Side Trail
Captain Alonso Shepherd
Steve Levi


Side Trail Story

Alonso Shepherd, Captain Alonso Shepherd, was the master of the Bella Ann. It was his ship. It might have been owned by the Portland Steamship and Lighterage Syndicate but he was god for every tick of the clock from the instant the ship left the Portland dock until it returned two weeks later. He had the power of life and death over every crew member and anyone else on board. That being said, he was the perfect match for his job. He knew the size and location of every bolt and water door on the steamship. He had personally ordered every pound of coal for the boiler, purchased every inch of every cable and steam pipe below deck and supervised the installation and repair of every foot of deck plank from bow to stern. He could walk the length of the ship below deck in pitch blackness and the length of the ship above deck in a pitching sea.

And he was blind as a bat.

Captain Alonso Shepherd, lord of the Bella Ann and god on the open sea was blind. His affliction was so bad that he could not see the hundred pound crates of whiskey labeled as “canned peaches” that were loaded into the hold of the ship in Portland. He never saw the crates unloaded, which was natural, of course, because one could not see cargo offloaded that had never been on-loaded. He also could not see the beaver pelts and dried fish that were loaded into the Bella Ann in Hootlani. He could not see any of this cargo because it was not on his official cargo manifest and therefore it did not exist because, by Syndicate rules, liquor of any kind was not allowed on any of the one ship owned by the Portland Steamship and Lighterage Syndicate. The Syndicate presented the manifests to the Steamboat Inspection Service whose three inspectors for 30 ships a day looked into the hold of the Bella Ann and asked if everything on the manifest was in the hold. Captain Alonso Shepherd would affirm that he had seen every crate on the manifest loaded.

Which he had.

He was not asked about cargo he had not seen loaded because, if he had not seen it, how could he answer that question? The Steamboat Inspection Service stamped his manifest, charged a clearance fee and the Bella Ann was off to Alaska. Arriving from Alaska, the ships were not even searched. What could anyone smuggle from Alaska that had any value in Portland anyway? Oddly, the job of steamship inspector was a highly prized job; how else could some inspectors live so well on such a modest income?

Having been at sea since he was 14, Shepherd had a steamer trunk of stories, most of them exaggerations of the truth but as no one complained, Shepherd kept telling them. He started as a cabin boy on the whaler Reliance which harpooned no whales for the simple reason that it was not designed to be a whaling ship. It was a ship whose name changed on a monthly basis because it was running guns to the Confederacy out of New York, Boston and Baltimore. The ship never had a close call with the United States Navy for the simple reason that the captain of the oft-name changing ship had been raised in eastern North Carolina and knew the Pamlico Sound like the back of his hand. This was an asset as he only entered and left Confederate waters at night. Since he changed his landing sites frequently, there was no way to assign a pattern to his incursions. The ship of many names spent two years dodging the union gunboats and making a fortune for the ship’s owners, a bounty they lost when the captain sailed to Bermuda where he abandoned the ship and made his way with the cash to a location unknown. The crew did not abandon the ship because they were broke. After 30 days, the time required for the company to make the situation right, the crew got a British lawyer to file for lost wages against the value of the ship and then used the money thus owed to buy the ship. In essence, the crew sold themselves the ship. The ship was renamed the Reliance because that was the name on the original ship’s papers and the crew, now owner-crew began carrying legal cargo to northern ports. Oddly, the ship made more money honestly than the company had made illegally.

There was a very good reason that the ship was so profitable. It had been running guns into the Confederacy through the Union blockade and then smuggling cotton back through the same Union blockade for four years without sustaining so much as a scratch. Just as important, the Reliance had been into and out of the roughest ports in the Caribbean dealing with arms dealers, smugglers and other rogues and had not lost a single crate to bribe, blunder or brine. The same crew that ran the gauntlet of guns-then-cotton was still onboard when the Reliance became an owner-operator which made it perfect for the next pair of shippers: the government of Spain which needed to ship arms to its navy ships and troops stretched across the Caribbean who were fighting the scattered bands of guerillas.

And the Reliance also sold arms to the guerillas.

Freedom of the Seas made the shipments doubly profitable. As long as the Reliance was three miles off shore, it could carry anything it wanted. It would lighter arms to rebels in the jungle at night and then, the next day, land at Spanish docks to offload armaments in the sunshine. Island-bouncing, the Reliance lightered-then-offloaded from one end of the Caribbean to the other and then returned to New York, Boston, Baltimore or Savannah with rum, cigars or sugar. The ship was making money coming and going.

For the next three decades, Shepherd walked the deck timbers, putting as many leagues on his boots as the ship put on the ocean. He was in and out of Baltimore, Boston, New York, Savannah and Charleston on the north end of his routes and, on the southern end, Cuba, Barbados, Haiti, Mexico, Colombia and the Antilles. Oddly, the ship did well because of its colorful past. It was well-known in shipping circles that the Reliance had been a gun runner during the American Civil War which, in those decades, was not ancient history. The history of the vessel was insignificant to prospective shippers because, as the saying went, ships do not carry cargo; crews do. The best ship in the fleet is not the newest one; it’s the one with the best crew. The crew of the Reliance was unusual because it had been together as a unit for so long. This was to be expected because they were owner-operators. They, collectively, only owned one ship and, individually, would only make money if the ship continued to sail. Thus, over the years, old crew members were replaced with sons and nephews. Shepherd, the youngest in the gun running days, became the captain in 1888. A decade later he was still there.

