Sunnyside/Jailside: the tale of the big house down the street

By Amy O’Hair

Who would site “the Largest and Most Important City Subdivision” next to an extensive and notorious jail compound? That’s exactly what Behrend Joost did in 1890 when he created the Sunnyside district from a portion of the Rancho San Miguel land that Leland Stanford sold off then. The choicer cuts went to other investors; this was no Stanford Heights (later Miraloma Park), perched on Mt Davidson. (Joost’s true aim was to be Baron of the Electric Rails, in any case.)

Half-page debut ad for Sunnyside, altered! SF Chronicle, 26 Apr 1891. Click for larger.

There had been a jail on this property in some form or another since the 1850s; the city originally bought the 100-acre House of Refuge lot in 1854, when it was far, far from the city. The 1905 view show below is now unimaginable: the Jail complex has been replaced by City College of San Francisco, and the narrow railroad tracks of the San Francisco-San Jose train line that passed directly by have been replaced by the Interstate 280 Freeway.

1905. View of Ingleside Jail from Ocean Avenue, looking northwest. Southern Pacific tracks run just below jail's white fence. Courtesy SFMTA. Cropped from U00341.
1905. View of Ingleside Jail complex (women’s on left, men’s on right). Looking northwest from Ocean Ave near San Jose Ave. Southern Pacific tracks run just below jail’s white fence. Courtesy SFMTA. Cropped from U00341.

1869 Coast Survey map, altered: House of Refuge lot marked in green. From
1869 Coast Survey map, altered: House of Refuge lot marked in green. Click for larger. From

The Jail was Sunnyside’s close neighbor; the high white fences on the northeastern side touched Havelock Street, Sunnyside’s southernmost street. The compound had different names and reformatory functions over the years: House of Refuge; Industrial School; House of Correction; Branch County Jail No. 2; and finally Ingleside Jail, after 1906.

1922 aerial photo, cropped, altered, and colored. Ingleside Jail complex at center left. Click for larger. (Original photo:
1922 aerial photo, cropped, altered, and colored. Ingleside Jail complex at center left. Click for larger.  (Original photo: OpenSFHistory wnp27.0542.jpg)
2017 OpenStreetMap, altered to show locations of men’s jail (purple) and women’s jail (pink). Click for larger
1938 aerial photo, altered to show location men's jail (purple) and womens' jail (pink) shortly after buildings demolished. From Click for larger image.
1938 aerial photo, altered to show location men’s jail (purple) and womens’ jail (pink) shortly after buildings demolished. From Click for larger.

At all points in its history it was in theory supposed to house only those inmates who: had short sentences; were not guilty of federal crimes; were thought reformable. In fact it turned out to be an appealing alternative for San Francisco convicts who had enough money to bribe their way into serving their sentence at “The Sheriff’s Ranch,” as the jail was known(1), thus avoiding the dreaded fate of the much harsher state prisons like Folsom. As a result, it put alimony-scofflaws in beside murderers, and was always an excellent place to learn the finer points of the illegal trades.

Anyone living or walking on the southern streets of Sunnyside could see its battered fences and the tops of its grim structures. And so it was, from the time the streets were laid out in 1891 until 1934, when the jail inmates were finally moved to a new building in San Bruno—forty-three years of co-existence. Perhaps it added a certain frisson to living in the “sticks,” as the neighborhood was still called, even as late as the 1920s.(2)

A Village unto Itself

It was an establishment isolated from the city that frequently found its way into the news, with good reason. It was rife with free-flowing drugs and alcohol, administrative corruption, drunken guards, and a history of prisoners escaping through its flimsy wooden fence. One Sunnysider who lived as a child at Foerster Street and Flood Ave told in an oral history of how the alarms would go off at the Jail and that would mean the kids were supposed to run home right away because a prisoner had escaped.(2)

The complex in 1891 encompassed two separate jails, for men and women. In these years it held between 300 and 400 inmates, plus all the staff and administration workers and their families. In 1910 the census reveals that there were 350 inmates, 27 administration and staff workers, two wives, and eleven children, all living on site.(3)

1910s. View of Ingleside Jail looking west from the site of the current Ingleside Police Station, on Sgt John V Young Lane.
1910s. View of Ingleside Jail looking west from the site of the current Ingleside Police Station, on Sgt John V Young Lane.

