Say’s critics see him as emblematic of Ჹɲʻ’s “old boys’” style of politics. He defends his cautious style as necessary to keep the state running smoothly.

Looking back, it can be easy to forget that gay marriage was one of the most controversial issues of the 2000s.

Ჹɲʻ voters removed an amendment from the state constitution this past November that gave lawmakers the explicit power to outlaw gay marriage, a pleasant surprise to some who worried the question’s wording veered too technical. 

But public sentiment was far different almost 20 years ago. Opposition was much stronger, and many lawmakers worried that taking a position on such a polarizing issue could cost them politically. 

So when a bill to allow civil unions for same-sex couples reached House Judiciary Chair Tommy Waters in 2007, Speaker Calvin Say gave him advice: Don’t schedule a hearing. 

“Are you looking for higher office?” Say remembers asking Waters and other committee chairs who decided whether to hear controversial bills. “Are you looking to continue in public service?” 

Waters killed the bill. 

Honolulu City Council member Calvin Say.
On the City Council, Calvin Say took on an elder statesman role, frequently raising concerns about financial and enforcement practicalities when other members introduced bills. (Cory Lum/Civil Beat/2022)

It saved House members from having to take a stand on a politically toxic issue, at least for the time being. But in the aftermath, Waters faced heavy criticism for not holding a vote. He left public office the next term, returning six years later for an unsuccessful Honolulu City Council campaign before winning the next election in a close rematch.

Say said his questions towards Waters were meant as wisdom.

“It’s not a threat,” he said. “It’s the truth.”

He often shares politically cautious advice like this with younger colleagues, leaning on his decades of patient learning. 

Say was already the House’s senior member by the time he became speaker in 1999, and he remained in the House for another 21 years. When his council term ends Thursday, he will have been in elected office for almost three-quarters of Ჹɲʻ’s entire history as a state. Pivotal events both affected his career and were products of his own choices.

Say’s critics see him as emblematic of Ჹɲʻ’s “old boy” style of politics, where progress is slow and behind-the-scenes favors decide which bills live and die. 

His supporters don’t argue the facts. But they frame them differently, arguing that Say recognizes all politics is personal, and that he knew how to keep his fellow legislators happy.

“He was born and raised politically in a time when that old boys’ network was the strongest it’s been,” U.S. Rep. Ed Case said. “I think he worked with it. I think he understood it. But I don’t believe it’s correct to characterize him as part of the old boys’ network.”

Path To Power

Say first won elected office when he was 24 years old in 1976, his second attempt. 

A part-time busboy at the Old West-themed restaurant Flamingo Chuckwagon on Kapiʻolani Boulevard, he and a few coworkers had gone out for drinks one night and egged each other on to run for office. 

“They were upset that the incumbents did not campaign,” he said. 

Those incumbents — part of the generation of Japanese-American World War II veterans who served on the 442nd Regimental Combat Team — were known to the parents of Say’s generation, but not as much to his peers.

In 1976, freshman Rep. Calvin Say thought state legislators should be limited to three or four terms. He ended up serving 22. (Screenshot/Newspapers.com)

His initial years were quiet. 

“I just wanted to learn,” he said.

He worked his way up, chairing increasingly powerful committees: first the Culture and the Arts Committee, next the Tourism Committee and finally the Finance Committee in 1993.

It was a difficult time to be Finance chair. The country had just had a recession, and regrowth was slow because of fewer tourists, less foreign investment — especially from Japan — and a declining sugar industry. 

Finding money to balance the budget meant making tough decisions. One big pot of money Say came after was government pensions, earning the ire of public unions.

He also played tricks. 

Beyond writing laws — which can be too abstract for the average constituent to appreciate — legislators care deeply about getting money for visible infrastructure projects in their districts. 

During budget negotiations with the Senate, Say would make up projects in his own district of Palolo, St. Louis Heights and Kaimukī. Then — as a bargaining chip — he would offer to slash them from the budget.

Still, Say’s antics at the time were pedestrian compared to his mentor’s, Speaker Joe Souki.

Souki twisted arms, holding bills in committee as bargaining chips for lawmakers’ votes. By the end of the 1990s, many House members were dissatisfied with his leadership, especially after a controversial episode featuring the wealthy Bishop Estate.