There were three reasons Shepherd chose to remain at sea. The first was his wife, the result of an arranged marriage, who had the face of a Cabazon, intelligence of a clam and the ardor of a lode stone. His second reason was his son, born two months after he had been married. In addition to all of his mother’s charm, Nicolas had a distaste of the sea so great he would not even go to the dock to welcome his father home. The third reason was a man he had never met, would never meet but was a pea in the maritime pod with Alonso Shepherd: Theodore Roosevelt.

Alonso Shepherd and Theodore Roosevelt did not need a crystal ball to see the future; they could smell it. It was the fragrance of profit. To leap into the future, America had to do three things at the same time: change its mishmash of ocean-going cargo and naval vessels from a jumble of wooden ships propelled by the wind to an armada of steel running on coal oil, kick Spain out of the Caribbean and build a Panama Canal. Shepherd and the crew of the Reliance knew the wood vessel’s days were numbered. It was only a matter of time before the ship would, quite literally, fall apart because of age.

Actually, it never got the chance.

Because it had been plying the waters of the Caribbean for so long and had been supplying both sides of a brush fire war between the Spanish and scattered bands of guerillas – and because the crew of the Reliance had been so successful in playing both ends against the middle – the United States Navy simply co-opted them. The Navy bought the Reliance from the crew and paid them as informers under the table. So the crew profited from the sale of their ship, had money deposited in bank accounts for being what would later be called undercover agents for the United States Navy and, at the same time, still earned wages as sailors on the Reliance and shared in the profits of each voyage because they were the ship’s owners. It was a wonderful world for the crew of the Reliance until March of 1898 when the Spanish American War broke out in earnest. At that point the Spanish government could no longer buy armaments from the United States, the United States Navy did not want the Reliance in the war zone because (it said) it was too dangerous. (But the crew of the Reliance believed) the Navy did not want the guerillas to get any more arms because the United States might well end up fighting them in a year or so. The crew was discharged and the Reliance was towed out to sea where it was set ablaze. The United States Navy was not going to spend a dime on a wood ship and did not want unsavory individuals to buy the ship at auction and use it and its reputation to continue to sell arms in the Caribbean.

Captain Alonso Shepherd took his money and ran as far as he could from his wife and son in Baltimore. That was Portland, Oregon, where he immediately found employment with the Portland Steamship and Lighterage Syndicate. The Klondike Gold Rush had just begun and the Syndicate needed maritime officers who were not going to disappear up the trail when the ship landed in Skagway. Shepherd was perfect for the job. He had four decades of experience at sea, did not need the money, was cargo purblind and, most important as it turned out, he began a tumultuous love affair with a spinster aunt of one of the board members. The aunt controlled 15% of the voting stock and seeing Shepherd for a week a month was a gift of the gods to the Syndicate for it was during that week that they held their monthly board meetings. The half of the year when the mantle of the Bering Sea was frozen from Siberia to Alaska, Shepherd captained the Bella Ann from Portland to Maui and thence to San Francisco and back to Portland – and for half of that half-year, the aunt came with him as well.

Shepherd and the Syndicate were a perfect fit. Shepherd was an old sea dog who was still strong enough to spend another decade at sea. Shepherd wanted to spend another decade at sea, this time on a steel ship powered by coal and had two very good reasons not to want to return to the East Coast. The Syndicate saw in Shepherd the future of the Syndicate. Theodore Roosevelt had just funded a sort-of, kind-of revolution in Colombia that created the nation of Panama which immediately leased the United States what became known as the Canal Zone. This meant the Panama Canal was going to be built with American know-how – and that meant success. Further, the American Navy was grabbing every island it could in the Pacific Ocean. These bare, desolate, lonely and uninhabited fly specks in the middle of nowhere were going to be the fuel dumps of the future, fuel dumps that companies like the Portland Steamship and Lighterage Syndicate could use to sell American products to Southeast Asia and bring products from the eastern shore of the Pacific Rim to the West Coast of the United States.

Better yet, with the opening of the Panama Canal, the cost of East Coast goods to the American West Coast was expected to drop by half. Cheaper American products on the West Coast meant more profit for the Syndicate in Southeast Asia. So the Syndicate was positioning itself to be in the right place at the right time. All Shepherd had to do was continue the Alaska run until the Panama Canal opened. After that, who knew what riches lay in wait for the prepared?

Thus was Alonso Shepherd, a man used to sizzling under a tropical sun and dealing with shadowy arms merchant, found himself the master of milk runs to Alaska and Hawaii. But be the seawater warm or cold, he found that merchants the same. They had ice water for blood and shaving the corners for a few cents of profit was same the whole world over. He knew that 95 percent of his cargo was legitimate. That left a few tons of crates that were mislabeled. He didn’t care. He wasn’t a partner in this venture and if the Syndicate signed off on the crates, who was he to look for trouble where there was none?

But what intrigued him was not the incoming cargo. It was the outgoing. The Steamboat Inspection Service was always interested in what was going from the lower states to Alaska but it could have given a hang nail for the incoming cargo from Alaska. After all, what could possibly be coming in from Alaska that might be contraband? So inspector after inspector looked at the incoming manifests and kicked them into the high grass. If the Steamboat Inspection Service didn’t search the hold and the Syndicate didn’t care what was coming and going on their vessel, why should Shepherd?

So he didn’t. Cargo on its way to Mexico went on its way. Crates about the size of a suitcase. Two or three per trip all summer and fall in the Year of the Steamship and the Year of the Post Office. Whatever it was it went south without a hitch. No one complained so no one was concerned.