Evil spirits were thought to be the only inhabitants of Lanaʻi prior to about 1400, when settlers arrived from Maui. Little recorded history exists but there are traces of a thriving fishing culture along the coasts, especially to the north and east. Raiding parties from other islands were a frequent terror.

Colonialism largely bypassed Lanaʻi, although diseases brought by the odd missionary decimated the population from several thousand to 200 by the 1850s. Everything changed when Charles 'George' Gay began buying up the place in 1902. Within a few years he owned 98% of the island (a holding that has remained almost unbroken through various owners to this day). In 1922 Lanaʻi passed into the hands of Jim Dole, who started a pineapple plantation that was soon the world's largest.

Under Dole (and later its corporate successor, Castle & Cooke), Lanaʻi was not just a company town but a company island. Early managers were de facto dictators, who were known for spying on residents from their hillside mansion and ordering guards to discipline any deemed to be slackers.

In the 1980s Castle & Cooke and its hard-driving main shareholder, David Murdock, made plans to shift Lanaʻi's focus from pineapples to tourists. The final harvest of the former occurred in 1992, the first resorts for the latter opened in 1990.

Over two decades the company struggled to find a profitable future for the island. In 2012 Larry Ellison, the billionaire CEO of software giant Oracle, bought the island. Since then many grand visions for Lana‘i have been floated, although realizing them has been problematic.

Life With Larry

Decades of sleepy seclusion for Lanaʻi were interrupted in 2012 when the fabulously wealthy cofounder of huge software developer Oracle, Larry Ellison, bought out the island's long-time owner Castle & Cooke (which once ran the ubiquitous pineapple plantations under the Dole name).

It's the biggest change to the island since Castle & Cooke stopped farming and built the Four Seasons resorts in the early 1990s. That the owner is a legendary hard-driving Silicon Valley entrepreneur known for, among other dramatics, winning the America's Cup twice (most recently in 2013), only adds to the interest.

For his estimated $600 million purchase price, Ellison got 98% of Lanaʻi (the rest is private homes or government land) and a bevy of businesses, such as the resorts. Given that the island has struggled economically since the glory days of pineapples, Ellison's wide-ranging plans for his trophy generated intense interest.

Under the guise of Pulama Lana‘i, the Ellison-owned company that manages the island, the changes have been many. Among the notable events are the following:

  • Construction projects to rebuild parts of the island infrastructure, enact beautification schemes and revitalize core businesses such as the Four Seasons Resort Lanaʻi put a major strain on the island. During 2016, both of the resorts were closed; the resulting dramatic downturn in visitors caused several long-running businesses to close.
  • Ellison has discovered that just because you own an island doesn't mean that you’re exempt from government regulations. Regulatory hurdles and local political opposition have delayed projects including a new beach resort at Halepalaoa. Issues surrounding approval for a desalination plant caused initiatives like a vast conference center to be put on hold.
  • During 2016 and into 2017, there was a noticeable slowing in new proposals, leading many locals to fear that the political difficulties had caused Ellison to lose interest in the island and turn his famously high-intensity attentions elsewhere.

For residents, life on Lana‘i feels a bit like a soap opera as plans and schemes are floated and then forgotten. Ellison has said he wants the island to be economically self-sufficient, yet achieving this may be the biggest challenge of his life.