R v Gray
[2025] NZHC 3250
•29 October 2025
IN THE HIGH COURT OF NEW ZEALAND PALMERSTON NORTH REGISTRY
I TE KŌTI MATUA O AOTEAROA TE PAPAIOEA ROHE
CRI-2024-054-681
[2025] NZHC 3250
THE KING v
GRAYSON GRAY
Hearing: 29 October 2025 Appearances:
G J C Carter for Crown
P J Drummond for Defendant
Sentencing notes:
29 October 2025
SENTENCING NOTES OF GWYN J
Introduction
[1] Mr Gray, you appear for sentence having pleaded guilty to a charge of aggravated robbery.1 The maximum penalty for the charge of aggravated robbery is 14 years’ imprisonment.
[2] As you recall, you came before me for a sentence indication in August of this year. As I indicated then, your sentence would need to take account of the fact that you are currently serving a sentence of imprisonment for other aggravated robberies, any guilty plea and your personal circumstances. In August, I indicated that if you were to plead guilty at that point, your sentence for aggravated robbery would be between two years and one month’s imprisonment and two years and three months’
1 Crimes Act 1961, ss 235(b) and 66(2).
R v GRAY [2025] NZHC 3250 [29 October 2025]
imprisonment depending on whether I received any evidence of remorse, and that that sentence would be served cumulatively on the sentence you are currently serving on other charges. You accepted that sentence indication and pleaded guilty.
[3] Since then I have received a letter, which Mr Drummond referred to, that you have written to Mr O’Rourke’s whānau, expressing your remorse. I will discuss that in more detail later.
[4] Although you will know the comments I made in my sentencing indication back in August, because this is a public process, I am going to repeat some of those comments today to explain how I have reached the final sentence. I will also describe the background factors that are relevant to the sentencing process.
[5] At this point I do want to explain to those of you in the public gallery that, as Mr Drummond mentioned and as I have said to Mr Gray, he asked for a sentence indication earlier this year. I gave a sentence indication and indicated that if he accepted it, unless anything changed substantively, that would be his sentence when I came to sentencing and he pleaded guilty on that basis. So when I refer to the sentencing indication that is what that means.
[6] In sentencing you today, Mr Gray, I apply a law called the Sentencing Act 2002, which sets out the purposes and principles of sentencing. The main purposes of sentencing in your case are to hold you accountable for the harm you have caused to Mr O’Rourke, and his whānau and to the community; to denounce your conduct; to deter you, and others, from committing the same kind of offending; to protect the community; and to assist in your rehabilitation and reintegration into society.2 The sentence I decide on has to mark the nature of your crime, but also to acknowledge who you are and your particular circumstances and background.
[7] I apologise again to those in the courtroom, but I do have to again recite the facts of what occurred. The charge to which you have pleaded guilty arises from an event in Palmerston North on 20 January 2024, in which the victim, Damon O’Rourke, was robbed of methamphetamine and then shot in the head.
2 Sentencing Act 2002, s 7.
[8] One of your co-defendants, Windsor Martin also pleaded guilty to aggravated robbery, before the trial and I sentenced him this morning.
[9] The other two co-defendants, Jaedyn Lovejoy and Tre McLean, were found guilty by a jury of manslaughter in Mr Lovejoy’s case and murder in Mr McLean’s case. Mr Lovejoy will be sentenced later today and Mr McLean in January.
Your offending
[10] I am now going to describe your role in what happened on 20 January 2024. You were the driver of a blue Mazda that you had borrowed from a friend. You picked up Mr McLean and Mr Lovejoy from Mr McLean’s address before picking up Mr Martin. Mr Martin then directed you where to drive to and at about 7.10 pm that evening, you and your three co-defendants travelled to a residential address in Palmerston North — Coromandel Court. When you got there, you and Mr Martin stayed in the car, while Mr McLean and Mr Lovejoy went into Mr O’Rourke’s sleep-out.
[11] Mr McLean was carrying a concealed cutdown firearm when they entered the sleep-out. He confronted Mr O’Rourke, demanding that he hand over a quantity of methamphetamine that he had stored in the room.
