Castillano v The King

[2025] NZHC 1854

IN THE HIGH COURT OF NEW ZEALAND AUCKLAND REGISTRY

I TE KŌTI MATUA O AOTEAROA TĀMAKI MAKAURAU ROHE

CRI-2024-404-336

[2025] NZHC 1854

BETWEEN

ANTONIO CASTILLANO

Appellant

AND

THE KING

Respondent

Hearing:	30 June 2025
Appearances:	M W Ryan for Appellant R N Benic for Respondent
Judgment:	9 July 2025

JUDGMENT OF WILKINSON-SMITH J

This judgment was delivered by me on 09 July 2025 at 10 am.

………………………… Registrar/Deputy Registrar

Solicitors/Counsel:
M W Ryan, Auckland

Meredith Connell, Auckland

CASTILLANO v R [2025] NZHC 1854 [9 July 2025]

Introduction

[1]    Antonio Castillano appeals an end sentence of four years and two months’ imprisonment,1 following guilty pleas to charges of:

(a)criminal harassment (x 9);2

(b)causing harm by posting digital communication;3 and

(c)obtaining by deception (representative).4

[2]    Mr Castillano initially sought to appeal both conviction and sentence. The conviction appeal has since been abandoned — Mr Castillano now solely seeks to appeal his sentence on the basis it is manifestly excessive.

The offending

[3]    Mr Castillano has an extensive number of aliases. His offending was conducted through numerous Facebook accounts in various names, which he utilised to harass the victims.

Victim ‘M’

[4]    In August 2020, Mr Castillano met the first victim M through Tinder and began messaging  her.  When  the  contact  graduated  to  video  chat,  M  realised  that   Mr Castillano was not the person depicted in his profile picture. M had mentioned to Mr Castillano that she was renting out a carpark at her apartment and Mr Castillano expressed an interest. M met Mr Castillano at her apartment to view the carpark. Ultimately, she decided not to rent the carpark to him as she did not feel comfortable around him.

[5]    Between August 2020 and August 2021, Mr Castillano engaged in a harassing pattern of behaviour toward M. This involved sending M multiple Facebook friend

1      R v Castillano [2024] NZDC 14915.

2      Harassment Act 1997, s 8(1)(b). Maximum penalty: two years’ imprisonment.

3      Harmful Digital Communications Act 2015, s 22. Maximum penalty: two years’ imprisonment.

4      Crimes Act 1961, ss 240(1)(a) and (a). Maximum penalty: seven years’ imprisonment.

requests from multiple accounts, as well as her mother. After M asked Mr Castillano to stop, he began sending M upwards of 10 requests every day from various accounts.

[6]    On 1 September 2020, Mr Castillano then sent M a message accompanied by screenshots of a Facebook post which contained M’s name, photograph, phone number, address and falsely advertising that she was a prostitute. M was contacted multiple times enquiring after sexual services as a result.

[7]    On 22 September 2020, M noticed Mr Castillano was outside her home and taking photos using a wide lens camera for several hours. Over the next few months, M also observed Mr Castillano lurking around her address and taking photographs with his phone.

[8]    Between March and April 2021, Mr Castillano entered M’s apartment building and slipped four handwritten notes under her door. The notes were all threatening in nature and continued to falsely accuse M of being a prostitute. They included a note saying, “I will get you in the end”.

[9]    On 25 November 2022, Mr Castillano sent M a video which depicted him masturbating. Around the same time, he stood outside M’s apartment and yelled at her “you fucking stuck up whore”.

Victim ‘K’

[10]   Around April 2020, K accepted a Facebook friend request from Mr Castillano who was using the name Glen Green. Mr Castillano then messaged K saying that a friend of hers had said that she was a prostitute. K blocked Mr Castillano on Facebook. She then began receiving hate mail from numerous Facebook profiles operated by Mr Castillano. The messages claimed that she was a paedophile and made death threats against her. They also included pictures of her.

[11]   The harassment continued between April 2020 until February 2023 and only ended after K contacted the police.

Victim ‘D’

[12]   D is a friend of the first complainant M. After D tagged M in a Facebook post, she started receiving numerous messages from various Facebook profiles under the control of Mr Castillano. The messages were abusive, accusing D of being a prostitute.

[13]   On 25 November 2022, Mr Castellano sent D a video of himself masturbating, accompanied by a message which read, “thinking about sexy u”.

