollen, stained with the remnants of tears, blinking as they adjusted to the sudden brightness cast by the lantern above him.


“It’s quite alright, dear boy,” the captain soothingly said to the startled child, who stood frozen amidst the throng of sailors surrounding him. Despite the bewilderment, the lad remained silent, his lips sealed and no cries escaping his throat. The captain’s heart sank as he beheld the pitiful sight of the child — clad in tattered rags, mud crusted upon his garb and skin, dust enshrouding his face and limbs. Scratches marred his arms and legs, while his right cheek bore a fresh bruise and a harsh rope mark encircled his neck. Some wounds seemed recent; others showed signs of an agonizing healing process. This child had endured unimaginable horrors.


“Mr. Finley, take our little guest into my quarters. I shall join thee shortly to assist thee with him. Provide him with a blanket and, perchance, some garments superior to these rags,” instructed the captain, his voice a blend of authority and compassion. The broad-shouldered Mr. Finley nodded, his large, gentle hand resting upon the child’s thin shoulder, feeling the frail bones beneath. Although the child displayed evident reluctance to depart, he allowed Mr. Finley to guide him toward the captain’s quarters. The captain then directed his attention to his crew.


“Mr. Dodson, gather thy belongings and seek employment aboard another vessel. As payment had been rendered that day, thou wouldst receive thy final wages, but I would write no letter of recommendation on thy behalf.” 


“What the devil? Ye’re choosing a savage over one of yer own?” Dodson protested, incredulously. 


“I am dismissing thee due to your disgraceful conduct towards a child!” The captain’s voice rose, laced with indignation. “Kidnapping’s a most heinous crime, thy witless fool! It mattered not his lineage; what thou had perpetrated was beyond cruel. The boy had endured sufficient anguish already, as was clear to all, and thy actions had plunged him deeper into despair and us into peril. This marked thy final act of defiance on my ship. Now, out with thee!”


No member of the crew rallied behind Dodson in defense of his misguided actions, and he begrudgingly gathered his sea chest from beneath his hammock, collecting his effects before ascending the stairs and departing, muttering curses against both the captain and the innocent child. The captain commanded the women to disembark as well, and the marines escorted them to their boats. He turned to the remaining crew, arms crossed firmly against his chest. 


“Let this serve as a lesson to all ye men this night. A similar transgression will earn thee flogging and immediate departure from my ship. Is that understood?” 


“Aye, Captain!” they responded in varied tones, acknowledgment ringing through the air.

“Now be off with thee, and ready the ship to set sail at first light!” The crew dispersed to fulfill their duties, while the captain called to his First Lieutenant, assigning command for the night to the eldest Midshipman, who hesitated but complied with the order. Once matters had settled, the captain approached his quarters as Mr. Finley stepped out, intent on retrieving some provisions from the galley and his personal quarters. 


“How fares the boy, Connor?” the captain queried in a hushed tone, noting the deep sigh from his steward in reply.


“Still quaking and silent, I fear the lads have frightened him into a state of muteness,” Mr. Finley replied, his expression troubled. The captain nodded, casting a glance through the crack of the door to glimpse the boy, seated upon the bench beneath the stern windows, a mournful expression etched upon his countenance. The child trembled all wrapped up in the blanket, yet clearly was still cold and frightened. 


“Let us procure better garments for him and assist in cleaning him up. Do we possess anything suitable?” Mr. Finley turned his gaze back to the child.


“I shall see what we can muster. I may need to modify some items from the stores intended for the Powder Monkeys; he’s thinner than a krill. No doubt he's famished, sir. I shall prepare a stew for the men and boys, and ensure ample provisions are set for him as well.” 


“I thank thee, Connor,” the captain replied before entering his quarters, while Mr. Finley made his way to the kitchen and his personal quarters to gather the necessary items. The child looked up at the captain, eyes wide and rimmed with red. The captain, aware of the boy’s unease, found himself at a loss for words. As a widower with no offspring of his own, he lacked familiarity with the needs of a child. With a heavy sigh, he drew a chair closer and sat before the boy, resting his arms upon its back in a gesture of empathy.


“I'm truly sorry for what had transpired, boy,” the captain exclaimed, clearing his throat, wishing to grant the child at least the dignity of an apology for Mr. Dodson’s most disgraceful conduct.


“I do not tolerate such behavior, such acts are not favored in the Navy; for we were not pirates but rather a ship of our nation, sworn to serve all who resided upon our shores. The actions of that man stood contrary to our laws.” The lad, with brown eyes full of apprehension, cast a fleeting glance upward before returning his gaze to the hole-filled, worn-out shoes adorning his feet. The child’s lack of reply stirred a deep concern within the captain’s heart.


“Can thee comprehend my words?” the captain inquired gently. After a moment spent observing his feet, the small boy nodded. “Art thou perhaps mute, then?” He lifted his gaze and shook his head in the negative.


