Battle of San Diego Bay

Smugglers cruise into the harbor

Rodriguez was convinced that Presidio Hill, overlooking a river and two bays, was the most windswept promontory in creation.
  • Rodriguez was convinced that Presidio Hill, overlooking a river and two bays, was the most windswept promontory in creation.

Another Boston trader anchored in the bay? That’s four in the last three years. What is this, a plague?

And the captain will need wood, provisions. Or his ship may have sprung a leak and must remain in the bay to refit. All the while the crew will sneak off and trade for sea otter pelts with the padres and Indians. Then the ship will sail to Canton, where it will sell the pelts, the “royal fur of China,” for a king’s ransom in porcelain, silks, carved chests, and quicksilver.

Between 1800 and 1803, Lt. Manuel Rodriguez, commandant of the San Diego Presidio, heard that story four times. He also witnessed a slow transition: a flea-infested, forlorn outpost promised wealth — from the pelts of sea otters — if the smugglers could linger long enough to make contacts on shore. Historians claim the first years of the 19th Century in San Diego were relatively peaceful. Ask Lt. Rodriguez, who earned 550 pesos a year trying to maintain a precarious order, and he’d swear he was cursed to live in interesting times.

Son of a wealthy merchant family, Rodriguez came to California in 1795 as a cadet, a “gentleman obliged to live on soldier’s pay,” sponsored by his uncle Carcaba. He rose quickly in the ranks, serving as acting commandant of the San Diego Presidio from August 23, 1799, to early 1803, when he became commandant, at age 37. During those years he tried to rebuild the dilapidated presidio. Letters to Governor Arrillaga in Loreto complain that fortifications were crumbling, that an earthquake — on November 22, 1800 — cracked several buildings, including the warehouse.

Rodriguez was convinced that Presidio Hill, overlooking a river and two bays, was the most windswept promontory in creation. Constant gusts lashed the west-facing walls and hurtled roof tiles across the square. These smashed into the church, or the cemetery, near the east wall, or into anyone happening to be out and about.

In a letter to Arrillaga, January 13, 1802, Rodriguez admits giving up on restoration. Adobe was eroding, timber crumbling: “Daily repairs are made to this presidio due to the circumstances of its poor location and being the oldest of all such establishments.” He demanded a new one, built somewhere else — anywhere, as long as it was closer to water and wood and on much flatter ground. He also requested “professors of the art” to do the job, since the local architect, who never ordered enough adobe or lumber, had no idea where to start.

By 1803, almost 200 people lived in the compound. An open square — 300 feet to a side — with buildings at the walls, the presidio was roughly the size of a large city block. One or two dwellings had been built out- side by then, but it wasn’t until the early 1820s that people moved down to what would become Old Town.

California presidios were the equivalent of exile for a soldier. Of the 60 soldiers here at San Diego, 13 were “invalidos,” unable to work. Some were wounded but most were retirees who had served two six-to eight-year hitches and lived on pensions that would make today’s military envious.

One class of soldiers, the distinguidos, would not work at all. Distinguished for bravery, they were exempt not just from petty labor but even from physical punishment. Those soldiers who could, refused to work on the presidio itself. The labor was too intense, the pay too low. Complained Corporal Periquez: “Slaves could not have been treated worse.”

Mission Indians did much of the work, for a pittance they had to share with the padres. Unbaptized Indians also worked for low wages. This ranged from bringing water from the river in clay pots and leather buckets — like hauling stones up a mountain — to manual repair of the buildings.

Added to problems of grumbling soldiers and understandably irate natives, Rodriguez’s command was subject to two forms of discipline: military (always difficult to enforce) and religious. The brown-clad friars chosen to build missions in Nueva California were “Observants,” the most strict of the Franciscan order. From Father Serra down, they embraced hard- ship. Anything that tormented the flesh brought them closer to God. In their eyes, military discipline was not severe enough. “San Diego got good commanders,” says historian Jack Williams,“because they were needed. In 1800, San Diego was frontier, a no-man’s-land. Nothing was secure. The Spanish controlled only small parts — and would be ambushed if they ventured beyond them. Even the path from the presidio to the anchorage near Cobblestone Point, much of which was marshland, could be a danger zone.” When George Vancouver visited in 1794, he found San Diego desolate, poorly defended, “the least of the Spanish establishments.” His boat had anchored just east of Punta de Guijarros (“Cobblestone Point”; today’s Ballast Point). A fort built at the base of Guijarros, he said, would render San Diego “a place of considerable strength.”