The women were housed in a rather derelict building that was the original 1858 House of Refuge (an early juvenile detention facility). Half of it fell down in 1906 Quake, but they continued to use it until it was closed and the women transferred to a new women’s jail behind the Hall of Justice downtown on Portsmouth Square in 1930.(4)

The men had a newer and bigger building, built in 1876, considered the height of enlightened practices at the time. The two larger wings held the inmates, the smaller one was residences for the administration and other staff. There was a central octagonal hall.

The grounds and outbuildings were extensive; there were farm animals and vegetable gardens; a well and large water tank; a large kitchen; a laundry; construction and shop facilities.

Matron's house at Ingleside women's jail. OpenSFHsistory WNP36.00948
Matron’s house at Ingleside women’s jail. OpenSFHsistory WNP36.00948

The compound was all encompassed by a 16-foot wooden board fence, installed when the building was constructed. It was an infamous feature of the jail, as it proved an insufficient deterrent for various determined escapees armed with small saws over the decades, as well as blowing over in strong storms. At frequent intervals from the 1880s to the 1920s, the Board of Supervisors or the Grand Jury called for it to be replaced with brick or stone, but it never was.

Jack Black: Out the Front Door and through the Streets of Sunnyside

One of the most publicized escapes from Ingleside Jail was Jack Black, who made his exit from the compound in January 1912, in the last days before Sheriff Tom Finn turned over the keys to his elected replacement, Frederick Eggers. Black was one of the reformatory projects of Fremont Older, editor of the Bulletin, but even Older’s efforts at intervention couldn’t save Black from being made to serve his 25-year sentence at Folsom State Prison. (Read an SF Call account of the spring 1904 ‘Mission Bandit crime spree that put him inside.)

Jack Black and Harry Davenport escape Ingleside Jail. SF Call, 5 Jan 1912. Click for larger.
Jack Black and Harry Davenport escape Ingleside Jail. SF Call, 5 Jan 1912.

Black had resided at Ingleside Jail since 1906, moved there with all the inmates from the Broadway Jail, which burned down in the Great Fire. Many prisoners waited years at Ingleside while lawyers wrangled over restoration of police records, all burned in the Fire. When he left in 1912, he was on the verge of finally being sent to Folsom, his expensive lawyers and connected friends having failed at preventing it.

Enterprising as always, he had made a small fortune during his years at Ingleside, and left the jail with a money belt full of cash, $3000 ($76K now) and “a suit of the finest cloth and latest cut.”(5) It was reported that he won much of it gambling with Abe Ruef during the Boss’s stay at the jail. This seems a bit unlikely, as Ruef was only there for two fairly brief periods, in 1908 and 1911.

In his memoir 1926 You Can’t Win, Black recalls his time at Ingleside Jail:

“Money was plentiful in the jail. The grocer came every day and we all got enough to eat. The political boss [Ruef] bought many books and founded a library. He also got a big phonograph that was kept going all day and far in to the night. I was ‘appointed’ jail librarian, and at once catalogued the books and installed them in an empty cell. The jail was a cross between a political headquarters and an industrial plant. The political prisoners [there were also supervisors inside on graft charges] did politics and the prisoners whose records were burned in the fire turned to industry. We got contracts to address envelopes and sublet the work to others. We sewed beads on ‘genuine’ Indian moccasins for a concern downtown. Best of all, we bought cheap jewelry from mail-order houses and sold it at a profit to visitors, giving them to understand that it was stolen stuff we had smuggled in with us.”(6)

The way Black made that money was more like the drug-delivery operation that he conducted during the course of his stay. A famous dope-addict himself—his memoir was deeply influential for the teenaged William Burroughs—he injected other inmates through the bars of his cell and collected his fees. The whole story came out in the months of investigation that followed his escape.(7)

The escape happened after midnight on 5 Jan 1912. Stories about how he and Davenport got out were varied and speculative. One of the only witness reports revealed that at 1 am, two owl-car drivers on the 10 Sunnyside streetcar line spotted two men waiting near a large saloon auto at the corner of Edna Street and Sunnyside Ave (now Monterey Blvd).(8) “At the edge of the Sutro Forest” was how the location of the rendezvous point was described.

