1915 Sq Paddle Wheel Steamer At Prison Dock

The paddlewheel steamer Caroline brought supplies to San Quentin State Prison and took away prisoner-made jute bags. At one time, the ship was used to transport convicts from San Francisco to the prison. The ship’s captain helped find work for parolees, circa 1915. Courtesy Anne T. Kent California Room, Marin Public Library.

By Don Chaddock, Inside CDCR editor

(Editor’s Note: Much like today’s corrections department, early efforts were made to reform offenders and help ease their transition to society. With San Quentin sitting on the Bay, ships were a regular sight for those working the docks at the prison. Even after the state moved on from maintaining its own small fleet of ships, sea-going vessels still played a role in the rehabilitation of offenders. This is the final installment of a four-part series examining the state prison system’s maritime history.)

Inmates who learned job skills at the prison often had difficulty landing employment post-release. Luckily, they found an eager ally in a grizzled sea captain who had delivered supplies as well as inmates to the prison for decades – he usually staffed his ship with former offenders.

1912 Capt Leale Steamboat Caroline Employed Exconvicts

In a 1912 Sunset Magazine feature, Capt. William Leale discussed hiring ex-offenders.

“Under command of Capt. William T. Leale, the Caroline plied between San Francisco and San Quentin for years, carrying stores for the inmates of the prison,” reported The American Marine Engineer, March 1918. “Capt. Leale, until his retirement when he tied up the Caroline annually, put the little bay steamer into the dry dock for overhauling and painting, and then he gave an outing to his newspaper friends of the bay cities.”

His passengers had no idea the crew had once done time in the state prison.

“Her crew for the most part was composed of ex-convicts, but none knew this except her kind-hearted captain and owner, Capt. Leale, who believed that every man had a regaining quality when put upon his honor. For many years, Capt. Leale made it a point to employ none but discharged convicts from San Quentin as members of the crew of the Caroline. The Caroline was always well supplied with good food and her skipper gave good advice to his crew. More than that, he sent them out into the world with a new lease of life.”

Leale had also transported inmates for years as part of a contract with the state prison.

In 1911, Capt. Leale volunteered to shuttle actors, props and equipment, as well as some audience members, back and forth to the prison for its first-ever stage production by an outside theatrical company. (Editor’s Note: See next week’s Unlocking History installment on the play and its influence on arts as a rehabilitative tool.)

The captain had a well-earned reputation for giving former offenders a chance. Six years earlier, he was featured in Sunset Magazine, November 1912. According to the magazine article, the captain was 68 years old.

“It was in the midst of the cantaloupe season, and the market in San Francisco was glutted,” the magazine reported. “On Jackson-street wharf, 200 crates of cantaloupe were piled and since there was no market for them, they could not be sold. Since they were perishable goods, they could not be returned to the farmer who shipped them. Since the consignee refused to accept them and move them off the wharf, the chief warfinger had ordered that the entire 200 crates be dumped overboard.”

After they began dumping, Capt. Leale confronted them.

“He demanded to know why in blue blazes 200 crates of perfectly good cantaloupe should be consigned to the fishes when 1,800 poor devils up in the penitentiary at San Quentin were ready and willing to eat them,” the magazine reported.

1903 William Leale Photo

William Leale, 1903.

“I can haul the Caroline alongside, and I’ll relieve you of those crates of cantaloupe in about two shakes of a lamb’s tail,” Capt. Leale told them.

According to the story, “Capt. Leale’s specialty is the Submerged Tenth. It’s a habit. He can’t help it. That’s his nature and it’s the marvel of the San Francisco waterfront how the earnings of the Caroline … manage to stand the strain of this salt water philanthropist.”

The Submerged Tenth refers to those who are chronically impoverished.

The captain was very familiar with the prison and its inmates.