[12] Mr O’Rourke complied with their threats and handed over some methamphetamine. But they were not satisfied with what they had been given and continued to threaten him, insisting that more methamphetamine was hidden elsewhere in the sleep-out. At some point, Mr McLean discharged the firearm and Mr O’Rourke was shot once in the right side of his head. He died in the early hours of the next morning.
[13] When Mr McLean and Mr Lovejoy came out of the sleep-out several minutes later, you drove them and Mr Martin away and dropped them off around Palmerston North. And we have heard this morning from Mr Martin’s counsel, when he found out that the gun had been fired, he got out of the car at that point.
[14] On 21 January 2024, you purchased some petrol. At about 7.45 pm on the next day, you drove the Mazda off the road and out of sight and used the petrol to burn it. This left it extensively damaged and beyond repair, so that no forensic evidence could be obtained relating to the events of 20 January. You told the Police that you burned the car the best you could to “cover your arse”, and out of respect for the predicament your associate’s family were in.
[15] When you pleaded guilty to the charge of aggravated robbery, you accepted that you were the driver of the group to and from the Coromandel Court address, where you all had a common purpose to commit a robbery. You also accepted that there was a foreseeable possibility of harm being caused to the victim. You did not know about the firearm that Mr McLean had with him, and which was ultimately used to kill Mr O’Rourke.
Victim Impact Statements
[16] You will have heard the victim impact statements that Mr O’Rourke’s whānau read this morning. I do not propose to repeat them, and I know that you will have taken this yourself from what you heard, but I do want to emphasise the extent of the loss and pain that have been caused to Mr O’Rourke’s whānau, and that in part has been because of your actions.
Starting point
[17] I first need to set a starting point for your offending. Before I gave the sentencing indication, back in August, the Crown had said an appropriate starting point would be six years’ imprisonment. Your counsel, Mr Drummond, said four years would be appropriate. As you will recall, and as I will explain again today, I indicated that the appropriate starting point is four years and six months.
[18] In the sentencing indication I referred to what we call a guideline judgment for aggravated robbery called R v Mako.3 As the Court said in that case, “the range of conduct that can constitute aggravated robbery is very wide”.4 In its written
3 R v Mako [2000] 2 NZLR 170 (CA).
4 At [34].
submissions the Crown pointed to one scenario described in that judgment as being the most like your situation:5
[58] Forced entry to premises at night by a number of offenders seeking money, drugs or other property, violence against victims, where weapons are brandished even if no serious injuries are inflicted would require a starting point of seven years or more. Where a private house is entered the starting point would be increased under the home invasion provisions to around ten years.
[19] I considered the Mako case, but noted that direct comparison of the facts of each case with that scenario is no longer appropriate due to changes in the law since then, and that I should instead compare your case with other similar cases.6 I also considered a number of other cases that the Crown lawyer and your lawyer have referred me to,7 but I concluded that they were only of limited assistance for a number of reasons, including because of the minimal role that you played in the robbery itself compared to those other cases.
[20] I agreed with Mr Drummond, and the Crown conceded at the time, that a case called Dalrymple was more similar to your case and gives me greater assistance in setting a starting point for your sentence.8 In that case Ms Dalrymple was involved in a relationship with the principal offender, Mr McHugh. She drove Mr McHugh to the address, and he went into the address with the firearm and ammunition. She stayed in the vehicle. Mr McHugh demanded drugs and money from the intended victim, unaware that the victim had a visitor. Mr McHugh fatally shot the visitor in the head and escaped taking with him drugs and cash. Ms Dalrymple’s further role was to drive him away.9
[21] In that case the court assessed a starting point for Ms Dalrymple’s sentence at four years and six months:
[30] In order to assess your culpability I need to stand back and reflect on what it involved. First, it clearly involved the willingness to engage in a planned robbery of a house at night. It involved driving to a rural location to
5 At [58].
6 Tiori v R [2011] NZCA 355 at [16].
7 R v Royal [2009] NZCA 65 at [23]; and Karaitiana v R [2014] NZCA 126.
8 R v Dalrymple [2015] NZHC 2391.
9 At [3]–[10].
uplift a weapon. It then involved driving Mr McHugh back to the house where the robbery was to take place.