Under Rodriguez’s direction, work began on the fortified structure in 1797. Indian labor mixed mud and straw for thick adobe walls, on the seaward side. Lumber came from Monterey, tiles from San Luis Rey. By 1800, the fort had between six and ten cannons facing the channel. One, a bronze nine-pounder from Manila, was nicknamed “El Jupiter.”

Beginning in 1800, four “trading” ships from Boston sailed past the small fort and anchored east of Ballast Point in ten fathoms of water. In 1803, El Jupiter was fired in anger at the fourth ship.

The first ship rounded Point Loma on August 25, 1800. Tall masts and billowing white sails were such a rare sight that many in the presidio rode to Guijarros to take a better look. A Boston brigantine — 65 feet long, 104 tons, a female figurehead, and a crew of 19 — the Betsy was the first American ship to enter San Diego Bay. Its captain, Charles Winship, exchanged formal military bows with Rodriguez.

Winship said he’d been to Hawaii — which he pronounced “oh-why-hee” — and the north. He was headed for China but needed wood and water. Winship, his supercargo (the ship’s business agent) Joseph O’Cain, and first mate John Brown negotiated with Rodriguez. Though under orders not to permit foreign trade on Spanish soil, Rodriguez followed international maritime law. He’d supply wood and water, and the crew could come ashore — but only to exercise at the beach. They couldn’t visit the presidio or fraternize with local inhabitants.

The Betsy remained in San Diego harbor for ten days. Rodriguez supplied its needs. After cordial farewells, the ship sailed, allegedly for China.

The second Boston ship, the Enterprise, arrived June 28, 1801. During the interim, Rodriguez had been alerted that the Boston traders might be smugglers. They would come ashore, on some excuse, and deal for furs on the sly.

At 240 tons, a crew of 21, and 10 cannons protruding from its sides, the Enterprise was a formidable sight. The captain, a crusty old sea dog named Ezekiel Hubbell, told Rodriguez he couldn’t continue his voyage to China without bread and other foodstuffs. Could he and his crew come ashore? Yes, said Rodriguez, but only to pick up supplies brought to the ship. To make sure, Rodriguez stationed an ensign onshore, near the anchorage, to watch all movements.

Between June 28 and July 3, the skiffs and jolly- boat — a yawl-like sailboat — from the Enterprise made frequent trips. They waved a flag to assure the guard they were only hauling supplies. After taking in six cattle, several pounds of flour, beans, corn, and salt, Captain Hubbell saluted Rodriguez with a flourish and sailed away.

Two potential smugglers in a year: Rodriguez must have felt like a father protecting his daughter’s virtue. William Smythe: “If either of these earliest American captains succeeded in doing any illicit trade in San Diego, they kept the secret successfully, leaving not so much as a rumor of scandal behind them. Such was not the case with those who came shortly after.”

The skipper of the third ship, the Alexander, looked familiar. He was John Brown, first mate on the Betsy. As Rodriguez was to learn later, therein hung a tale.

Instead of sailing to China, after leaving San Diego the Betsy went south, cruising the lower California coast for furs. In a letter to his brother in Boston, Captain Winship boasted that he’d been stopping in Spanish ports, hoodwinking authorities, and trading for furs with California Indians. He’d exchange trinkets or blue-colored cloth for a pelt worth up to $80 in China (a dollar in 1803 equals $12 today; thus each pelt earned close to $1000). When it reached San Blas, the Betsy’s hold was almost full.

To buy time to trade at San Blas, Winship told port officials a northern storm had cracked the ship’s main mast. He must repair it in a protected bay. While the ship was staying at San Blas, however, two Spanish vessels arrived. John Brown took the helm. The Betsy pulled up anchor, unfurled sails, and raced out to sea — leaving Captain Winship and Joseph O’Cain on the beach. Instead of coming back for them later, Brown sailed with the precious cargo to China.

Necessity? Mutiny? In later testimony Brown claimed he fled so that the Spanish ships couldn’t seize the pelts. O’Cain argued mutiny and demanded — unsuccessfully — his share of the profits. Winship had no say. He died of sunstroke at San Blas, December 4, 1800. He was 23.

Among Winship’s possessions, Spanish authorities found the letter to his brother, bragging about his smuggling activities. All ports along the California coast got a warning: Winship had been “hiding the truth in his declaration” of need. Other Boston traders might be as well.

