Were you unable to attend Transform 2022? Check out all of the summit sessions in our on-demand library now! Watch here.

Steve Jobs hated the historic Jackling House that he bought in 1984 so much that he spent a tremendous amount of time and energy in his final years trying to have the Woodside mansion torn down.

After a decade of controversy and legal fights with local preservation groups, Jobs won, and the 17,250-square-foot building was demolished in February 2011 to make way for a new home.

Jobs’ determination to raze the house was particularly notable because he died from pancreatic cancer just eight months after the demolition. While the extent of his health problems were not well known when the Jackling House was being bulldozed, in retrospect, Jobs must have realized it was unlikely he would live to see anything else built on that land.

So the demolition of the house was one of the last victories of Jobs’ life. In the coming years it will be replaced by a new 15,000 square foot estate proposed by his wife, Laurene Powell Jobs, and moving toward approval by the Town of Woodside.

But it wasn’t quite the end of the story for the Jackling House.

Rather than erasing its existence completely, tearing the house down has scattered many of its remains. While preservationists lost the war to save the house, they continue to fight to maintain the memories and some of physical souvenirs of what they have collectively taken to calling “The House That Steve Jobs Hated.”

The historic Jackling House that Steve jobs spent seven years trying to tear down.

Above: The historic Jackling House that Steve Jobs spent 10 years trying to tear down.

Jobs and Jackling

That certainly wasn’t always the case.

In 1984, with Apple surging and the first Macintosh having just been introduced, a young Jobs purchased the Jackling House and moved in.

Built in 1925, the 14-room mansion was commissioned by a copper mining baron named Daniel Cowan Jackling. He selected one of California’s most notable architects at the time, George Washington Smith, to design it in the Spanish Colonial Revival style.

Aerial photo of the Jackling Estate on display at the Woodside Community Museum.

Above: Aerial photo of the Jackling Estate on display at the Woodside Community Museum.

Image Credit: VentureBeat/Chris O'Brien

Jobs would live there for about a decade. They were years that perhaps witnessed some of his lowest moments, but also eventually the start of his renaissance and a new family.

He quit Apple in 1985, about a year after buying the house, amid a power struggle caused by the failure of the Mac. He then started NeXT, another computer company that largely failed — although it was eventually bought by Apple, bringing its operating system and Jobs into the company.

Above: A photo from Friends of Jackling House.

Image Credit: Town of Woodside

He was still living in the house when he met Laurene Powell, then an MBA student at the Stanford Business School. They married in 1991, and Jobs’s first son, Reed, was born while they still lived in the house. Eventually, the couple relocated south to a home in Palo Alto.

By the end of the 1990s, the Jackling House sat largely empty, and Jobs allowed it to fall into decay (see a photo gallery here), with windows and doors left open, allowing moisture and vandals to take their toll.

Above: The Jackling House in Woodside, before it was demolished.

Image Credit: Google Maps

In 2001, insisting the house was unsalvageable, Jobs asked the town of Woodside to let him tear it down. The town eventually approved the request, but local preservationists banded together to appeal. The legal fight lasted nearly a decade — until 2011, when an appeals court finally gave Jobs permission to raze the structure.

In February 2011, the bulldozers moved in.

The lot after the Jackling House was demolished and all the construction debris removed.

Above: The lot after the Jackling House was demolished and all the construction debris was removed.

Image Credit: Google Maps


Apple logo wall hanging spotted inside the Jackling House.

Above: Apple logo wall hanging spotted inside the Jackling House.

Image Credit: Courtesy of John Haskey

The sound of music

A few weeks before the demolition began, with the clock ticking, Dick Tagg, a Woodside community activist and volunteer, was talking with a friend on the phone about the pending demise of the Jackling House.

The friend (who requested anonymity to protect his privacy) was a pipe organ enthusiast. The two were were exchanging memories of the pipe organ that had been placed inside the Jackling House back in 1931 and wondering what would become of it.

A couple days later, they were on the phone again, when the friend said something that almost knocked Tagg over.

“‘You know, I think I own that organ,'” Tagg recalls him saying. “I thought he was joking.”

Nope. Years earlier, Jobs had offered this person the organ, and legal documents were signed and then forgotten. Until now.

With only a short window, the friend called on a group of pipe organ enthusiasts to help him salvage the instrument. It was a massive job.