[31] The Crown submits that you must have known that the firearm was loaded or that Mr McHugh had ammunition in his possession. I do not consider that I can appropriately draw that inference. If the Crown had believed that it could prove that you knew of the existence of the ammunition, then no doubt it would have charged you as a party to Mr Witere’s murder because the killing of a human being was a clearly foreseeable consequence of an armed robbery involving a loaded firearm. The fact that the Crown never alleged that you had any criminal involvement in Mr Witere’s death means, in my view, that the Crown accepted that it could not prove that you knew the firearm was loaded. Nevertheless, there is no evidence to say categorically that you did not know it was loaded. The position therefore is that although you cannot be said to have known the firearm was loaded, you must have at least taken the risk that Mr McHugh had ammunition with him.
[32] I consider that your involvement in the ways that I have described mean that a significant sentence is required. It could certainly not be a sentence in the vicinity of three or so years, as I took your counsel to suggest. The fact that I have assessed Mr McHugh’s culpability as warranting a sentence of seven years imprisonment means that a significant adjustment is also required, however, to reflect the fact that he knew that he was taking a loaded weapon into the address with the probable intention of using it when you cannot be demonstrated to have had that knowledge.
[22] As Mr Drummond submitted at the sentencing indication, and Mr Vanderkolk accepted, the facts of your offending are very similar to those of Ms Dalrymple’s. Both of you were the driver for a robbery, where a loaded weapon was used by the principal offender and the victim died, but neither of you foresaw a risk of the victim dying.
[23] An obvious distinction between your case and Dalrymple is that you did not know your co-offenders had a firearm, whereas Ms Dalrymple did know that Mr McHugh had a gun but did not know he had ammunition for it. Mr Drummond at the time of the sentence indication submitted that in terms of the risk of harm and potential for serious violence, your culpability must be considerably less than Ms Dalrymple’s. Subject to the point I make below, I accepted that submission, and I also considered that you were less involved in the planning of the robbery than Ms Dalrymple appeared to be. You said at that time that you were there only because you were asked to “pick something up”. I did not have sufficient evidence before me to assess that assertion, but I accepted that you were roped into the robbery as the driver at the last minute, so you were not part of the planning, and it appears you did
not regularly associate with your co-offenders. That further reduces your culpability for the offending.
[24] I do note though on the other hand that two of your co-defendants were wearing their gang patches when they went into the sleep-out to commit the robbery, so you must have had an understanding of the potential for some level of violence. I also concluded that your burning out of the vehicle after the event was an aggravating feature of your offending. To some extent, it was, as you said, to “cover your arse” and because you were told to do it. But the fact is that you deliberately disposed of a vehicle used in the commission of an offence when you became aware of what had occurred, which meant no forensic evidence could be obtained relating to the events of 20 January.
[25] Balancing those factors against one another, I reached a conclusion in the sentencing indication that your level of culpability was, on the whole, similar to Ms Dalrymple’s. On that basis, I considered that a starting point of four years and six months’ imprisonment is appropriate.
Totality
[26] As I said in the sentencing indication, sentencing you for this offending is complicated by the fact that on 24 March 2025, you were sentenced in the District Court on two charges of aggravated robbery, as well as a charge of assault with intent to injure.10 That offending took place in December 2023, shortly before this offending. The District Court Judge gave you a starting point of five years’ imprisonment for that offending, and you are currently serving an end sentence of two years and nine months’ imprisonment.
[27] Sentences for separate offences can be applied either concurrently (which means served at the same time) or cumulatively (which means one after the other). I can impose a sentence of imprisonment cumulatively on a sentence you have already received.11 Because this offending that I am sentencing you for today and your
10 R v Gray [2025] NZDC 9109 [District Court sentencing notes].
11 Sentencing Act, s 83(1).
previous offending were not a connected series of offences, and you were on bail for the previous offending when you committed the current offending, I concluded that it was appropriate to treat them as cumulative sentences.12 That means that the sentence I impose today will be served once you complete your current sentence — that is, effectively added to it.