1922 aerial photo altered to show the route Jack Black took from the jail to the waiting car which would whisk him and Davenport away to freedom. Original image:
1922 aerial photo altered to show the route Jack Black took from the jail to the waiting car which would whisk him and Davenport away to freedom. Click for larger.  Original image: OpenSFHistory wnp27.0542.jpg
1917 photo showing Monterey Blvd near Edna Street (streetcar track being re-laid). Spot where get-away car seen marked with purple dot. Cropped from photo U05832 courtesy SFMTA:
1917 photo showing Monterey Blvd near Edna Street (streetcar track being re-laid). Spot where get-away car seen marked with purple dot. Cropped from photo U05832 courtesy SFMTA:

Soon, the witnesses said, another man, ailing and weak, came up and was bundled into a blanket and put inside the automobile. That man was probably Black; he later described his escape:

“Strange as it may sound, the fresh cool night air had the same effect on me that the foul air of a sewer would have on a healthy, normal human. It overcame me. I was not able to walk at first, and my rescuer had to support me on our way to the car line.”(9)

Black maintained silence to the end about how he got free, thieves’ honor still counting for something; he insisted in his memoir he took the streetcar, rather than reveal that there was a third person helping him and Davenport with an automobile.

Black and his compatriot Davenport got away clean. Black was recaptured in Vancouver in November of that year and after some difficulties about extradition, returned to SF.(10) Davenport wasn’t recaptured until 1918, in Missouri.(11)

Again, Fremont Older intervened for Black, and ultimately Black served only one year of his 25-year sentence, and then worked as librarian at the Bulletin. Older wrote about his relationship with Black in his own memoir, My Own Story.(12)

“The judge sentenced Black to serve one year in San Quentin. After the judge finished, Black arose in the dock with all the ease and grace of an experienced speaker, and talked quietly, most interestingly, for about ten minutes. It was by far the best short speech I had ever heard. It was published in the Bulletin that afternoon.”(13)

Over the Fence in a Baseball

Drug-smuggling was a perennial problem at the jail, long before and long after Jack Black ran his famous operation. The methods of getting the stuff into the jail and distributing it were varied and clever—the best methods, being undiscovered, are of course lost to history.

During prohibition morphine seemed especially in demand. In 1925, Mrs Dong Ho, “aged Chinese of Parajo,” was caught trying to smuggle in large quantities of dope after being sentenced for selling; she thought that as a woman she’d be exempt from search.(14) In 1926 a ring of drug peddlers was busted – they’d been sewing dope into baseballs and tossing them over the 16-foot fence.(15) They also sandwiched it inside postcards sent to friends inside. In 1928 the girlfriend of an inmate was arrested for tucking pinches of dope under the stamps on her love letters to him—using two one-cent stamps instead of one two-cent, so as to maximize the dose.(16)

SF Chronicle, 18 Aug 1928.

Gussie Kennedy, one of the sharper matrons, caught a visitor slipping something to his inmate girlfriend. She sat on him until he handed it over.

Matron Kennedy stops a drug drop in the women's jail. SF Chronicle, 9 Nov 1926.
Matron Kennedy stops a drug drop in the women’s jail. SF Chronicle, 9 Nov 1926.

Park or Penal Colony?

For quite a while, no one did choose to live on the blocks nearest to the Ingleside Jail. Then things began to heat up during the 1910s. More houses were built on that side; nearby neighborhoods were also filling out.

1915 Sanborn map, altered, with additional information through 1920s added. Showing development of blocks nearest the Ingleside Jail.
1915 Sanborn map, altered, with additional information through 1920s, showing development of blocks nearest the Ingleside Jail (marked red-orange, lower left). Click for larger

In 1909 the large 100-acre House of Refuge lot was officially designated a new city park—Balboa Park. There were plans for lovely grounds, a lake, children’s playgrounds, and a deer park—encompassing all of what is today City College and the much smaller current Balboa Park.(17) Almost everything planned was never built.(18)

There came a public outcry to have the jail moved elsewhere. Who would want a massive jail complex smack in the middle of a park? Activists from nearby neighborhoods petitioned repeatedly to have the jail removed.

In 1912 Sunnyside residents accused the jail superintendent of diverting water that should have been supplying Sunnyside homes.

Ingleside Jail is diverting Sunnyside’s water. SF Chronicle, 28 Sep 1912.
SF Chronicle, 1 Oct 1912.

