Daniel Jackling made his fortune in copper mining, pioneering open-pit techniques that transformed the industry. The estate he commissioned from Smith -- one of California's most celebrated architects of the Spanish Colonial Revival style -- reflected his wealth and tastes. The mansion featured a built-in pipe organ constructed by the Aeolian Company and later enlarged by George Kilgen and Sons. Smith integrated the residence with landscaped gardens, a traditional courtyard, open-air balconies, and indoor-outdoor sightlines that took advantage of the Woodside setting. After Jackling's wife Virginia died in 1957, the home was sold in 1958, and the surrounding 194 acres were subdivided. The house passed through three owners before landing on the market in the early 1980s with a list price of $3.5 million.

Steve Jobs purchased the Jackling House in 1984 and lived there for about a decade. He later leased it out, then stopped maintaining it entirely around 2000, allowing weather to degrade the structure. In 2004, Jobs received permission from Woodside to demolish the house and build a smaller, contemporary home. The preservation group "Uphold Our Heritage" fought back. In January 2006, a Superior Court judge blocked demolition. Jobs appealed; in January 2007 the appellate court upheld the ruling unanimously. The California Supreme Court refused to hear a further appeal in April 2007. Jobs submitted a renewed permit application in 2008. The town council granted it in May 2009, requiring that the house be offered for relocation first.

In February 2010, a couple named Magalli and Jason Yoho offered to move the mansion to their five-acre Woodside lot. Magalli, who had grown up in a similar Spanish Colonial home in Ica, Peru, said simply, "This house is just a good house for our family." But "Uphold Our Heritage" appealed again in April 2010, triggering an automatic stay on demolition permits. When the legal obstacles finally cleared, the entire residence was demolished. Jobs died of pancreatic cancer on October 5, 2011, before building anything on the site. His widow, Laurene Powell Jobs, proposed a new building for the property in 2016. The Woodside History Museum now houses an exhibit of the mansion's remaining artifacts. The story of the Jackling House is ultimately a parable about Silicon Valley's relationship with its own past -- a tension between preservation and reinvention that the region has never resolved.