Victim ‘G’

[14]   On 20 December 2022, G commented on a Facebook post made by a friend who had received unsolicited and unpleasant messages. Later that day, G received a message request from a Facebook profile controlled by Mr Castillano with a message that said, “watch you’re back pedo”.

[15]   G received multiple further messages from Facebook profiles controlled by Mr Castillano, including death threats and  messages  telling  her  to  kill  herself.  Mr Castillano made public posts calling G a child molester, a “transvestite freak” and calling for vigilante action against her.

Victim ‘R’

[16]   On 21 December 2022, Mr Castillano sent R a screenshot of a Facebook post which included a picture of R and her children and an allegation that she was a child sex predator.

[17]   Mr Castillano subsequently sent R a Facebook message saying, “U r gorgeous”.

Victim’ T’

[18]   On 7 January, T received an unsolicited message from a Facebook account operated by Mr Castillano which read, “Look out dyke, people are watching you”. Two further abusive messages were sent the following day.

Victim ‘N’

[19]   On 8 January 2023, N received two messages from Facebook accounts operated by Mr Castillano. Both messages read, “Someone put u all over FB for raping kids u freak dyke cunt. Hope u get vigilante justice”.

Obtaining by deception

[20]   Between 22 January 2020 and 21 February 2021, Mr Castillano applied for and was granted a jobseeker benefit, despite an existing grant from WINZ. He utilised a fake name and fake documents, such as a false tenancy letter, to support his fraudulent application. Mr Castillano also received other supplements such as the accommodation supplement and temporary additional support. Mr Castillano was overpaid by WINZ to the sum of $20,216.

The sentencing decision

[21]   Mr Castillano sought a sentence indication. On 9 February 2024, Judge Jelaš delivered the following indication:

(a)A starting point of three years’ imprisonment for the offending against M and K.

(b)An uplift of six months for the offending against the remaining complainants and the harmful digital communications charge.

(c)A further uplift of 10 months for the obtaining by deception charge, bringing the starting point to four years and four months’ imprisonment.

(d)A 20 per cent credit for guilty pleas.

(e)An uplift of 15 per cent (six months) for Mr Castillano’s history of similar offending.

(f)An end sentence of three years and 11 months’ imprisonment.

[22]   Mr Castillano did not accept the indication but pleaded guilty not long after the sentence indication hearing, which was close in time to his scheduled trial.

[23]   The Judge adopted the three-year starting point as indicated for the offending against M and K. Counsel for Mr Castillano sought a reduction in the indicated uplift for the offending against the remaining victims as two charges were not pursued. However, with the benefit of the victim impact statements, and because the sentence indication no longer applied, the Judge reconsidered the appropriate uplift. She said that Mr Castillano’s offending was a “lengthy campaign of terror” against people with whom he had no prior contact, with the exception of one victim. The Judge considered that a 10-month uplift was appropriate for the offending against the five additional victims.

[24]   A 10-month uplift for the obtaining by deception charge was also applied. This resulted in an adjusted starting point of 56 months’ imprisonment.

[25]   The Judge also reconsidered the guilty plea discount. The Judge said that a  20 per cent discount was appropriate for the fraud charge. However, the situation was different for the criminal harassment charges. The guilty pleas were entered on the morning of trial and the Crown still expended resources in preparing for trial. The Crown case was overwhelming and propensity evidence was available. The prospect of trial would have been daunting for the victims. Accordingly, only a five per cent credit was available for these late pleas.

[26]   The Judge was invited to consider a discrete discount for remorse. However, she did not find this appropriate for remorse expressed after pleas of guilty on the morning of the trial. The Judge also declined to allow a discount for rehabilitative steps which were unlikely to have any significant effect on future risk.

[27]   The Judge accepted that Mr Castillano suffered significant disadvantage in his upbringing. In his later teenage years, he was in state care which was not a protective environment. His schooling years were disrupted by his behaviour, and he exited schooling early; he also found it difficult to remain in employment. Mr Castillano first

appeared before the Court in 1985. The Judge characterised Mr Castillano as someone who was “trapped in the criminal justice pipeline”.

[28]   However, the Judge was not satisfied that there was a causative link between this personal history and the offending, particularly the harassment charges. There were suggestions of a previous diagnosis of a psychiatric disorder, but this was not verified. Accordingly, the Judge allowed a 10 per cent discount for Mr Castillano’s difficult background.