The jail had been cultivating extensive vegetable fields borrowed from the Park Dept to the east of the compound for years. Under Sheriff Tom Finn the gardens expanded to point of such overabundance that the administration sold off most of the produce, largely potatoes and cabbages.

That lobbying, answered by a string of promises from the Board of Supervisors, went on for more than twenty years.

By 1930 a new location was seriously being sought; it took a change in state law to allow SF to build its jail outside the county lines. The new facility in San Bruno was finished in 1934.


SF Chronicle, 26 June 1934.
SF Chronicle, 26 June 1934.
July 1934. Buses transport the prisoners of Ingleside Jail to the newly built replacement in San Bruno, before the jail closes. Judson Hillside visible at rear.
July 1934. A guard oversees buses transporting the prisoners of Ingleside Jail to the newly built replacement in San Bruno, before the jail closes. Judson Hillside visible at rear.

Shortly after the jail buildings were demolished and removed, the site was graded. Perhaps now the long-planned Balboa Park plans could be implemented.

However, two years later the portion of the original jail property, the House of Refuge lot as it was known, on the western side of the railroad tracks (now I-280 freeway) was given to San Francisco Junior College (now City College of San Francisco [history pdf]) for a campus.

What’s in a Jail Name?

There was a change in status from the House of Correction to county jail in 1892, and the institution thereafter was known as branch county jail no. 2. (The jail downtown on Broadway was no. 1.) It wasn’t called Ingleside Jail until about 1906.

In the 1880s, “The Ingleside” was a newspaper and not a neighborhood. By the 1890s there was Ingleside House on the Ocean Road, (at what is now Junipero Serra); the Ingleside Race Track of the late 1890s popularized the name for the area. Soon the branch county jail no.2 was being referred to as “near Ingleside, and then later as “at Ingleside.”

Then, in July 1906, I find the first instance in the newspapers of the use of the name “Ingleside Jail,” in a piece condemning the institution as a deathtrap.(19) All the prisoners from the downtown jail had been relocated there after the Fire in April of that year, and it had perhaps risen in the public consciousness as a result.

And so it was known until its closure in 1934, 58 years after the building’s construction, and 76 years after the property was first used for confining prisoners.



1. “Sheriff’s Ranch a cause for grief,” SF Call, 1 Oct 1912. See also long description in “Town Talk,” SF Daily News, 27 Apr 1918:

2. According to oral histories recorded 2000-2006 by the Sunnyside History Project, available in print at the SF History Center, Main Library.

3. Full breakdown from the 1910 US Census: 310 male inmates; 39 female inmates; The superintendent and his wife and two children; 11 deputy sheriffs; 2 guards; 5 drivers, including one with a wife and five children living there; 1 bookkeeper; 4 jailers; 2 matrons, each having two children; and 1 physician.

4. “Women quit ancient jail,” SF Chronicle, 30 Nov 1930.

5. “Two desperate criminals give Finn the laugh,” SF Call, 5 Jan 1912, p1.

6. Jack Black, You Can’t Win, Edinburgh: AK Press/Nabat, 2000, p246.

7. “Trusties ‘dope’ ring in county jail broken up,” SF Call, 6 Feb 1912, p1.

8. “New clew found to jail delivery,” SF Chronicle, 9 Jan 1912, p9.
9. Ibid., p248.

10. “New Canadian treaty fails to save Black,” SF Call, 1912 Nov 15, p4; “Noted felon arrives; Silent about escape,” SF Call, 25 Nov 1912, p7.

11. “SF jail breaker found in prison,” SF Chronicle, 18 Dec 1918, p15.

12. Available here:;view=1up;seq=7

13. Ibid, p.319.

14. “Prisoner tried to get dope into jail,” SF Chronicle, 31 Jan 1925, p11.

15. “Three in net for smuggling narcotics to jail inmates,” SF Chronicle, 26 May 1926, p3.

16. “Love jails her,” SF Chronicle, 18 Aug 1928, p4.

17. “Perfecting plans for Balboa Park,” SF Call, 12 June 1910, p52; “Balboa Park is to be put in shape,” SF Call, 4 Aug 1910, p5.

18. “More parks are luxuries the City cannot afford,” SF Chronicle, p27.

19. “Ingleside jail is a death trap,” SF Chronicle, 18 July 1906, p3.

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