“Ah, I see. So, thou simply lack the inclination to converse with a stranger?” At this, the lad offered another hesitant nod.


“Fair enough, young one. After all that’s happened, I blame thee not. Allow Mr. Finley and me the privilege of caring for thee this night. He’s preparing sustenance, warm water for a bath, and procuring better garments for thee as well. Those rags thou wears has outlived their usefulness for far too long.” The boy regarded the captain in silence for a moment, and then, with a voice as timid as a whisper, he croaked, “Why?”


“Why indeed?” The captain responded boldly, tilting his head toward the port side. Dropping his shoulders in resignation, he continued, “Call it charity, call it pity, whatever title you wish. Before me sits a lad resembling a beggar, who appears as though he had traversed the bitter depths of hell and endured yet another trial aboard my vessel unbeknownst to me.”


“M-most people… they… they chose to ignore me, for my parents… I bear the likeness of Mama and Papa,” came the boy’s quavering reply, his voice straining as he struggled to hold back tears that threatened to spill from his reddened eyes.


“No doubt thy mother grieves for you still,” the captain responded, contemplating that it might have been prudent to return him home ere they set sail. “Where’s thy mother at that moment?”


“S-She’s laid buried, alongside Grandfather.” A profound sorrow etched itself upon the boy’s visage, mirroring the captain’s own heavy heart.


“I lamented thy loss, young lad. Is there no one else to care for thee? What of thy father?”


“H-He was taken from us by the sea, not long after I was born into this world.” The captain nodded solemnly, coming to realize that this small child was an orphan, bearing the weight of the world upon his fragile shoulders. The lad fixed his gaze upon his battered and blistered feet, uncertainty engulfing him as he contemplated his ability to survive in such dire circumstances. He was cast out by his tribe for possessing the blood of another lineage, and the villagers—a cruel lot—scoffed at him, turning their eyes away from the visage of his mother reflected in his countenance. At times, they treated him as though he were a bedraggled, sickly beast, riddled with disease and vermin.


The thought of the sea swallowing him whole danced in his mind as a tantalizing escape, for it had been his original destination prior to his untimely abduction and forced voyage aboard this weathered sloop. The captain, rubbing a hand through his grizzled hair and across the nape of his neck, found himself grappling with the enormity of the decision that lay before him. Yet, the gravity of his pity for this unfortunate child far outweighed his thoughts of abandoning him to a fate even more grievous. Who knew? Perhaps this act of kindness might impart valuable experience in the trials that awaited him in the future.


“What’s thy name, son?” inquired the captain, his gaze fixed upon the small child before him, who clutched the edge of a warm blanket, a flush of shame coloring his cheeks. “I… have no name,” came the boy’s meek reply. 


“No name? And thou art but five? Six summers?”  


“S-Seven,” he replied, a tinge of defiance in his voice. The captain raised a brow in surprise. 


“Seven? And thou hast no name? How did thy family or others address thee?” The boy shrugged slightly, as if the inquiry pained him. “Little One or Boy, as you do.” 


“By the heavens!” the captain muttered, leaning back with an audible sigh. He regarded the child, whose countenance bore the weight of gloom and uncertainty, pondering in silence for a spell. “Well,” he finally declared, leaning forward to speak with a softer tone, “it shall be my honor to bestow upon thee a name, young lad. Art thou of the Christian faith?” 


“Do you refer to the belief in the man upon the cross?” he inquired, his wide eyes searching the captain’s face. 


“Aye, then thou art indeed,” the captain nodded slightly. “Let it be thus; Anan shall be thy name, an ancient name from the Scriptures. As for thy surname, I deemed it fitting to grant thee the appellation Catch, for thou hast been caught and brought aboard my vessel.” Anan shrugged his small shoulders in reluctant acceptance, focusing intently on committing the name Anan to memory. 


“Well, Anan,” the captain continued, “since thou hast no one to look out for thee, wouldst thou care to join my crew?” 


“I—I have no knowledge of sailing, though,” the boy replied timidly, glancing around the confines of the captain’s cabin, which appeared vast and daunting to his young eyes. 

“Fear not! Thou hast the sea legs about thee; that’s a fine beginning. Mr. Finley and I will ensure that thou art looked after, and we’ll teach thee the ropes, instructing thee in the ways of seamanship. While thou art young and small, I grant thee that, and we ordinarily will not take lads under the age of twelve aboard to learn the trade. However, I believe thou will suit well as a powder monkey. Thy wages shall match those of the other lads, with the same treatment afforded to thee, albeit with less sternness. Dost thou believe thyself up to the task?” 


Anan gazed into the weathered face of the man before him, who offered not only a challenge but, ultimately, a far brighter future than the one he had previously known. With great care, he rose to his feet, weary and still clutching the blanket around him.

 

“Yes, sir!” he declared with a newfound resolve.

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