[29]   The total reduction for personal factors was 15 per cent or eight and a half months. The Judge further reduced the sentence by one and a half months to recognise the indicated 20 per cent discount for the guilty plea on the fraud charge. That led to an end sentence of 46 months’ imprisonment.

[30]   The final step in the sentencing process was to increase the end sentence due to Mr Castillano’s significant criminal history. Mr Castillano has a history of similar behaviour towards women. A four-month uplift was imposed for previous convictions of breaching a protection order, criminal harassment and misuse of a telephone (inferred to be a harassment-type offence). Mr Castillano was also last sentenced for criminal harassment in 2015 and for causing harm by posting a digital communication in 2021. This resulted in an end sentence of 50 months’ or four years and two months’ imprisonment.

The approach on sentence appeals

[31]   An appellant may appeal against sentence as of right under s 244 of the Criminal Procedure 2011.

[32]   An appeal against sentence must be allowed if an appellate court is satisfied that for any reason there is an error in the sentence imposed and that a different sentence should be imposed.5 In any other case, the appellate court must dismiss the appeal.6 Sentencing is not a science, and an appellate court will not intervene unless

5      Criminal Procedure Act 2011, s 250(2).

6      Section 250(3).

the end sentence is outside the range available to the sentencing judge.7 An appellate decision is focused on the end result rather than the process by which the sentence was reached.8

[33]   When allowing an appeal on the basis that there was an error in the sentence imposed, the appellate court may: set aside the sentence and impose another sentence (whether more or less severe) that it considers appropriate; vary the sentence or any part of the sentence or any condition of sentence; or remit the sentence to the court that imposed it.

[34]   The appellate court does not start afresh or simply substitute its own opinion for that of the sentencing judge. Rather, it must be shown that there was an error, whether intrinsically or because of additional material submitted on appeal.9 The court will not intervene where a sentence imposed is within a range that could be properly justified by accepted sentencing principles.10

Submissions

[35]Counsel for Mr Castillano advanced four grounds of appeal:

(a)Taking into account the principle of totality, the uplifts for the other harassment charges and the obtaining charge were excessive. An uplift of no more than six months’ imprisonment for each type of offending (for a total of 12 months) should have been applied.

(b)The guilty plea discount was inadequate.

(c)A discount of five per cent should have been applied for remorse. Further, Mr Castillano had made rehabilitative efforts in custody, developing a safety plan and completing nine different courses which should be recognised by way of discount.

7      Palmer v R [2016] NZCA 541 at [17]; and Tutakangahau v R [2014] NZCA 279, [2014] 3 NZLR 482.

8      Kumar v R [2015] NZCA 460 at [81].

9      R v Shipton [2007] 2 NZLR 218 (CA) at [139].

10     Tutakangahau v R, above n 7, at [30].

(d)A discount of 15 to 20 per cent should have been allowed for background factors. Mr Ryan submitted that the information in the PAC report as provided to the Judge sufficiently justified this greater discount. Mr Castillano’s Abuse in Care Supported Assessment Report admitted on appeal confirmed he meets the criteria for certain psychiatric disorders and supports a causative connection between his background and the offending.

[36]   The appellant accepted that the starting point of three years’ imprisonment for the offending against M and K was within range. Issue was taken with the 10-month uplift for the charges involving the five further victims.

[37]   It was submitted that Mr Castillano’s end sentence should be adjusted on appeal as follows:

(a)a starting point of three years’ imprisonment for the lead harassment offending;

(b)an uplift of six months for the balance of the harassment offending;

(c)an uplift of six months for the dishonesty offending;

(d)a discount of 15–20 per cent for guilty pleas;

(e)a discount of five per cent for remorse and rehabilitation;

(f)a discount of 15–20 per cent for personal background factors; and

(g)an uplift of four months for previous criminal history.

[38]   The Crown submitted that the sentence was not manifestly excessive. A higher overall starting point was available — the Court of Appeal has previously found it appropriate to impose cumulative sentences for criminal harassment against multiple

victims, recognising the offending was individual despite occurring over the same period.11

[39]   The Crown noted that a two-year starting point would have been available for the fraud charge on a standalone basis.12 The Crown submitted it was difficult to see how this could be justifiably reduced to six months for totality.

[40]   The Crown disputed that a discrete discount for remorse was warranted and says any discount for rehabilitation must be viewed in the context of repeated similar offending over the course of decades.