The Kamehameha Schools located on the slopes of Kapalama.
The main campus of Kamehameha Schools overlooks Kapālama and Kalihi. In the late 1990s, its trustees came under fire in a high-profile investigation into mismanagement of the trust. The fallout helped lead to Calvin Say taking over as House speaker. (Cory Lum/Civil Beat/2021)

As detailed by and later the book “Broken Trust,” financial mismanagement by trustees of the Bishop Estate — now known as Kamehameha Schools — led to outcry over how trustees were selected and their high compensation of almost $1 million per year.

Souki had defended the politically connected estate, leading to backlash from House members like then-state Rep. Ed Case who wanted to cap trustees’ compensations. 

A bill to do so failed by one vote at the end of the 1998 legislative session. But outcry continued, and two days later, the bill was revived and passed almost unanimously. (The single dissenting vote . Years later, he said in an interview that he believes the trustees’ investment performances justified their compensations.)

“By the end of that process,” Case said, “most of the members of the House were ready to move on in leadership.”

Constituents were also dissatisfied. 

Democrats had dominated the Legislature since statehood, occupying 45 out of 51 House seats following the 1990 elections. But as the decade wore on, frustrated voters chipped away at the Democrats’ supermajority, electing 19 Republicans to the House in the year 2000. Linda Lingle, a Republican, lost the gubernatorial election by less than 2 percentage points the election before.

This confluence of pressures — from members and from voters — gave Souki dissidents enough leverage to vote him out. But it begged a question: Who in the House had enough appeal from both dissidents and the Old Guard to replace Souki as speaker?

Speaker Say

“Calvin was the natural choice,” Case said.

As Finance chair, Say avoided feuds and ideological struggles. He was close enough to leadership that he knew how to run the House, but was generally well-liked and seen as a consensus candidate for speaker. 

Case was one of the first to pitch him for the position. Saiki, who later led a yearslong effort with now-Lt. Gov. Sylvia Luke to overthrow Say, also lent his support. 

Rep Marcus Oshiro on abortion bill. Can't remember if he was opposed or supported. 11 april 2017
As Finance chair, former Rep. Marcus Oshiro worked closely with Speaker Say. If he was at all hesitant over how to vote on a proposed bill, Oshiro said, Say’s advice was to just vote against it. (Cory Lum/Civil Beat/2017)

But their support was short-lived. Say is an incrementalist, and that frustrated lawmakers who wanted big reforms done quickly.

Civil service reform was a top issue at the time. Overtime was inflating pension calculations, merit-based advancement was weak, and recruitment and retention were poor.

“We were asking it to be responsible for advancing a state with a lot of problems,” Case said.

A civil service reform bill had passed the House, the Senate and was in the gauntlet of conference committee. Case, who by then was majority leader, thought it was going to be approved. But he said the House Finance chair at the time sabotaged the bill, and that Say as speaker allowed that to happen.

“People wanted change. And I thought that the pace of change was too slow,” Case said. “And I was disappointed that a lot of very, very good work to solve literally one of the top three challenges facing Ჹɲʻ had been taken out.”

While it wasn’t the only reason, Case and the leadership team parted ways soon after. 

Say appreciated Case’s perspective, and said he was correct on the merits. But he disagreed with Case’s pace.

“You got to be consistent every year trying to chip at it chip at it chip at it. Because they had members who are so afraid of the public employee unions,” Say said. “So that’s where I think Ed missed out. He wanted to do it now. Very impatient.”

Case wasn’t the only one who felt this way. 

Saiki became majority leader shortly after Case but soon enough also parted ways with House leadership.

He, first-term Rep. Della Au Belatti, and then-Rep. Sylvia Luke implored their colleagues to vote against Say’s leadership , citing what they saw as self-dealing and a lack of progress on issues like renewable energy and a tax credit for working families. 

They were the three lone votes against Say that day, not to be joined by a majority of their colleagues for six more years.

Speaker Emeritus Calvin Say's Palolo house showing Kaimuki in background10th Ave. on September 17, 2014
While he served in the House, some of Say’s constituents claimed that he did not actually reside in the district. They argued that he instead lived outside the district at his wife’s place in Pauoa. A House investigation concluded that he could maintain his seat because he technically intended to return to his Palolo house, fulfilling the definition of residency. (PF Bentley/Civil Beat/2014)

In the meantime, Say continued dominating the role and forcing incrementalism. He let meetings run late into the night, exhausting committee members so he could swoop in and negotiate a deal. 

