One of Auckland’s best-known judges and lawyers has officially retired, but it’s hard to tell. In an exclusive interview, Simon Moore tells Carolyne Meng-Yee about swapping counsel’s robes for the bench, the importance of empathy, cases that unsettle him, being likened to a mix of Donald Trump and Denny Crane
Simon Moore KC: On famous cases from Pitcairn Island to Grace Millane and life after law
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Former Crown solicitor and High Court Judge Simon Moore is now chair of the Electoral Commission and the sole member of the public inquiry into the Tom Phillips case. Photo/ Dean Purcell
On a stand nearby is a horsehair wig, a gift from his parents, Sir Patrick and Lady Elizabeth Moore, when he was admitted to the bar in 1982. Not that Moore, 72, will ever need to wear a wig or a toupee. His magnificent head of hair has caused some controversy. Today’s pressing business is not crime but confirmation of his six-weekly appointment with Phil the hairdresser.
These days, Moore is a director and consultant at law firm Tavendale and Partners, after retiring from the High Court two years ago. He is also the chair of the Electoral Commission and the sole member reviewing the Tom Phillips case.

His eldest son, Henry, also a partner at Tavendale, is now his boss. (Edward is also a lawyer and Matthew is a banker.)
Moore jnr says his father is the real boss, who brings energy and fun to the firm.
“Dad is Dad — he typically turns things around before a deadline. He’s willing to help, and nothing is ever a problem."
We asked “Dad” for his views.
What’s Henry like as a boss?
Joining this firm is like going back to the future for me. It’s lovely being in an intimate practice which has very traditional high standards and values. I wouldn’t have joined if it didn’t have them. Henry won’t do litigation law in the way I’ve done it, so it’s great. To sit alongside Henry and help with some of the tactical things is fun. I also provide advice on litigation risk.

Describe your childhood
I had a blissfully happy childhood with wonderful parents. My father was a pioneering ear, nose and throat surgeon. He was fluent in te reo and a doctor to the 28th Māori Battalion. A kaumatua said to me, “Do you realise that your father held the hands of more dying Māori than probably anyone?” That was significant.
Two siblings followed Dad in medicine, and my younger brother also did law. I initially trained as an archaeologist, but my wife didn’t think there was a huge future in that.
You’ve been married to Jane since 1982; how did you meet?
In Dunedin, Jane studied food science and was very talented. When she first started working, she earned much more money than I did as a young lawyer. She gave that up when we started having children and allowed me to develop my career.

What are some of the highlights from your legal career?
I loved being a law clerk at Meredith Connell. To serve as a Crown solicitor for 20 years was a privilege, something I never dreamed of. Being a judge was an absolute highlight; part of that was the people, we were all doing this job together. It wasn’t like a partnership where you talk about, you know, fees and remuneration, money never came into it. We were all doing this job because we wanted to serve.
Do you miss it?
Yes, I do. I miss it a lot.
Why didn’t you become a defence lawyer?
It was my liberal upbringing that I had from my parents, a sense of helping the underdog. It was imbued in us as children to be generous, and I didn’t like the idea of clubbing people. With prosecuting, you can do so much good; you can help victims of crime and defendants too.

Do you think that getting justice these days depends on the size of your wallet?
There’s no doubt at all that litigation is incredibly expensive. It is something I know our Chief Justice is very conscious of: the accessibility of justice and how we make justice more accessible to those who need it. There are various reforms taking place, with much more emphasis on pro bono [free legal representation] now - certainly all of the larger firms have pro bono programmes.
What is it like being the chair of the Electoral Commission - is it boring?
It’s not boring, it’s a complex beast. There are 2500 voting places that need to be vetted, and significant changes. People will have to enrol early, and 5% of North Island voters will be voting in a new electorate because of boundary changes. Some 28,000 staff need to be trained; there’s no room for mistakes.
If there’s one message I want to get out, it’s the need to reduce the number of special votes. They take 10 times longer to process for the official count, and governments can’t be formed until that’s completed. The price of failure is very public, and I’m not prepared to go there.

