The betting in legal and political circles around town is that Katherine Leonard will be Hawaii’s next supreme court chief justice.

Barring a shocking revelation during her Senate Judiciary Committee hearings, which begin Tuesday, the conventional wisdom is that senators won’t have much reason not to confirm the state’s first female “CJ” and first graduate of the University of Hawaii William S. Richardson School of Law.

But she still could face hurdles, the largest of which would be a negative rating from the Hawaii State Bar Association. The bar is expected to weigh in as soon as today. Leonard, 50, has less than three years experience on the Hawaii Intermediate Court of Appeals and some critics have claimed she lacks substantive administrative experience. Ronald Moon, who will retire Sept. 4 because justices must leave the bench at age 70, is in charge of a state judiciary that employees about 1,800.

Leonard’s nomination was a surprise because it was generally believed that Associate Justice Mark Recktenwald was the best-qualified candidate and a shoo-in for the job, so much so that the commission that puts forward candidates for the nomination had to extend its deadline to find enough candidates willing to be considered for the job.

Finally, politics always plays a factor. This is an election year, and more than half the state Senate is up for re-election or is seeking higher office, including Senate President Colleen Hanabusa.

The Democrat-controlled Legislature will have to decide whether it is more expedient to confirm Leonard quickly, or try to score political points by shooting down a Republican governor’s nominee. If Democrats were able to do that, they could hand the choice over to the next governor, and a Democrat is favored to win.

Civil Beat examines the Leonard pick.

Why Was Leonard Picked?

In Gov. Linda Lingle‘s own words, Leonard is “a person of great character and strong intellect, who possesses effective writing skills and a true commitment to the rule of law.” Her experience includes more than two years on the state’s Intermediate Court of Appeals and serving as a partner with the law office of Carlsmith Ball.

Leonard would be only the third woman to ever serve on the five-member court. She would join 20 women who also serve as chief justice of a state supreme court. A woman was also nominated last month to be chief justice of California’s high court.

In short, a Chief Justice Leonard would be symbolic of women’s progress in the legal profession — and a crowning achievement for a governor bent on taking her political career to the national level.

In picking Leonard, Lingle bypassed Recktenwald, a fellow Republican whom she brought into her cabinet as director of the Department of Commerce and Consumer Affairs and later appointed to the intermediate court and ultimately the high court. Recktenwald has excelled in each position.

But selecting Recktenwald would have meant selecting his replacement as well, and Lingle may not have had time to push another slate of candidates through the Judicial Selection Commission before her term expires in early December. The commission had enough difficulty scraping together the six candidate field that led to Leonard’s nomination.

Better to have three appointments on the five-member bench than leave an appointment to a Democratic governor.

And, despite his Republican stripes, Recktenwald’s record as an associate justice has not always been what Lingle might have expected, most notably on decisions involving the environment versus government and business.

Lastly, Lingle loves surprises — remember her announcement during the 2008 state-of-the-state address about buying Turtle Bay Resort? And, though she would never say it publicly, the Leonard nomination is a nice little payback against the Democrats who tried to extend the retirement age for judges so a Democrat could choose Moon’s replacement.

Who Is Katherine Leonard?

Attorneys who have worked with Leonard agree that she is very smart and highly capable, and that she thoroughly understands the law and how to rule on it.

A “class act,” said attorney Jay Fidell. “Cool, un-ruffable, courageous. I have been through the crucible with Kate, and I have to say she is one of the very few people I hold in high regard.”

Others see her quite differently. They question her administrative experience, her judicial experience and her ability to work with the Legislature as chief justice.

Attorney Eric Seitz — never shy about speaking to the press — told the Honolulu Star-Advertiser that Leonard is “ill equipped and unqualified” for the job, saying that 40 lawyers had serious concerns as well.

Former Hawaii attorney general Michael Lilly disagrees, pointing out in a July 30 letter to the Star-Advertiser that Moon and the late Chief Justice William Richardson did what many CJ’s have done: hire able administrators to run the court system. And the Hawaii Women Lawyers have urged the bar association to give Leonard a qualified rating, saying she possesses both administrative experience and the proper temperament.

