Oregon Territory 1849
“I’ll take all the shovels you’ve got!”
Rainwater ran off the sailor’s sopping oilskin slicker.
A black‑twill cap shadowed his eyes.
He stood in the doorway of Oregon City’s general store. A rare sight among Willamette Valley wheat farmers, he stepped in from the downpour.
Leaving a trail of muddy boot prints on the pinewood plank floor.
At the store's counter, an elderly gentleman paused in casual banter with a customer to eye the stranger in curiosity and speculation.
Behind him and to the left stood a broad-shouldered woman, older, her long black hair streaked with gray and braided at the nape. A worn gray shawl draped her shoulders, sharp black eyes set beneath a lined brow, watchful and busy.
The shock of white hair adorning the watching gentleman's head identified the renowned proprietor, Dr. John McLoughlin.
The Indians called him John Pee‑kin—the White‑Headed Eagle of the Whites.
His establishment bore the reputation as the ‘last stop on the Oregon Trail.’
Tom Bodeen had journeyed here all the way up from California, determined to negotiate a deal with this venerable figure.
And the woman? Likely Marguerite McLoughlin herself—John’s wife, and by most accounts, sharper than any blade behind that counter.
Confidently, Tom traversed the creaking planks, taking in the scent of freshly cut lumber mixed with the aroma of roasted coffee grounds, in the rustic atmosphere.
As he passed by the lantern oil and dry goods, Tom’s attention remained fixated on the prize; a picket line of shovels propped against a log wall.
“I hear you’ve got the best shovels west of the Mississippi.”
Tom tipped his hat, offering a slow, easy grin that had disarmed gamblers and gunslingers alike from San Francisco to Sacramento.
Hailed by others as ‘the most honest man in the territory,’ John assessed Tom with discerning eyes for his pleasant demeanor.
“And what have you brought to trade, sir?” John’s gaze scrutinized Tom’s unfamiliar appearance.
The customer bystander, bearded with unkempt hair and a stained deerskin jacket, wiped his nose on his sleeve and watched the interaction unfold with the curious desire to learn why Tom needed all those shovels.
His unclean appearance and unmistakable body odor rendered him a quintessential settler—a familiar sight in these parts.
“I have British trade goods fresh from Vancouver’s Island,” Tom announced, resting both hands on the roughly hewn counter, ready to do business. “Thought I’d make a splash in your corner of the world.”
“Did they provide you with your cargo list?” John’s eyes rested on his inventory ledgers, while thumbing through them.
“They did. They were well-acquainted with your needs,” Tom assured him. “And I’m sure you’ll find my prices as charming as my company.”
“And does it include Hudson Bay flour?”
“It most certainly does. I always aim to bring a little bit of the best from every corner I visit.”
John finally looked up from his ledger.
“Then we have a deal. But I am curious, how much duty did you pay on that flour?”
Tom responded with a shrug. “Nothing.”
“Nothing? Pray tell, how did you accomplish that?”
“Oh, I simply raised the stars and stripes and sailed right on by U.S. Customs at Astoria. As an American, I am not obliged to stop.”
“Except when carrying Hudson Bay flour,” John admonished him in reminder.
Tom smiled with a hint of amusement, then leaned in slightly, his voice taking on a more confidential tone. “People keep telling me that,” he shared. “But somehow, I always manage to forget.”
“You’re a smuggler, aren’t you?” John’s gaze returned to his ledger, searching for yet another page while dipping his quill pen.
“Some might call it that. I prefer to think of it as finding opportunities where others see obstacles.”
“Have any notion of the sum you saved in duties?”
“I’m afraid not, why do you ask?”
“Each time the Hudson Bay Company’s supply ship docks at Astoria, it pays $24,000 in U.S. taxes. I should know—I ran their trading post for over two decades.”
“Well, perhaps the company’s vessel ought to consider not stopping there then?”
“Not my decision anymore,” John replied, stepping away from the counter to count his inventory of flour sacks. “Don’t worry, I’ll still give you a good price for that flour.”
“Put me down for some of that flour,” the other man quickly spoke up.
“Already did,” John told him, coming back. “So, how’d you manage to navigate the river’s current?”
“I have a bateau,” Tom responded of his shallow bottomed sailboat.
“She must be mighty swift to sail upstream.”
“She’s the fastest there is,” Tom boasted.
“If you don’t mind my asking,” John inquired; his curiosity evidently piqued, “how much cargo does she carry?”