[28] In this situation, I have to go on to check that the total sentence for both that previous offending and this offending is not out of proportion to the seriousness of the offending. That is called the principle of totality.
[29] I indicated a starting point of four years and six months’ imprisonment for this offending. Your current sentence had a starting point of five years. Adding them together results in a total starting point of nine years and six months’ imprisonment for the total offending. In the sentence indication I considered that would be manifestly excessive and likely to result in a total period of imprisonment wholly out of proportion to its seriousness.13
[30] I considered that a total starting point of any more than eight years imprisonment would be out of proportion to the gravity of the overall offending. Obviously, I cannot reduce the starting point for the offending that you have been sentenced for in the District Court and nor can I impose part of the sentence for the same offence concurrently and part cumulatively. That means I must reduce the starting point of four years and six months to an adjusted starting point of three years, to have regard, as I said, to the principle of totality.
[31] On that basis, as I said I would in the sentence indication, I adopt an adjusted starting point of three years’ imprisonment.
[32] Having set the starting point, I then turn to what factors there are personal to you that might require an uplift (increase) or reduction to that starting point.
12 Section 84. Section 16(2) of the Sentencing (Reform) Amendment Act 2025, which amends s 84 of the Sentencing Act to provide further guidance on this point, does not apply to offences committed before it came into force on 29 June 2025. Regardless, I think a cumulative sentence is appropriate.
13 Sentencing Act, s 85(2).
Aggravating factors - offending while on bail
[33] As I have mentioned, this offending took place while you were on bail for two charges of aggravated robbery, committed in December 2023. Both Mr Drummond and the Crown agreed that that is an aggravating factor which requires an uplift to the starting point.
[34] At the sentencing indication the Crown said I should adopt a “stern” approach in this case, given how connected in time and circumstances this offending was to your December 2023 offending. The Crown said an uplift of between six and 12 months would be appropriate.
[35] Mr Drummond however said six months was a sufficient uplift. His submission was that, when adjusting for totality, I have already taken account your previous aggravated robberies, and that a 12 month uplift would be disproportionate. I did not accept that first submission — an uplift for offending while on bail is not an additional punishment for the offending for which you were bailed, but a reflection of your disregard for court processes and orders.14 But I did agree that a 12 month uplift would be disproportionate and I adopted an uplift, or increase, of six months from the starting point for your offending while on bail.
Mitigating factors
Guilty plea
[36] Then there are factors that mean I should reduce that starting point, what we call mitigating factors. The first is the fact that you pleaded guilty. Your counsel, Mr Drummond sought the full available allowance for a guilty plea, and that is 25 per cent and the Crown accepted that full credit would be appropriate.
[37] You were originally charged with murder; that charge was reduced to manslaughter and then reduced to aggravated robbery. You sought a sentence indication on the same day that the last change in charge occurred. After receiving my
14 Clunie v R [2013] NZCA 110 at [22].
indication, you pleaded guilty, which was at the first available opportunity. I agreed that the full 25 per cent discount for guilty plea was appropriate.
Personal factors
[38] In the District Court, you received a 15 per cent discount for personal factors, including the violence, abuse, loss and substance abuse during your upbringing, and the impact of gang connections, methamphetamine use and mental health issues as you grew older.15 Mr Drummond sought the same discount for this offending, and the Crown indicated that it would not take issue with a similar allowance.
[39] Since then I have read the two Provision of Advice to Courts (PAC) reports from 28 February 2025 and 14 October 2025, and your Hōkai Tapuawae Report dated 24 November 2024. I want to talk a little about what is in those reports. I acknowledge that much of the information is personal information and I certainly won’t read out all of that personal information, but I need to discuss how it impacts on your sentence.
[40] You whakapapa to Te Atiawa in Taranaki and Ngāti Haupoto. You were born and raised in Palmerston North, in the Highbury area. Your household was drug-fuelled and abusive. As the oldest sibling in the house, you did your best to look after your younger siblings. At around age eleven your father passed away, and you suffered from unresolved grief. You have also dealt with the deaths of other close family members.
