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The Origins of San Quentin Prison

San Quentin Prison, which stands on a point of land just south of the Marin side of the Richmond-San Rafael Bridge, is the oldest prison in California and one of the most famous in the country. Today San Quentin subscribes to the tenets of modern penology, which emphases rehabilitation and discourages the harsh treatment of inmates. But that was far from the case during its early years. The story of San Quentin’s origin is one of the stranger tales in the annals of California.

The prison’s story begins in 1849, when San Franciscans, fed up with the thuggish behavior of a group of rogue Mexican War vets who called themselves the Hounds, organized themselves into a posse, arrested the band’s leaders and sentenced two of them to long terms in the penitentiary.

There was only one problem: There was no penitentiary. San Francisco’s only lockup was a “calaboose,” a log structure so feeble that a prisoner once showed up at the alcalde’s office with the jail’s door on his back, threatening to leave if his breakfast was not served. Unable to imprison the Hounds, the law-abiding citizens were forced to exile them.

This situation led city authorities to purchase a brig, the Euphemia, to use as a prison ship (it doubled as an insane asylum). Prisoners on the Euphemia were sent ashore on a chain gang to do public works.

As crime increased, the need for a state prison became more pressing. In 1851, a leading Californio, Mariano Guadalupe Vallejo, and his partner, a Democratic politician named James Estell, offered the state what looked like a sweetheart deal. Vallejo and Estell proposed to give the state 20 acres of land, build a state prison on it, and operate it themselves. As Kenneth Lamott writes in “Chronicles of San Quentin: The Biography of a Prison,” until they built the prison, “Vallejo and Estell promised to buy prison hulks, hire and pay the officers and guards, clothe and feed the convicts, and offer rewards should they escape. As their quid pro quo, they asked only to be given a free hand in putting the convicts’ labor to any use they wished.” In other words, they wanted to run the state prison as a for-profit business, using the convicts as quasi-

slave labor. Unsavory as this approach was, it was not uncommon at the time, particularly in the South: States that leased their prisons to private businessmen included Kentucky, Texas, Missouri, Alabama and Louisiana.

The California state legislature, after discovering that states that ran their own prisons operated at an average annual deficit of $100,000 a year, eagerly accepted the offer.

On April 25, 1851, Vallejo and Estell formally leased for 10 years the labor of California’s state convicts — who at the time numbered exactly five. This was the inauspicious beginning of California’s state prison system.

allejo and Estell were a peculiar duo. Vallejo was a prominent Californio general, ruthless Indian fighter, and rancher who famously supported the American takeover of California. Estell was, in the words of Lamott, a “notable scoundrel … an adventurer and politician by trade, a man of some ability, but his mind was wild and injudicious and his tongue was one of the foulest ever heard in a public hall.” The San Francisco Bulletin, which detested Estell, described his “hideous face and Cain-branded countenance” and predicted he would go down in infamy as the vilest of the vile.

Estell and Vallejo subleased custody of the convicts to the sheriff of San Francisco, a dashing former Texas Ranger named Col. Jack Hays, and his friend Major John Caperton. From the hundreds of derelict ships abandoned in the bay, Hays and Caperton acquired an old bark named the Waban, fitted it out as a prison ship, and loaded it with 40 convicts. On Dec. 18, 1851, the steam tug Firefly towed the Waban across the bay to Angel Island. The prisoners were put to work in a quarry during the day, returning at night to sleep in cells on the Waban. Other prisoners, those considered less likely to escape, were imprisoned in the unfinished and insecure county jail on Broadway in San Francisco, from where they were driven out in chains to work on the streets.

The prisoners on the Waban labored under the supervision of one John McDougal, who seven months previously had been the governor of California. Described by Lamott as “An unsuccessful miner turned politician, a buffoon, and a drunkard,” McDougal issued so many bombastic proclamations beginning with the words “I, John McDougal” that he became universally known as “I, John.”

Hays and Caperton’s foray into the prison-labor business turned out to be a disaster. Hays had been a cavalry hero in the Mexican War, but he proved to be a less than impressive jailer. A month after he took command 17 of the 40-odd prisoners on the hulk locked up their three guards, took their weapons, commandeered a boat, and took off for the East Bay. Hays led a chase, but seven convicts got away.

Hays and Caperton’s venture also proved financially ruinous: within five months, they had lost $11,000 of their own money. Hays asked Estell to take the convicts back, but Estell refused. Vallejo had dropped out as a partner, ending one of the less glorious chapters in his storied life. Estell finally agreed to release Hays and Caperton from their sublease, on the condition that the legislature approve construction of a state prison. On May 1, 1852, the legislature passed an act authorizing the purchase of 20 acres of land for that purpose.

Point Quentin, the spit of land where San Quentin stands, was not the state’s first choice. Angel Island, Alcatraz and Goat Island (Yerba Buena Island) were the favored sites, but land-title problems led commissioners to choose Point Quentin. On July 14, 1852 (fittingly, Bastille Day), the Waban (which had been moved to Goat Island), with its 40 to 50 convicts, was towed across the bay to Point Quentin.

The convicts were sent out during the day to work on the prison site, then locked up below decks at night. Confinement on the Waban was a cruel and unusual form of punishment. Four or five men were squeezed into each 8-foot-square compartment. “During the warm summer days they stewed in their own juices, while in the rainy winter they stayed below day after dreary day,” Lamott writes. “In the mornings the effluvia of feces and sweat and general decay was so strong that the guards refused to go below until the lower decks had been aired out.”

Meanwhile, the walls of San Quentin’s first cell block, which became known as the Old Prison, the Stone Building, or simply the Stones, were going up. But the new prison proved to be just as chaotic and mismanaged as the old brig, replete with sexual shenanigans, frequent escapes, official corruption, laughably lenient treatment of favored prisoners and vicious floggings handed out for offenses serious and trivial alike. That story will be the subject of the next Portals.

(SF Examiner)

One Comment

  1. Luckie cruz May 8, 2023

    I lived at San Quentin from 99 to 2002 it was no joke. Paked stabbings a couple time a week shower backed up with disgusting filthy water I took a bird bath in my cell and washed my clothes in a five gallon bucket for 3 years that fucking dump needs to be bulldozed

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