Tom sensed an underlying interest. “Four tons. That’s her current load. From here, I’m headed to Fort Vancouver to sell the rest.”
“I see. And do you plan on purchasing their shovels as well?”
Tom nodded.
“To sell them in California?”
“Yes, indeed. There are a lot of gold miners eagerly awaiting them down there.”
Marguerite’s voice cut through the room like a blade honed on memory.
“Plenty of men went south chasing gold like dogs after bones. Left their native wives behind here to plant wheat and bury children.” She didn’t look at Tom when she said it. She didn’t have to.
“Sorry to hear that,” he replied, like a man who’d just stumbled on an unwanted story.
“Figure you’ll sell them for quite a profit, do you?” John interrupted, eyes steady on Tom.
Tom gave him an affirming nod. “That is my intention.”
“You’re Tom Bodeen, aren’t you?”
“You know me?”
“Heard of you. They say you’re a brave man who never lies.” John checked off another entry on his ledger. “A handsome devil, too. Tell me, sir, what compels you to venture here?”
“Like everyone else, money,” Tom answered.
“Oh, but you’re not like everyone else. They’re buying the shovels. You’re selling them,” John dryly observed while calculating his offer.
“I suppose.”
Like the majority who ventured to this untamed land, Tom desired wealth. However, he had no intention of gambling on striking gold when the odds were mostly just holes in the ground.
“No supposing about it. You are,” John affirmed, stepping around Tom to count the shovels displayed on the wall. “You didn’t come out here to search for gold.”
“No, sir. I plan to make my fortune carrying freight,” Tom said.
He wasn’t here to gamble with a pickaxe—he meant to profit off those who did.
“What other cargo do you plan on transporting back? We don’t have four tons of shovels.”
“I notice you have an abundance of lumber,” Tom pointed out.
“You have a keen eye, sir. Indeed, we do. But suppose I told you how you could make tenfold the profit you would on those shovels. Would you be interested?”
The offer, coming from the most respected man in Oregon Territory, caught Tom’s attention. “I’d be a fool not to be.”
“There’s more money to be made hauling freight here than in California. Your boat is too small to carry enough lumber. In the last six years, we’ve only had a total of seven ships arrive. Yet this year alone, we have scheduled fifty from California, all willing to pay any price for grain and lumber. They’ll put you out of business in one trip. Captain Emory's brig is already on the way here and able to carry more cargo than you can manage.”
“Well, I had sort hoped to beat them to the punch, Emory included,” Tom responded. “But supposing I didn’t. What do you propose?”
Marguerite sniffed, as if it were an old story to her, folding canvass. “You men are always hoping. And it’s always someone else gets to pay the price.”
Tom looked over at her, noticing she moved like someone who’d heard too many promises and trusted only results. And wasn’t convinced he’d be any different.
John returned to the counter, running a finger down his ledger page. “Take your boat up the Columbia River for a load of produce,” he suggested. “Be one of the one’s selling grain to those ships.”
“Upstream?” Tom scoffed, shaking his head at the mere suggestion. “Have you forgotten there’s an Indian war going on up there? I had planned on keeping my scalp. I’ve grown rather attached to it. I'm just passing through. Not getting involved. Besides, there’s no Indian war in California.”
“Heard about the war, did you?”
“Everyone has. It’s the talk of California.” Tom showed his understanding. “Some wagon train on the Oregon Trail came down with measles and diverted north for Dr. Marcus Whitman’s Mission.”
His eyes met the other customer for confirmation and whose head bobbed in ready agreement with his facts.
Tom continued, now fully engaged in the narrative. “That’s when the Cayuse wives of the British Hudson Bay Company's employees at nearby Frenchtown arrived to trade with the settlers for linen and cotton shirts. Only they got more than just shirts—they got measles.”
“You’ve heard correctly,” the bearded customer spoke up. “Half the women died, nearly all the children.” His missing front tooth showed. “So the Cayuse tribe struck back—killed Marcus Whitman, his wife, the men with the wagon train. Ransomed the rest.”
“I believe they called it the ‘Whitman Massacre,’” Tom recalled.
“Hostilities ceased over a year ago,” John informed him, completing the order. “I want a sack of flour for each shovel.”
“Agreed!” Tom confirmed, shaking hands on the deal before inquiring further with skepticism, “So you're saying the fighting’s stopped? What about the measles? The outbreak and the massacre? Those were no small matters.”