The organ had an elaborate infrastructure of 3,300 pipes knitted into the house’s infrastructure, plus the massive keyboard console. It was designed to be played by an individual or automatically.

“Long ago, in the days when radio was a toy for amateurs and phonographs were still acoustic, if you wanted music in your house and were ‘of means,’ you bought a pipe organ,” says the website for the group, which called itself the Friends of the Jackling Organ. “Since you didn’t actually play, you made sure it came with an automatic player. You could then relax in the evening while the butler put on rolls of whatever kind of music you fancied.”

What the group found when they arrived at the Jackling House to begin disassembling the organ was depressing, to say the least.

“The console had been badly damaged,” Tagg said. “Someone had built a fire on it, if you can imagine.”

Above: The organ that was salvaged from the Jackling House.

Image Credit: Friends of Jackling Organ

The work took weeks. John Haskey, a Silicon Valley engineer, was one of the folks recruited to help. He grew up listening to his mother play organ in church and remained passionate about the instrument.

“After you’re writing software all day, sometimes it’s nice to get back to the old technology where you can put your hands on it,” he said.

The group chronicled their work in a gallery here. Eventually, thousands of pieces were removed and placed in a rented storage shed somewhere in the hills, Haskey said.

“‘Salvage’ is the right word,” Haskey said. “A lot of it was in really bad shape. And that was really a shame.”

After several years of trying, the group never did find someone willing to take on the work to rebuild the organ.

“It is now owned by an organ builder in the San Francisco Bay area and will likely be parted out, i.e. sections of it used in various other organ projects,” Haskey wrote in an email this week. “It’s sad that we were unable to find a patron who could support the restoration but with storage costs, etc. we ran out of time and resources.”

The leftovers

For some period of time, Jobs did try to find someone who would be willing to take the whole Jackling Estate and relocate it. But when that effort failed, he agreed to let the town of Woodside salvage whatever it wanted from the house in terms of ornamentations and fixtures.

And so, in the weeks before demolition, a group of volunteers scoured the house looking for anything that could be easily removed and preserved.

Thus began a frenzy that resulted in the removal of several trucks full of items, including the house’s copper mailbox, intricate roof tiles, woodwork, fireplaces, light fixtures, and moldings that were all very period-specific and once-fine examples of the Spanish Colonial Revival style.

Artifacts salvaged from the Jackling Home, on display at the Woodside Community Musuem.

Above: Artifacts salvaged from the Jackling Home, on display at the Woodside Community Museum.

Image Credit: VentureBeat/Chris O'Brien

Having salvaged all this stuff, the town faced another dilemma: What now?

The first thing the council decided was to create an exhibition in its community museum called “Days of Grandeur.” The exhibition includes some of the more notable items from the house, as well as recounting the history of its first owner:

“The exhibit tells the story of Daniel Jackling, who was orphaned at the age of two and rose to become one of the most important and influential figures in early 20th century America,” reads the description. “Daniel Jackling’s successes in the field of copper and mining allowed him a grand lifestyle of private rail cars, yachts and world travel.”

The salvaged material also included a 50-foot flagpole the town plans to install permanently in front of the community museum.

Beyond that, the town still has a storage unit full of some of the remaining artifacts removed from the house, most of them in disrepair.

Town officials have contacted various museums and historical associations, with no luck so far. They’re still hopeful a solution can be found. But with talk of closing the exhibit after four years, the storage problem may be about to get worse.

“The artifacts are still a very valuable resource,” said Thalia Lubin, a Woodside architect and a member of the Woodside History Committee. “But I don’t know what we’re going to do with them.”

Jackling House exhibit at the Woodside Community Museum. Photo by Chris O'Brien

Above: Jackling House exhibit at the Woodside Community Museum.

Image Credit: VentureBeat/Chris O'Brien

New life

Benjamin Gilad and Qian Su, both Silicon Valley software engineers, had a suggestion.

In 2012, the couple bought land at 205 Whiskey Hill Road, a heavily wooded property just across the street from the Woodside Town Hall. They wanted to move a small, historic blacksmith house to a different location on their property and build a new, elegant residence in its place.

In thinking about the style they wanted, the couple sent their architect to study the Jackling exhibit at the community museum. While drawing up the plans, the architect found “inspiration from many of this past home’s details,” according to town planning documents.

So the couple asked: Could we buy some of the salvaged pieces to use in the construction of the new home?