“The Caroline, with Leale at her helm, has been carrying miscellaneous freight up to the state prison at San Quentin for the last 30 years. On her return trips, she has carried jute gunnysacks. Few people realize that in the harvest season, the fate of the California farmer hinges on Bill Leale and the Caroline,” the magazine reported. “The most hardened criminal has a smile and a good word for the skipper when the old Caroline makes up to the dock at San Quentin.”

Leale treated the inmates as men with names rather than numbers.

“While the men in stripes discharge the Caroline, the skipper walks among them, talks to them, gets to know them and their sad secrets,” according to the story. “The skipper watches his convict friends, talks with them, notices whether they handle freight like men who work from choice or from necessity.”

Sq Wagon Manufactory, State Prison, 1870s Crop

Inmates build wagons in San Quentin, circa 1870s. They also worked on board ships and learned other trades and skills.

If the skipper was pleased with their work ethic, “he goes after a parole for that man. It has often taken the skipper years to get the parole, but he gets it. … He puts a (bug) in the warden’s ear, or the governor’s ear, and he assaults the combined ears of the State Board of Prison Directors and (since) everybody loves him and class him ‘Cap,’ what are they going to do about it?”

Back then, for a prisoner to be paroled, he had to show he had a job waiting for him outside the gates.

“‘Well, how about his job?’ (they ask). ‘He’s got a job,’ retorts the skipper. ‘Where?’ (they ask). ‘Deckhand on the Caroline,’ (the skipper responds).”

According to Sunset Magazine, the ship carried quite a few ex-convicts.

“But that’s Capt. Leale. He’s never happy unless half his crew are ex-felons. He will tell you that 90 percent of them make good. He puts them on their honor, after he’s given them that job they need so badly in order to be paroled,” the magazine reported. “When a convict that the skipped knows for a ‘pretty decent fellow’ comes out of ‘stir’ with a suit of the cheap prison-made ‘free’ clothes that shout his shame to all the world, it is Capt. Leale who takes him in tow, leads him to a clothing store and stakes him to a suit of store clothes that will hide his history. Next he goes after a job for that man. Stewards, waiters, deckhands, freight clerks on the river and bay steamers – lots of these are Leale’s proteges. He even scattered some of his Submerged Tenth on farms up and down the San Joaquin (river) and the Sacramento.”

He also showed his appreciation to the staff at the prison.

“Every May-day, the children and wives of the guards and officials at San Quentin are his guests for an all-day cruise around San Francisco Bay. He has on his free list, also, a few orphan asylums and charitable organization whose specialty is children. He gets his fun watching other people wax happy, particularly children and the Submerged Tenth.”

The magazine’s profile on Leale describes him as a real character, quick of wit and “rich in sea yarns and humorous anecdote.”

“He is a jolly old sea-dog, a mimic, a monologist, a rare raconteur and all-around entertainer,” the magazine reported. “He might have won a place for himself on the vaudeville stage, but he would rather stay at home and jolly his friends and money with problems in social economy. A thousand (dollars) a day wouldn’t bring the skipper away from San Francisco and the Caroline. She’s a good old craft, for all her years, and Bill Leale loves her. They have worked together so many years that they understand each other.”

Leale lost his wife Lily in 1915. He lost his other great love, the Caroline, just three years later.

“Last month, the old stern-wheeler Caroline succumbed to the ravages of fire and sank at her anchorage of Sausalito. The origin of the fire is unknown as there was no one on board,” reported The American Marine Engineer, March 1918.

Later that same year, Leale died and was buried alongside his wife in an Oakland cemetery.

With the evolution of transportation methods, offender rehabilitation efforts also evolved. By 1920, the automobile had become popular and a major effort was put into building a network of reliable roads. Inmate crews were some of the first to build those roads in rough, steep terrain. Later, many of those road camps converted to harvest camps and eventually fire camps, which are still in use today.

1915 Sq Horse Team At Prison Dock

A horse team is loaded at the prison dock, ready to bring the supplies inside the prison, 1915. Inmates loaded and unloaded the ships. Courtesy Anne T. Kent California Room, Marin Public Library.