[41] You found school difficult and believe that you have undiagnosed ADHD. You were expelled from high school for fighting and smoking cannabis on school grounds. You attended alternative education programmes in Christchurch. On returning to Palmerston North, you found employment in forestry and roofing. You speak very highly of your former manager, Mr Wilkinson, and he speaks very highly of you. Unfortunately, you still had two weeks left of your three-year apprenticeship when you were arrested. Mr Wilkinson says that you have “huge potential” and a high degree of work ethic, and it is possible that you will work together again after you have completed your sentence.
15 District Court sentencing notes, above n 10, at [4]–[12].
[42] You have two young daughters and expressed to the report writer that you believe in a God or Atua and your mum has been your spiritual support. You likely have depression and anxiety.
[43] You started using drugs at a young age, and methamphetamine has been present for most of your life. You are at high risk, the report writer says, of abusing alcohol, cannabis and methamphetamine, which could of course lead to health, social, legal or financial issues. You have expressed interest in completing an alcohol and drug treatment programme during time you spend in prison.
[44] You are not affiliated to or actively involved with any gang. Many of your associates have connections to criminal groups, but you report that you knew them prior to their activity in this way. On the day of the offending, you report that you had used some cannabis and that, to quote you your “mind was a mess” due to an ongoing relationship separation. You felt compelled to provide your co-offenders with transport, but on reflection say you should have been more assertive in saying no.
[45] I can clearly see the causative effect your background will have had on your offending, and it has been useful for the court to have those further reports. Having considered the reports further, I will grant a discount of 15 per cent for personal factors.
Remorse
[46] In the District Court, you also received a five per cent discount for remorse, although it appears that Judge Northwood focused his analysis on this point on the impact of imprisonment on your children.16 At the sentence indication Mr Drummond invited me to apply the same discount for remorse to this offending. At that time, I said that just because you have shown remorse for other aggravated robberies, that does not mean that you have shown remorse for your involvement in this offending. Remorse must inherently relate to the specific case in a way that personal background factors do not. I said I would require specific evidence from you on your remorse for this offending, at sentencing, in order for me to consider whether such a discount is warranted.
16 At [13]–[14].
[47] I now have the benefit of the updated PAC Report of 14 October 2025 which says:
Mr Gray stated that he had a lot of regret and upset for the impacts his role in the offending has caused. Mr Gray acknowledge the extent of the impacts on family and children and wished to express a written from of remorse by way of letter he has reportedly submitted to his legal counsel. Being the biggest regret (in his life) Mr Gray stated that he should have just said no to them and avoided the entire situation altogether.
Mr Gray detailed a deep depression spiral when he was remanded in custody and found it difficult to emotionally cope with the stress, guilt and upset he was experiencing as a result of his actions.
[48] I have also received a copy of the letter referred to in the PAC Report which you have written to Mr O’Rourke’s whānau, and I hope that they have received that letter too. In that letter you say that you express your deepest condolences to the whānau and acknowledge the trauma involved for all of them and particularly the children of the family. You say that you will forever regret the choices you made that day and will always live with the shame and guilt. You hope that they may ultimately forgive you and say that you will work towards being the best person you can be.
[49] I accept that you are genuinely remorseful for the harm you have caused by your actions and will grant a small discount of five per cent to reflect that remorse.
End sentence
[50]In summary, I impose:
(a)a starting point of three years’ imprisonment, adjusted for totality;
(b)an uplift of six months for offending while on bail;
(c)a guilty plea discount of 25 per cent (nine months);
(d)further discounts of 20 per cent (eight months, rounded up);
(e)arriving at an end sentence of two years and one month’s imprisonment, to be served cumulatively on your current sentence.
Sentence
[51]Grayson Taikoi Gray, please stand.
[52] On one charge of aggravated robbery, I sentence you to two years and one month’s imprisonment.
[53]You may stand down, thank you Mr Gray.
Gwyn J
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