“The owners of 205 Whiskey Hill wish to acquire and incorporate certain of these salvaged items into the construction of their George Washington Smith inspired home,” reads a report from the town planning staff. “The History Committee expressed their support for this disposition given that the items could then remain in Woodside and be incorporated into a Spanish Colonial Revival home fashioned after the architecture of George Washington Smith. The items requested include architectural details such as decorative wood corbels, and wrought iron details and fixtures. These items are not in pristine condition, many would require significant effort to be fully restored or incorporated into a home as originally used.”

And that was just fine with the owners, Gilad and Su.

“They are in great need of care and love,” Su said in an interview. “We both like to work with our hands. So we thought this was a good opportunity to give these items a second life. And keep them in a town that has shown that they are important.”

Alas, easier said than done.

Figuring out a system for determining the value of the items and a system for selling them, including identifying possible buyers, became too complex for the town officials.

Eventually, the request was dropped, and the couple moved on with their construction plans without any Jackling artifacts.

Above: Construction underway at 205 Whiskey Hill Road for a house inspired by the Jackling Home.

Image Credit: Google Maps

One more thing

The last part of the Jackling Estate saga is only somewhat related to Jobs. It turns out that when Jobs bought the Jackling House in 1984, the original Jackling Estate had been subdivided.

An adjacent lot to the north contains the Jackling stables, a massive structure known as the Champagne Paddocks. It was built in a similar architectural style to the main Jackling House, though designed by a different architect. Most of the lot is rolling fields.

The Champagne Paddocks were bought in 2000 by another notable name in the world of technology: Netscape cofounder Jim Clark. He purchased the property for a reported $50 million at the tail end of the dot-com bubble.

Unlike Jobs, Clark had no desire to tear down the Champagne Paddocks. Rather, he wanted to move the stables somewhere else on his property and preserve the central tower as part of a larger complex of buildings.

That cheered town preservationists, who were already distressed about Jobs’ request to tear down the Jackling House and were eager to see what Clark had in mind.

“The owner is interested in creating a rural residential retreat,” project architect Charles T. Young told Woodside’s Almanac News in 2002.

But then, nothing happened for almost a decade. Clark finally re-emerged a couple of years ago with ambitious plans that were submitted, debated, vetted, and finally approved by the town. The proposal included a main residence of 7,960 square feet, with 4 bedrooms, 5 baths, and 4 half baths, a subterranean garage of 3,861 square feet, a pool house of 1,304 square feet, a 46-foot swimming pool, and an equestrian riding arena.

After all that effort, however, Clark threw the town another curveball: He decided to sell the whole thing.

“Jim Clark bought the property with the intention of building one of Silicon Valley’s grandest estates,” Michael Repka, the agent who is handling the sale of the property for real estate firm Deleon, wrote in an email. “However, as time went on he found that he was spending most of his time with his family in Florida and NY. Given his decision to live in Florida rather than California, it made sense for him to sell the property.”

The Clark property at 201 Mountain Wood Lane is now for sale for $15 million. The price includes the 8 acres of land, the Paddocks, and architectural plans that have already been approved by the town of Woodside. Of course, after buying the lot, one would then also have to cough up the money for the construction.

In the quest to find a buyer, the real estate firm has created a promotional video that not only shows the plans and land, it also name-drops several of the neighbors, including Oracle’s Larry Ellison, and mentions the land owned by Jobs.

Behold, the land and the details of the proposed construction, in all their splendor:

And in the end…

While Clark is leaving behind his real estate dream, just down the street, Jobs’ widow, Laurene Powell Jobs, is on the cusp of realizing her family’s vision of Silicon Valley splendor.

Her proposal, which places a thoroughly modern residential complex amid an agricultural paradise, is moving toward approval by the town council sometime this year. If approved, her project will at long last replace the structure built by a giant of commerce from another era, which was bought and then demolished by one of the greatest titans of the technology age.

It will bring her back to the place where she and Steve Jobs first started their life together. And it will create a distinctive residence that, like all grand estates of a gilded age, aspires to endure as a monument to its creators and their tastes.

But even before a single shovel hits the ground, it’s hard not to imagine that whatever Powell Jobs builds is inevitably a temporary marker. Whatever hopes of permanence she may have for the new estate, it may simply be the next placeholder until some future landowner comes along in a few decades and decides they would rather just start from scratch.

VentureBeat's mission is to be a digital town square for technical decision-makers to gain knowledge about transformative enterprise technology and transact. Learn more about membership.