[41]   The Crown also submitted that the 10 per cent afforded for personal background factors was appropriate when viewed in  the  overall  circumstances.  The Crown accepted that Mr Castillano’s mental health issues inform the underlying psychology of his offending. However, any reduction must be balanced with the need to protect public safety. The credits for personal mitigating factors were granted with reference to the significant need to protect the community from this type of offending. The  Crown  position  was  that  a  lenient  starting  point  and  modest  uplift  for   Mr Castillano’s previous criminal history balanced any additional credit that might be warranted based on additional material filed on appeal.

Discussion

[42]   The offending in this case took place against seven different victims between August 2020 and January 2023. Two of the victims  were recipients  of  videos of  Mr Castillano masturbating. The contact with the victims included not only abusive or sexually suggestive messaging but also, in some cases, threats of harm.

[43]   The offending also occurred against an extensive background of like offending. Mr Castillano was convicted in 2021 for similar offending, but he was already offending against victim M and he continued over the next three years to offend against

11 Butler v R [2019] NZCA 65 at [17]; and Nottingham v R [2019] NZCA 344 at [99].

12 Ministry of Social Development v Albert [2015] NZHC 1288; Williamson v Police [2016] NZHC 520; and Ministry of Social Development v Proctor DC Palmerston North CRI-2012-054-947,  10 August 2012.

the other victims of the present offending. It is clear that Mr Castillano is a recidivist offender who was undeterred by previous sentences or by prosecution in 2021.

[44]   I accept the Crown’s submission that it would have been open to the Court to impose cumulative sentences in respect of each victim, based on the approach taken by the Court of Appeal.

[45]   The Crown analysis of the relevant authorities and the starting points available for the offending against each individual victim was not seriously challenged. On  the Crown analysis, a combined starting point of 75 months’ imprisonment was available if each offence were dealt with as a separate matter. Of course, that would have had to be adjusted for totality, but even with a totality adjustment of 20 per cent which the Crown submits would have been appropriate, a starting point of 60 months or five years’ imprisonment was potentially available. The starting point imposed was effectively 18 months in respect of M and K, but only a further two months in respect of each additional victim. On any analysis, that is well within range and could not be described as manifestly excessive.

[46]   The appellant takes issue with the fact that the Judge revisited the uplift following the lapse of the sentence indication. The reality is that Mr Castillano chose not to accept the sentence indication. That sentence indication therefore became largely irrelevant. It was open to the Judge to review and reconsider the uplift, particularly in light of the victim impact statements that she received. The additional uplift for the charge of obtaining by deception relates to quite separate offending. In isolation, I agree that a starting point in the vicinity of two years’ imprisonment would have been available for the fraud offending. That sentence also had to be reduced for totality, but it was reduced by over 50 per cent from an available starting point of two years.

[47]   The appellant takes issue with the level of discounts applied. The appellant seeks a reduction of 15 to 20 per cent for guilty plea, on the basis that the guilty pleas obviated the need for a jury trial and for the complainants to give evidence. That is, however, always the case when a guilty plea is entered, even on the eve of trial. A

15 to 20 per cent discount is not usual for a plea entered at a very late stage, even though it inevitably means that a trial is not required.

[48]   In this case, guilty pleas were entered on the morning of trial. A discount of five per cent in such circumstances is unremarkable. The Judge applied a further discount of one and a half months to acknowledge a larger available guilty plea discount for the fraud charge. As discussed with counsel during the hearing, a better approach to differentiate between guilty plea discounts for different charges (or for pleas entered at different stages) would be to identify the starting point for each charge and apply the discount as a percentage to that starting point, before considering totality as a final step in the sentencing process. But that is a counsel of perfection, and the real issue is whether the guilty plea discount was within the appropriate range and the end sentence not manifestly excessive.

[49]   The overall guilty plea discount applied was in the vicinity of eight per cent. The fraud charge which the Judge said attracted a 20 per cent guilty plea discount represented only about 20 per cent of the overall sentence. The other 80 per cent of the sentence attracted only a five per cent discount. The additional three per cent recognises that the charge which attracted the higher guilty plea discount was a relatively small part of the overall offending.

[50]   I turn now to the various credits that the appellant submits should have been applied. The first concerns remorse and rehabilitation.

