Legends of Heinold's First and Last Chance Saloon, the Oldest Bar in Oakland

On June 1, 1884, Johnny Heinold handed over $100 and bought himself a salt-encrusted wooden shack at 50 Webster Street, on the Oakland waterfront. When Heinold first came upon the building, it was a lowly bunkhouse for oyster poachers, constructed out of old timbers from a shipwreck. Immediately, though, Heinold saw the building’s greater potential as a saloon. And he was right — Heinold’s First and Last Chance Saloon went on to become a legendary East Bay watering hole and, today, has more than earned its status as a National Historic Landmark.

When Heinold first opened the saloon, it was on the main highway between Oakland and Alameda. It was also located very close to the 1,000-foot-long Webster Street Bridge — then a major thoroughfare. The saloon was on the horse car line that ferried fans to and from baseball games at two different ballparks. Most importantly of all, 50 Webster Street was also surrounded by sea captains, sailors, fishermen and other dock workers who needed a drink or seven at the end of a long day.

It didn’t take long for Heinold’s First and Last Chance Saloon to become beloved by the community around it. The bar was also enormously profitable — Heinold is said to have averaged earnings of $40 a day at a time when $3 was considered a lot. But beyond the money, Heinold loved the saloon dearly for the rest of his life, spending most of his time behind the mahogany bar for close to half a century. In the end, he even died there — friends found him slumped over in a chair there one day in 1933, having suffered a stroke.

But oh, what a storied life Heinold and his saloon had before that. Here are five historical tidbits about both.

Jack London basically lived there

Heinold’s First and Last Chance Saloon’s biggest claim to fame, arguably, is being a major inspiration and favorite hangout of Jack London.

The legendary writer was first given food and shelter at the bar when he was homeless and destitute at the age of just 14, purely because Heinold felt great paternal affection for the boy. Not only did London spend a good deal of time writing in — and about — the saloon, his Oakland High School and University of California education wound up being funded by Heinold himself.

London repaid Heinold over the years, gifting him with autographed first editions, early manuscripts, signed photographs and even his personal dictionary. Heinold put most of these items on display at the bar, making it a hotspot for aspiring writers and creatives for many years. On July 10, 1923, the Oakland Tribune referred to Heinold as the “benefactor of Jack London’s youth, [a] lifelong friend of the famous author and a hero of many a London tale,” before concluding: “A rare friendship existed between the pair.”

Actually observing Prohibition laws

The Bay Area was not good at following Prohibition laws, generally speaking. In San Francisco, North Beach was awash with speakeasies. In the South Bay, Moss Beach Distillery opened up directly next to a cove to make the acquisition of illegal whiskey easier. Marin had its fair share of gin joints too, including the iconic (and still standing) Fireside Inn.

In contrast, the First and Last Chance Saloon spent the 13 long years of prohibition serving only soft drinks and nonalcoholic cider. Heinold complained heartily and frequently about the Volstead Act, once grumbling: “Can you imagine selling soda pop to an old seafaring man? He’d run a harpoon into you.” But he also made sure the law was faithfully observed at his bar, even when it was clear that the end of prohibition was in sight.

On Nov. 22, 1933, eight months after Heinold’s death, the Tribune reported: “Other establishments may jump the gun by selling hard liquors before prohibition legally ends — and there may be places which are selling liquor now — but the First and Last Chance is only serving soft drinks.” The paper also quoted Heinold’s son George, who had taken over the saloon when his father died.

“Old Johnny Heinold never violated the prohibition law,” the Tribune wrote, “and he told his son never to sell it until it is absolutely legal. ‘The First and Last Chance,’ said the younger Heinold, ‘will continue to observe the law, right up to the limit. That was my father’s wish, and the ruling stands.’”

Heinold was old-fashioned (in the bad way)

Let’s not sugarcoat this part: Johnny was not the sort of fellow humans today would probably want to hang out with. For a start, entertainment at the bar frequently involved animal cruelty  — cockfights were common in the 1890s and rats were actively released to test the hunting skills of patrons’ dogs.

Women weren’t particularly welcome in the bar either. For decades, Heinold’s was exclusively visited by men — specifically sailors, fishermen and those that worked at the docks. When women finally started coming to the bar, Johnny was downright repulsed.

On March 30, 1929, The Oakland Tribune reported :

Time was when a woman , no matter what her calling, was always a lady — but Johnny feels the same cannot be said for the modern flapper. Now and then a girl enters his dusty sanctum, buys near-beer and drinks it standing, from the bottle. ‘Gives me the fits and shudders,’ he says. ‘These flappers don’t know what it means to be dignified.’

Oh, boy.

A disastrous fire

In July 1923, a fire broke out at a warehouse occupied by the Hunt-Hatch Commission Company, apparently sparked by a discarded cigarette. Unfortunately, it was directly next to Heinold’s saloon. As firemen struggled to contain the blaze and flames lapped ever closer to the bar, Heinold was told in no uncertain terms to leave the building. He stubbornly refused. When water from the firemen’s hoses started pouring into the building, Heinold nonchalantly put up an umbrella and stayed put.

“It appears to me like there ain’t much chance for a fire here,” he told the exasperated firemen. “More likely to get drowned. No, sir. I’m going to stay right here until there ain’t a stick left. This place has stood right here since Jack London was a boy. He used to stand and gas with me right over this here bar.”

When the fire was finally extinguished, Heinold was ankle-deep in water, but offered the firemen free drinks on the house. A Tribune article published two months later noted that, “the roof and interior of the place were destroyed. Souvenirs of Jack London’s patronage, priceless to Johnny because of their associations, were destroyed … Pictures that date back to pioneer days of Oakland, photographs of long dead civic leaders, were all destroyed.”

Heinold remained undefeated. He pushed on, renovating the bar back to its former glory.

Headline-worthy family reunions

In May 1926, Heinold was reunited with his sister Margaret after not seeing her for an astounding 51 years. Heinold had moved to the Bay from Philadelphia at age 21, when Margaret was only 8, and the two hadn’t seen each other since. The siblings wrote letters to each other over the years, but never actually met up. When they finally did, journalists were on hand to witness the happy occasion. Most of them marveled at Heinold’s greeting: “You’ve grown some, Maggie!”

Following their initial introduction, Heinold took the opportunity to bemoan the lack of alcohol on hand for the occasion. “And to think,” he said. “I didn’t even keep any private stock when I had to turn the bar into a soft drink parlor! All that’s left is orangeade and Coke to drink a toast to our reunion.”

Amazingly, despite Heinold being somewhat of a local celebrity in Oakland, Margaret, it turned out, didn’t even know that her brother owned a bar. “He sent me a picture of it once,” she told reporters, “and I said then I guessed it must be a kind of antique shop…”

Margaret returned to her brother for another visit in 1932 — an occasion that also made the local papers. “This is our second visit,” Maggie told reporters. “The first was about seven years ago — the first time I had seen my brother for 51 years. But to wait another 51 years seemed a bit too long…”

Ninety-one years later, though Margaret and Johnny are long gone, the First and Last Chance Saloon is, miraculously, still standing.