In December 2019, during Apple’s only open day for the public at their headquarters, former Cupertino Mayor Gilbert Wong took a rare tour of the facility. In an exclusive interview, he shared insights from his experience negotiating contracts with Apple while he served as mayor. Wong recalled a clandestine meeting where he was shown the highly confidential blueprint of Apple’s headquarters, led by none other than Steve Jobs himself, as they engaged in intense discussions with Apple’s celebrated CFO, Luca Maestri.
Wong’s journey with Cupertino began in 2002 when he joined the city planning commission. He later transitioned to the city council, serving from 2007 to 2016, and held the mayoral position in 2011 and 2013. Notably, during his tenure as mayor, he played a crucial role in approving Apple’s decision to establish its headquarters in Cupertino, which required negotiating successfully between the city staff and Apple.
In 2010, while serving as Cupertino’s vice mayor, Wong received an unexpected phone call from Apple inviting him to a meeting. He anticipated a casual visit, but it turned into a significant encounter with Steve Jobs. Despite his battle with pancreatic cancer at the time, Jobs engaged Wong in a discussion about acupuncture and its health benefits.
As the conversation shifted to Apple’s plans for its new headquarters, Wong vividly remembers Jobs saying, “Gilbert, I want to invite you into this room to see our next project. Can we step into this dark room?” Jobs then retrieved a key and opened an inconspicuous door, which revealed a breathtaking sight: a large model of what would become the future Apple campus.
Wong described the model as “a complete representation of the Apple headquarters, featuring tables, people, trees, cars, and even a four-story cafeteria.” Witnessing this model of an architectural marvel left Wong deeply moved, as he and Jobs discussed various technical aspects, including the building’s height and design setbacks.
Negotiating with Apple wasn’t without challenges, as Wong candidly admitted. In 2013, Maestri reached out directly, stating, “I need to talk to you; the city council needs to approve the Apple headquarters plan.” At the time, Wong was preparing to take his family on a hike and prioritized family time over business. “Can you call me back later?” he asked.
Later that afternoon, they spoke again, and Maestri highlighted the urgency of moving forward with Apple’s project. Wong insisted that the residents of Cupertino required the expansion of the nearby Wolf Road overpass from four lanes to six, with Apple bearing part of the costs. “If you can let Tim Cook know, I’d like to see a six-lane interchange; residents need more lanes to cross I-280 and access Wolf Road,” he explained.
The negotiation process required some back and forth because Apple was initially hesitant about the extra expenditures. However, by October 2013, an agreement was reached on the Wolf Road expansion project, with Apple agreeing to fund the initiative. Construction is expected to commence between 2024 and 2025, once sufficient funds have been secured.
Wong also pointed out that recent audits from the California Tax Board regarding Apple’s online sales tax would not impact this project, as those tax issues were unrelated.
Reflecting on his negotiation experiences with Apple, Wong emphasized the importance of his role as a council member and mayor in facilitating development in Cupertino. He revealed that during the negotiations, he faced threats from others, especially during his second term as mayor. “It was a challenging moment, but I wasn’t afraid,” he said with confidence.
Wong still treasures the visitor badge from Apple’s open day in 2019, which serves as a reminder of a pivotal moment in Cupertino’s history.
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