When the 67-foot, 14-gun Enterprise entered San Diego Bay at sunset, February 26, 1803, Rodriguez recognized its captain, John Brown. Though he was prepared to hear tales of woe, Rodriguez wasn’t ready for this one. Brown presented the frigate’s papers to Rodriguez. Then, in a melodramatic gush, Brown blurted out that 9 of his 19 men had scurvy. If they couldn’t convalesce on land, they’d surely die.

Rodriguez was torn. Duty said ‘Sail off ’; compassion said otherwise. The stricken crew members could come ashore for eight days, he decided, but only to an isolated spot far from the presidio. They would receive wood, water, beef, and fresh vegetables. The rest of the crew must remain aboard the Alexander. There weren’t enough Spanish soldiers with him that night, but in the morning Rodriguez would post a six-man guard on the ship. They would keep watch, inspecting every rowboat.

After five quiet days, Rodriguez became suspicious. He and four soldiers rowed to the Alexander and conducted a search. In a storeroom next to the main mast, a soldier found stacks of furs, piled to the ceiling.

“Contraband!” Rodriguez declared. He ordered his soldiers to toss them onto the deck. By the official count, 491 otter pelts flew out the storeroom door. The commandant took them to the presidio and locked them in the warehouse. He also demanded that the Alexander leave at once.

How did the skins get onboard? Was Rodriguez’s six-man guard in collusion with Captain Brown? Were the nine sailors on shore less “isolated” — and less stricken with scurvy — than they seemed? Their bonfire could have been a beacon for friars and Indians eager to trade. Wanting to believe the best, and protecting his reputation as a leader, Rodriguez wrote that the contraband must have come aboard that first night, when he couldn’t post a guard on the ship.

A partial answer comes from letters written to Governor Arrillaga shortly after the Alexander affair. A friar from San Luis Rey requested the 170 pelts a mission Indian sold to the Bostonians. This was the first evidence that some padres were in league with the traders.

In the second letter, Corporal Onofre Villaoa demanded either the return of 223 furs he “pretended” to sell to the frigate or double their value (“conque le cobron dobles”) in goods or cash.

Neither got his wish. The case went to court. It remained unresolved so long that the furs began to rot, the stench creeping through cracks in the warehouse. By the time a ruling had been made, the pelts had decayed so badly they stunk up the entire presidio. Rodriguez ordered them dumped in the bay.

Magdalen Coughlin: The fur trade grew because “the people wanted the things Spanish sources simply were not supplying. Also, California was the farthest removed from the seat of authority in Mexico, affording an opportunity for officials to supplement considerably their meager salaries. Without either adequate coastal patrol or presidial garrisons, what could an official’s attitude be but “¿quien sabe?’ ” — who knows? “It was like fighting a plague with a fly swatter.”

Rodriguez had become wary of foreign ships and allies: who knows where a friar or a soldier might stand? And now, just two weeks after the Alexander fled the bay, another Boston brigantine has anchored near

Guijarros? That’s the fourth in three years! What is this?


  1. Bancroft, Hubert Howe, The Works of Hubert Howe Bancroft, vol. xix (Santa Barbara, 1966)
  2. Cited letters come from the “Provincial State Papers” (Spanish transcripts at the Bancroft Library), vol. XII and XVIII; also from Provincias Internas, vol. XVIII, no. 1
  3. Coughlin, Magdalen, C.S.J., “Boston Smugglers on the Coast (1797–1821): An Insight into the American Acquisition of California,” California Historical Society Quarterly 46 (June 1967)
  4. Miller, Max, Harbor in the Sun (New York, 1940)
  5. Ogden, Adele, The California Sea Otter Trade, 1784–1848 (Berkeley, 1941)
  6. Pourade, Richard, The Time of the Bells: When California Began (San Diego, 1961)
  7. “Report of Corporal Periquez to Captain Callis,” Writings of Junípero Serra (Washington, D.C., 1966)
  8. Smythe, William, The History of San Diego, vol. i (San Diego, 1907) 9. Williams, Jack, San Diego historian-archaeologist, interview


  1. Adele Ogden: “The commercial opening of the Pacific Ocean was begun because of man’s desire for the fur of an animal.”
  2. Max Miller: “The Spaniards would have preferred that there were no otters. The otters were serving as a floating advertisement, bringing more and more foreign vessels which otherwise would have stayed away.”
  3. Sullivan Dorr, of Dorr Shipping, on American smugglers distrusting each other: “There is ample field for villainy here.

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