“Ended just a month later,” John confirmed.
That perked Tom’s interest. “You’re suggesting it’s safe to venture up there?”
“It should be,” John confirmed.
“Suppose I undertake this journey. Will I be transporting the same cargo I have now?”
“Yes, the very same. Except for the flour—that stays here,” John explained, making his ledger entries as he spoke, “Think about it,” he said, still writing. “The Hudson Bay Company's forts upriver will purchase the rest of your cargo and then let you take the money and buy all the produce you can haul back to Astoria to sell to those ships from California.”
Tom took further interest. “And you claim I’ll earn ten times what I can make on these shovels? Because I’m pretty sure I can earn quite a lot on them.”
“You can almost name your price. Salem will pay you $6 for a bushel of wheat you’ll pay 80 cents for. You’ll be paid in gold.”
Tom leaned in closer, cautiously optimistic. The conversation had shifted from shovels to much grander possibilities. He wanted to hear more.
“I'm intrigued, but isn’t the Oregon Trail impassable due to the warring Indians? I don’t want to be another cautionary tale of those killed.”
“It is, but you'll bypass the trail with your boat by using the river,” John said. “I’ve got a chart you can use.”
He went out back and brought it forth to roll it out before him.
Tom took a close perusal of it, admittedly impressed at how good it was. “Someone went to a lot of trouble to make this,” he noted with a whistle of admiration for it. “It must have cost you a fortune.”
The good doctor eyed him without answering, waiting for his decision as the rain drummed off the roof.
Tom’s mind weighed the chart from every angle. He was visibly torn by the temptation, but had his doubts.
“No, I'll stick with California,” he finally decided, shaking his head. “It’s too risky. The man who sold you this did so for a good reason—if he tried using it himself, the warring Indians would kill him on the river. So, he sold it to you, instead.”
“He sold it because his bateau’s too slow to get past the natives. Yours isn’t. Do you think you’re up to the task?”
Again, the promise of profit lured Tom as he studied the chart, shifting his weight in uncertain hesitation.
“Well, it’s a mighty tempting offer, and it is a good chart. I’ll grant you that, but you’ve had nearly two years to do it yourself and still haven’t done it with, or without, this chart. So why haven’t you?”
“I told you. Our bateau is too slow. But if the natives concern you, we stopped selling them gunpowder a year ago.”
“And you think I can get past them?” Tom asked of either man.
“You can if your boat is as fast as you say it is,” said John.
“It is,” Tom mused, noticing the other man hadn’t answered. “Yet it seems to me an entire regiment of militia tried to take on those same Indians and got themselves whooped.”
“You’re talking about Colonel Cornelius Gilliam and his outfit,” the customer spoke up, nodding in ready agreement. “Yeah! You heard right. He got himself more than just whooped, he got himself killed.” He shook his head in grim remembrance of what happened. “The rest all came a running back here like a bunch of dogs with their tails between their legs.”
“That’s true,” John said without argument. “But let me show you something, something they didn’t have then.”
He again went into the back of his store to return with a surprising item and set it down on the counter in front of Tom. “Do you recognize what this is?”
Tom paused, studying the unexpected sight. Indeed, he did know what it was. They had only just come out. His gaze lingered in curiosity, the gleam of dollar signs already registering in his eyes.
“Do you mind if I look it over?” he asked.
“No. Go right ahead! It’s yours if you want. It comes with the chart.”
Marguerite looked on, said nothing, but raised a disaproving eyebrow.
Tom picked it up if only for the privilege of its inspection, the story of Colonel Gilliam’s gruesome end lingering in his mind. Yet this opportunity was his chance to outpace his competitors and secure his fortune.
He traced the textured surface of the linseed oil finish, the intricate grain of the wood, and admiring its fine workmanship and design. This was a tempting offer. When the odds are against you, always put them in your favor, and the good doctor had just done so.
“I get both?”
“You get both.”
“And you’re sure the Indians don’t have gunpowder?” Tom asked.
“Not for over a year.”
Tom searched the settler's face to see if he agreed. When he presented no argument, this changed everything. He had only one question. “How much?”
“I’ll make you a deal,” John offered. “That, and this chart, no charge, for a share of your profits.”
The offer hung in the air between them with the weight of gold, not in California, but just upriver.
Marguerite returned to folding canvas, but not before Tom caught the hint of a smile—wry, quiet, and almost pitying.
As if she already knew how this would end.