Such sharply opposing views are not uncommon in any high-level judicial appointment.

What’s unusual about Leonard — and what may have appealed to Lingle — is that the nominee has not been pinned down in terms of political leanings. While many partners with Carlsmith Ball, whose Hawaii origins date to the middle of the Hawaiian Monarchy, have had conservative legal and political views, those views have not (at least publicly) been associated with Leonard. Nor have her legal opinions revealed clearly which way she leans.

“I was not able to pick up any political or philosophical pattern,” said attorney Robert Thomas, who has posted some of Leonard’s decisions on his blog page. “What I took away from it was I was quite impressed with her writing style and her ablity to communicate well even in arcane issue like tax questions. I thought they were well reasoned, and I was engaged.”

Thomas added, “She’s certainly no Justice Scalia or a Justice Ginsburg, where you can kind of guess what they will write given the case. For the most part they have been pretty consistent in their view of things. I don’t get that sense from Judge Leonard.”

Interestingly, Lingle actually passed over Leonard in an earlier appointment to the Intermediate Court of Appeals, only warming to her later. The governor may well see in the judge a kindred spirit: ostensibly moderate, professionally prim, breaking through glass ceilings that have long seemed unbreakable.

How Will the Senate Vote?

Lingle has been successful with most of her judiciary nominations.

Of her 32 nominations — including some who were nominated and confirmed for one judgeship and then later nominated for a higher seat — only two were rejected: Ted Hong for the 3rd Circuit Court in 2004, and Randal Lee for the Intermediate Court of Appeals in 2007, though Lee had been confirmed in 2005 for the 1st Circuit Court.

The rejection of Hong and Lee both had the taint of politics.

Worried about perceptions of Hong’s lack of judicial temperament as well as a negative recommendation from the Hawaii State Bar Association, the Senate rejected Hong 13-12. In the Lee case, the board was divided on rating him “not qualified” versus “qualified” or “highly qualified.”

Democrat senators said Lee was rejected (by a 16-9 vote) because of reversals of some of his rulings, his prosecutorial background, and lack of civil litigation experience. Lingle then nominated Leonard, who was approved unanimously by the Senate.

The bar’s recommendation is likely to weigh heavily on senators in Leonard’s high-court nomination (the bar ranked her “qualified” for the intermediate court). The bar now only uses “qualified” and “not qualified” ratings, having dropped the “highly qualified.”

Calls by Civil Beat to Lyn Flanigan, executive director of the bar association, were not returned.

What It All Means

The Senate Judiciary and Government Operations Committee is led by Democrat Brian Taniguchi, who was chair when Lee was rejected. There are three other Democrats on the committee (Bobby Bunda resigned late last month to run for lieutenant governor); Sam Slom is the lone Republican.

The Senate, which is not in session, must act within 30 days of Lingle’s nomination, which would be around Aug. 20.

“I think that probably her chances are pretty good — the fact that she is a woman and a Richardson School graduate are two very important political strengths to the appointment,” said Jeff Portnoy, a past bar president. “I don’t necessarily agree either one should be a factor, but I think that’s important as far as the Legislature and the public are concerned.”

Portnoy identified other important factors, many mentioned by both proponents and degractors of Leonard: temperament, intelligence, knowledge of the law, experience, leadership and administrative skills to run the state’s third branch of government.

“I do think she has very strong support among a portion of the bar and, frankly, there is a portion of the bar that do not believe she was the best candidate on the list of six to be chief justice,” said Portnoy. “That’s important.”

If Leonard is confirmed, Lingle’s top legacy as governor may well be on the Hawaii Supreme Court (though James Duffy is hardly considered conservative and sided with the majority on the ruling that Hawaii Superferry required an environmental impact statement before operating). It’s not clear if the governor will testify, but she’s scheduled no public events for Tuesday, perhaps wanting to track the confirmation closely.

For Katherine Leonard, it will be a 10-year appointment to the highest judicial position in Hawaii.

“I am honored and humbled by this appointment and believe I have the capacity, strength and commitment to handle this prestigious position,” Judge Leonard stated when Lingle made her announcement July 22.

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