[51]   When considering discounts or credits, it is important to consider the principles and purposes of sentencing. Any credit must be consistent with those principles and purposes. The sentencing process must fulfil a number of functions. There must be a punitive element. That is reflected in the purpose in s 7(1)(a), to hold the offender accountable for harm  done  to  the  victim  and  the  community  by  the  offending; s 7(1)(b), to promote in the offender a sense of responsibility for and acknowledgment of that harm; and s 7(1)(c), to provide for the interests of the victim of the offending. The punitive element of sentencing recognises that a victim is not entitled to take vigilante action themselves and must rely on the state to punish the offending. The

punitive element is also reflected in the purposes of denunciation and deterrence. Sentencing must protect the community from the offender.

[52]   Sentencing must also assist in the offender’s rehabilitation and reintegration. Remorse and rehabilitation are properly recognised because a person who is genuinely remorseful and who undertakes rehabilitation is assumed to pose less of a danger to the community. The risk of reoffending is assumed to be reduced. A credit for remorse or rehabilitation is difficult to justify when the corresponding lowered risk of further offending is simply not apparent on the facts of the case, despite protestations of remorse or apparent efforts at rehabilitation. It is not enough for an offender to go through the motions. A reduction for remorse and rehabilitation is related to a resultant reduction in culpability and future risk. Mr Castillano’s prospects of rehabilitation are problematic. The available reports suggest that any rehabilitation will require a significant period of time to be effective and, in the meantime, Mr Castillano continues to pose a danger.

[53]   A reduction for difficult personal circumstances is different. It is not related to lower future risk, but to lower culpability. It recognises that some people, because of their background, are more vulnerable through no real fault of their own to becoming involved in the criminal justice system. The punitive element of the sentencing is reduced because the offender’s culpability is reduced. These reductions can come into conflict with the need to protect the public. The person who has been disadvantaged, institutionalised or habituated to criminal offending may be less culpable but may nevertheless pose a very extreme risk. At some point, that tension means that discounts for personal factors must be reduced in the interests of public safety.

[54]    In the present case, the sentencing Judge found Mr Castillano’s expressions of remorse and efforts at rehabilitation somewhat hollow in light of his history. I agree with the Judge’s assessment. Mr Castillano professed remorse against a background of almost continuous recidivist offending. He professed a willingness to engage in rehabilitation despite having been previously sentenced for similar offending and advised of the likely consequences of continuing such offending. In a previous sentencing decision, Allan J warned Mr Castillano that “the public is entitled to be

protected from him and he himself must learn from the imposition of ever-increasing penalties that his behaviour will not be tolerated”.13

[55]   The appellant complains that the District Court provided an inadequate reduction for his personal circumstances on the basis there was no evidence of a causative link. Evidence in the form of an ACC report was provided on appeal without objection from the Crown. The report adds somewhat to the relatively extensive information before the sentencing Judge, being a s 27 report and a PAC report setting out Mr Castillano’s difficult background.

[56]   The appellant says that the ACC report confirms Mr Castillano’s psychiatric issues. In fact, the ACC report is something of a double-edged sword and feeds into the tension I referred to earlier. While it does indicate that Mr Castillano has psychiatric issues, it also refers to an anti-social personality disorder, gang connections and a high risk of recidivist offending, coupled with a lack of insight and lack of empathy.  Those  factors  tend  to   confirm   the  sentencing   Judge’s   view  that   Mr Castillano’s personal difficulties must give way to the need to protect the public. The report, in my view, is consistent with such a need. The recidivist offending has continued and, if anything, escalated.

[57]   The Crown submitted that the uplift for Mr Castillano’s previous history was modest.   Mr Castillano has  a significant  history of previous  criminal offending.   In 2021, he was convicted of causing harm by  posting a digital communication.     In 2020, he was convicted of behaving threateningly and of a representative charge of blackmail. He has previously been convicted of criminal harassment in 2016, 2012 and 2008. He has numerous convictions for contravening a protection order. His criminal offending spans the period of 1985 until the present day, running through many pages and amounting to almost 200 convictions. There are also numerous dishonesty convictions. Accordingly, I find that the uplift of four months for the previous history was modest and could have been higher.

[58]   Ultimately, whether a sentence could have been constructed differently is not the issue on appeal. This Court will only interfere where the end sentenced imposed

13     Green v Police [2012] NZHC 3228 at [30].

was manifestly excessive. I do not find that to be the case here. In my view, the Judge imposed the least restrictive sentence available. A higher starting point could have been justified and a greater increase for previous convictions and quick recidivism, given that the current offending commenced within a year of sentencing for similar offending. I do not find any error in the discounts applied but, in any event, the end sentence is within range.

Result

[59]The appeal is dismissed.

Wilkinson-Smith J