It’s been reported that your daily fee for the inquiry into Tom Phillips is costing $1680 a day, up to four days a week. The report’s due in July, how are you tracking?
Counsel assisting me are on $300 per hour, compared with the pro-rated $210 I am on. My private rate is up to $700 an hour. I can’t say too much about the inquiry other than the core agencies that are identified in the terms of reference have been very cooperative and helpful, and I’m working very closely with them.
How could things have been done differently?
That’s one of the things we have been asked to look at that may form part of my recommendations. There are extensive suppression orders in the High Court and Family Court, and I’m not going to breach them.

How difficult is it to transition from being a lawyer to a judge at the High Court?
In a criminal trial, you’ve got your opening to the jury, you’re leading your witnesses, you’ve got the cross-examination, you’ve got your closing addresses - all adrenaline-driving experiences.
You live that trial for the duration of the trial, then have a drink afterwards. I loved being the Crown solicitor, so it was difficult to make that move to the bench because I knew that my ability to self-determine was going to be compromised.
As a judge, it was hard to adjust to cases arriving on my desk with little or no control. It’s a conveyor belt where the work just comes through. Also, the discipline of having to write judgments, straight away; if you’re not efficient, you will drown.

And you must get it right. The worst thing that could happen is for the judge to screw up their directions to the jury and a new trial is ordered.
Have you ever felt you didn’t get it right?
There isn’t a single trial where I thought, “Gosh, Moore, you nailed that one”. There are times you think, maybe I shouldn’t have said that to counsel. The Court of Appeal tipped me over in plenty of cases –and they were right, I was wrong.
What makes a good judge?
Never allow yourself to get angry and be respectful. No one goes to court because they want to be there, except for maybe some lawyers. For some, it’s the most traumatic thing that’s ever happened in their lives.
How can a judge make a difference?
You can give people a chance. I believe criminal offenders are not necessarily bad people. Most people who have made dreadful mistakes in their lives have not had the opportunities others of us have had.
You don’t get that chance as counsel to make submissions which recognise someone’s ability to rehabilitate. As a judge, it’s your decision, which is a very rewarding part of it and being able to resolve disputes.

As a father and grandfather, how hard was it to keep your emotions in check during the Grace Millane trial?
I was appalled at the complete misunderstanding of the so-called “rough sex” defence. It didn’t work in the end for Jesse Kempson, but it was an entirely legitimate defence, and it became personalised and weaponised. I became uncharacteristically angry.
Judges must have empathy, so you won’t be an effective judge if you aren’t empathetic. But empathy is different to sympathy. I went into the trial conscious that Grace Millane could have been my own daughter but that doesn’t stop you from approaching a task coolly and dispassionately.

At your valedictory, Ron Mansfield KC said it’s important for every judge to have tear ducts. Do you agree?
There have been times – though not often – as a prosecutor or as a judge, I felt I was in danger of losing it. I was conscious that if certain buttons were pressed, any visible emotion might be regarded as inappropriate.
If you well up with tears when you are about to sentence someone to 30 years’ non-parole imprisonment, what does that say about you? You must be professional. It is about compartmentalising. I have tools I rely on when I sense that emotion may intrude.
You can have tears privately, but never publicly.
You’ve covered many high-profile cases as a prosecutor and a judge: Joseph Thompson, Malcolm Rewa, Peter Plumley-Walker, the RSA murders, the Kahui twins, Antonie Dixon, Carmen Thomas, the Mark Lundy re-trial, Grace Millane – what case has stuck with you?

They would have to be child abuse and child murders; they are really upsetting. It was impossible not to be moved by Kahui.
There was also a young single mum whose house was invaded by a young burglar who chased her around into her bedroom. I went to the scene, I’m not going to describe it, but I had a young family then. Those are images which have remained.
You were appointed by the British Government as a public prosecutor to lead the historical sexual abuse trial in Pitcairn Island in 2004. There was an incident regarding a ritual crossing the dateline where images of you and Christine Gordon were photographed wearing plastic breasts and red wigs. Can you explain what happened?
It was a silly tradition, but I wasn’t going to be pompous and say, “No, I don’t do that sort of thing”, although I have to say I don’t dress up as much as I used to. The photos were taken and downloaded, and an islander associated with the defendants and anti the prosecution thought they would be useful to embarrass us.
What were you thinking?