He built personal relationships through hosting dinners at then-Rep. Kirk Caldwell’s house in Mānoa, inviting his supporters as well as fringe House members to ensure he had their votes.  

“There are people who are really good at vote counting,” Caldwell said. “And Calvin Say is really good at vote counting.”

Say had a talent for keeping his members happy. A decade before serving as Honolulu mayor, Caldwell entered the state House and hitched himself to Say’s leadership team despite feeling they were more conservative than he was.

“I felt there was greater trust with Calvin,” Caldwell said. “If he gives you his word, his word is good.”

Caldwell was motivated by his time in Boston. In college and after graduation, he commuted via the Massachusetts Bay Transportation Authority’s rail line, better known as the “T.” 

He wanted to bring a rail line to Honolulu. And as vice chair of the House Transportation Committee under Say’s leadership, he got to work on how to fund it. 

“I benefitted from something that the people of Boston sacrificed to build a hundred years before I got there,” Caldwell said. “He put me on that committee because I wanted to work on rail.”

Mayor Kirk Caldwell Rail speaks about his Conceptual Plan during press conference held at the Airport.
Former Rep. Kirk Caldwell ended up becoming Honolulu’s mayor, a position he used to help continue his push for rail. His departure from the Legislature left Say with one fewer ally. (Cory Lum/Civil Beat/2020)

Say credits his longevity in part to Lingle, the Republican, becoming governor. That fueled demand among his members for a strong, proven Democratic House speaker. But no speaker lasts forever.

Dissatisfaction against Say grew over the years. His loyalists — like Caldwell — were leaving the House for other ventures, replaced by newer members who saw Say as somebody who had overstayed his welcome. 

“There was generational change,” Saiki said. He and Luke joined forces with House Republicans in 2013 to overthrow Say and reinstall Souki. 

For Say’s remaining seven years in the House, he chaired no committees, leaving for the City Council in 2020 when a seat opened up.

Uncle Cal

As a City Council member, Say remained fiscally cautious. He asked testifiers questions in order to educate other council members. He showed up personally to neighborhood board meetings rather than sending a staffer. He focused on practicalities, killing bills that he thought weren’t sound financial decisions and speaking out when he worried about implementation.

When lifeguards wanted their own city department, Say refused to hold a hearing as chair of the Budget Committee.

When larger setbacks were approved for wind turbines, he lamented that the housing units his district hosts would need to find its energy elsewhere. 

And when the recent empty homes tax bill came up for a final vote, it was deferred after it became clear that Say, who would have been the tiebreaker, was poised to vote against the bill. That bill will likely come up again next year once a city-commissioned study is complete.

Honolulu City Council member Calvin Say listens to public testimony during floor session.
Like his former counterpart Carol Fukunaga — who co-chaired the Senate Ways and Means Committee at the same time Say chaired the House Finance Committee — Say started appreciating the role of county government more after he became a council member. (Cory Lum/Civil Beat/2022)

Sometimes, he complained that the state’s actions make the counties’ jobs more difficult. When pressed, he acknowledged that some of these grievances might come from his own past actions as a state representative.

One example: The City and County of Honolulu has struggled for years to find a spot for its new landfill, settling recently on a spot . A big reason is that state restrictions passed in 2020 prohibit placing a landfill within half a mile of schools, hospitals or residences. Say griped against the state’s restrictions, arguing they tie the city’s hands.

“I didn’t create those conditions,” he said. “It’s the Lege that did that Act 73, and the city has to abide by it.”

But Say was in the House when the restrictions passed. His vote helped approve the bill. 

Now, Say thinks state law should be amended. Oʻahu legislators should agree because everybody on Oʻahu is affected by the landfill issue, he said at an October council meeting, citing societal practicalities and a strong potential voting bloc. 

“We just go and see our colleagues who are state legislators from Oʻahu,” he said. “They have the majority. And this is affecting Oʻahu as a county. They’re all going to face the music, one way or another. Not just Calvin Say.”

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