Fairy tales about princesses and their boundless fortunes typically don’t end like this, with a shock wedding to a decades-younger transexual with a sordid past and questionable intentions, all under a scrim of court-mandated gag orders.

The stupefying denouement of the tale of Abigail Kinoiki Kekaulike Kawananakoa, though, should prompt deeper reflections in this community’s media audiences about what sorts of softly supported storylines they sometimes ingest without protest, especially about their most prominent fellow citizens, such as Kawananakoa.

This polarizing character doesn’t hesitate to boast of being rich, royal and powerful, once even describing herself as the “big cheese” and plopping onto a roped-off throne at Iolani Palace, as a right of her “heritage,” causing a community backlash, leading to the resignation of the palace’s managing director and curator.

Fawning passages of media accounts over the years, including in Civil Beat, have characterized her presence as generating a “sense of awe, respect and deference,” her philanthropic vision bolstering “a wide range of Native Hawaiian issues,” and her athleticism as being so superior she “could have reached Olympic gold in any sport if she had chosen that path.”

Like the tremendous leap in logic that projects a good junior-high-school swimmer into a certain Olympic gold medalist, Kawananakoa’s narrative could be viewed quite differently from alternative perspectives.

Cory Lum/Civil Beat

The Royal History

On a foundational level, the Hawaiian monarchy was overthrown in 1893. Not a single living person remains from that time period, which predates electronic broadcast mass media, such as radio, film and television (let alone personal computers, the internet and smartphones). Historically, monarchies throughout the world faded in relevance during this era, with most of them obsolete and abandoned by World War I.

To imagine a present-day monarchy in Hawaii is an act of speculative fiction, like thought experiments fantasizing about an Axis victory in World War II, a Confederate upset in the U.S. Civil War, or even the British maintaining power in its New World colonies, during their traitorous insurrection.

At the time of the overthrow, the queen of Hawaii, Liliuokalani, already had made her succession plans and bestowed the future throne to Kaiulani. That officially proclaimed princess died just a few years after the monarchy fell, but what would have happened – or could have happened – to the crown from there is all speculation.

Maybe Kaiulani wouldn’t have died, if not under the stress and strain of the situation? Maybe one of the many contenders for the crown would have taken over instead, like what happened in the Royal Election of 1874, when Emma lost the seat to Kalakaua? To automatically assume Kawananakoa would have a title, by fiat, and be the ruler of the kingdom today takes the same kinds of mental gymnastics that also vaults her onto the Olympic podium.

Being a “princess,” by the way, is an adoption of a British title for royalty, not a Hawaiian concept. The ideology of the United States, at its core, rejects such lineage-based credentialing and promotion. Since Hawaii has been affiliated with the United States, not Britain, for more than a century, the House of Windsor-like mentality around Kawanānakoa seems particularly self-serving.

Kawananakoa, in turn, benefits from the best of all worlds. Blonde-haired and blue-eyed, she was born with both white privilege and a claim to Native Hawaiian royalty, supported by an enormous monthly allowance, without ever having to do a day of serious work in her life.

Media reports and public disclosures from her estate estimate her inherited fortune at more than $200 million. Before that big windfall, though, Kawanānakoa struggled to survive on her stipend of about $5 million a year, filing for bankruptcy in the late 1990s. Today, according to various James Campbell Company records, Kawanānakoa (as the largest shareholder) receives a disbursement of about $900,000 a month (or about $30,000 a day). If she runs out, she always can dip into the $200 million, plus, in principal.

Philanthropist Or Just A Big Spender?

With that base level of unearned income and existing reserves, I think a fair question is how “philanthropic” – in relative terms – is Kawananakoa really?

Her donations to various organizations around the community appear large and prevalent from a working-class perspective, and she has promised to give generously to Hawaiian causes at her death.

Kippen de Alba Chu, executive director at Iolani Palace, for example, said Kawananakoa consistently has been the biggest annual donor to his organization, including covering the palace’s annual electrical bills, providing roughly $175,000 a year. Kawananakoa reportedly has given to other local cultural organizations, from time to time over the years, too, such as the Bishop Museum, St. Andrew’s Priory School and the Merrie Monarch Festival.

Yet her largest known gifts to date have been devoted to an out-of-state veterinary-science program at Colorado State University, starting with a $3 million endowed chair position in equine orthopedics, followed by a $20 million “naming gift” announced earlier this year for the CSU research facility.

An examination of the tax forms for her two foundations, Abigail K. Kawananakoa and Ne Lei Alii, show only a few expenses for local projects, such as a combined $100,000 a year to promote scholarships for the study of Hawaiian ancestry. The most is being spent on the curiously listed line item of about $200,000 a year to support a dormant newspaper translation project that still lists its leader as a woman who died in 2014.

The attorney who represents Kawananakoa now, Michael Lilly, and the attorney who served as her longtime advisor but is now estranged from her, James Wright, both declined to publicly comment for this column and about the questions I raise here, including philanthropic issues. So how exactly that money is being spent (and where those translations are) remain a mystery.

Measuring the smattering of donations, in perspective to the size of the fortune, one might ask what has been Kawananakoa’s biggest gift to the community to date? Has she done anything in Hawaii (or for Native Hawaiians) of near significance to the $23 million spent on improving the health of racehorses in Colorado? Anything even in the same ballpark?

Some Native Hawaiians are questioning whether Kawananakoa should still be buried at the Royal Mausoleum at Mauna Ala since her marriage and public fight over the estate.

What will her local legacy of giving be, if we are to furthermore characterize her as a philanthropist? Will the Kawananakoa fortune end up invested in Hawaiian cultural activities and institutions, as promised, or elsewhere, under the direction of a different agenda, set by the new spouse? Even where Kawananakoa’s final resting place will be now appears in limbo.

William “Kai” Bishop Kaiheekai Maioho serves as curator of the Royal Mausoleum at Mauna Ala. He has known Kawananakoa since childhood. She has visited the remains of her relatives at the burial grounds for ruling monarchs of the Kingdom of Hawaii, their families, and close advisors many times. She actively lobbied to be buried there, too, in part as a way to ingrain her legacy among the interred royals and consorts.

Maioho said he gets at least five requests a year for such burials. The original King Kamehameha had more than 20 wives, he noted, and traces of that bloodline (plus other relations to the vast networks of royal families since) creates a diverse cast of characters coveting a spot, jousting over the prominence of their lineage, in fervent pursuit of legitimization. The honor is reserved, though, for only the most well-connected.

Kawananakoa was authorized for burial there in 2013, the first addition to the sacred place since her uncle/adopted brother David Kawananakoa in 1953. Yet Maioho said he has been fielding many calls from Native Hawaiians since Kawananakoa’s marriage, asking about the current status of that authorization.

Those callers often have asked him about assurances that the promised money actually will materialize for Kawananakoa’s opulent crypt construction and the perpetuating costs to maintain it for hundreds of years. Private meetings among stakeholders have been called recently to discuss the matter, including Kawananakoa’s competency to manage her affairs.

At this point, Maioho said, “a lot of things are up in the air.”

Maioho said Kawananakoa has the right to be buried in Mauna Ala, per Hawaiian traditions and the public process undertaken to establish such a right. But her estate will have to pay for the costs. Any status beyond interment at the site is for others to debate.

“I respect her. But I don’t call her ‘princess,’” Maioho acknowledged. “I call her Abigail. Or Ms. Kawananakoa.”