I knew nothing about this; I was on holiday in northern Thailand and got a call from a lawyer who told me the media had these photos. I thought this could be embarrassing, and it has the potential to disrupt or adversely affect the process. I was worried but relieved by the reaction that I got from everyone who thought it was just excruciatingly funny.
My mother-in-law didn’t think it was funny. She was in England on holiday and saw the photo on the front page of the Independent. That was an awkward and worrying phase, but I think we handled it the right way. You front that stuff and say, “look, that was stupid, and we’re sorry”, we meant no offence. I don’t think it’s done me any harm in the long run.
How do I find that photo?
Google fake breasts. Red wig. Moore.

Speaking of wigs, Robin McCoubrey has previously joked about your hair landing you in awkward situations.
It has developed a momentum of its own. As a kid, I had nicknames that related to the colour of my hair. I was a “ginga”.
I was on my way back from doing charity work in the Solomons and was going through Australian immigration. I’m not sure if you feel this way, but I always feel like a criminal every time I go through immigration. I was looking at the camera, and nothing was happening. People were going past me on either side, I was getting anxious something was wrong. Then a sign popped up that said, “Remove your hat”. I thought, I’m not wearing a hat. Then this kind Australian immigration woman came over because I was looking around in a very self-conscious way.
She said, “Oh, I’m sorry, I’ll let you through, it sometimes does that with a toupee”.

How did you react?
I laughed. I couldn’t wait to tell my mates.
There was another incident with the late Sir Bob Jones at a restaurant, what happened?
I was meeting Sir Robert Jones for a business lunch the restaurant was full of lawyers and judges. Anyway, Sir Robert stood up as I approached the table and shouted in that penetrating voice, “Moore, you look ridiculous, take that stupid toupee off, it doesn’t fool anyone”. I turned bright red.
What’s your favourite TV show?
I don’t like crime shows, but I loved Boston Legal, it was like my law firm on steroids. You’ve got these different personalities, some people are insecure and overcompensate. Some are highly competent and smooth, then you’ve got the older partner who’s a little bit absent-minded. We had those, I was one.

You’ll love this, it’s a true story. My middle son Edward was studying at Otago when I gave a criminal lecture. He overheard two students talking about it later. One guy who missed it asked, “Who is he?” His friend said, “I don’t know, some bloke who is a cross between Donald Trump and Denny Crane”. It was pretty accurate, I thought.
What’s your favourite Denny Crane line?
“Don’t try getting into my head, son, there’s nothing in there.”
What advice would you give to your 16-year-old self?
That’s a cool question; I’ve thought about that. And I think the first one would be, “Grow up” and take a bit of responsibility. I get very embarrassed thinking back, how insensitive and immature I was.
Were you a ratbag? What was the worst thing you did as a teenager?
I’m not telling but it still embarrasses me how I treated people. I’m not saying I was a bully, but I was insensitive to people who I didn’t realise were sort of vulnerable at the time. I think I’ve made up for that, but ...

Do you have any regrets?
I wanted to be a doctor, but I failed, but there’s not much to regret. Sometimes I think my career may have compromised me being an effective parent, but my kids say, “No, dad you were always there when it mattered.”
What advice would you give to a young lawyer starting out?
Do what you enjoy, and you will succeed.
How would you like to be remembered?
As kind and moderately competent at the job. I would like people to think I’ve done a reasonably good job as a prosecutor and judge, and discharged those responsibilities with kindness and thoughtfulness.
Carolyne Meng-Yee is an Auckland-based investigative journalist who won Best Documentary at the Voyager Media Awards in 2022. She worked for the Herald on Sunday from 2007-2011 and rejoined the Herald in 2016 after working as an award-winning current affairs producer at TVNZ’s 60 Minutes, 20/20 and Sunday.
