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[2026] NSWCA 109
procedural. Order 3 of Nixon J’s orders was stayed pending final determination of the appeal or further order, conditional on Keybridge giving the usual undertaking as to damages. The appeal was expedited and...
The Court of Appeal treated the three challenged orders separately. It considered Keybridge’s appeal sufficiently arguable for a stay application, but did not decide whether Keybridge would win the appeal. The immediate transfer of money under order 3 was stayed because of the risk that Keybridge might have difficulty recovering it if it later succeeded. Orders 5 and 7 were not stayed: order 5 mattered to Mr Bolton’s ability to prepare for a trial due to start shortly after the appeal hearing, while no evidence showed that order 7 would require payment before the appeal was decided.
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3 cited instruments linked from this judgment.
2,239 words · generated 07/10/2026
This was an interlocutory decision of the NSW Court of Appeal on Keybridge Capital Limited’s application to stay selected orders made by Nixon J while Keybridge appealed the underlying decisions. Stern JA heard the motion on 9 June 2026 and gave reasons for the orders made that day. The appeal was fixed for hearing on 18 June 2026, with a half-day estimate ([6]).
Nixon J’s first decision gave the substantive conclusions about Mr Bolton’s claim under a Director’s Deed. His second decision, Bolton v Keybridge Capital Limited (No 2) [2026] NSWSC 604, made the orders reflecting those conclusions ([1]). Order 1 declared that cl 3.1 required Keybridge to pay specified legal costs for Mr Bolton’s defence of proceedings in New South Wales and Italy as they were incurred. The declaration preserved a right for Keybridge to recover payments if it was later established that Mr Bolton was not entitled to indemnity for them ([8]–[9]).
Keybridge did not seek to stay that declaration. Its motion concerned three consequential orders: order 3, requiring an immediate transfer of $210,839.38 and €80,026.96 to a solicitors’ trust account; order 5, setting time limits for later payments of costs incurred; and order 7, requiring payment of the costs of Mr Bolton’s indemnity proceeding on the ordinary basis, as agreed or assessed ([12]).
Keybridge argued that its appeal raised serious issues about the construction of cl 3.1 and the scope of the deed, including the relationship between clauses 3.1, 3.3 and 3.4 and the statutory restrictions in s 199A of the Corporations Act 2001 (Cth) ([11], [56]). It also argued that payments made before the appeal could be difficult or impossible to recover if it succeeded. Mr Bolton opposed a stay, saying it would impair his ability to fund legal representation, particularly for NSW proceedings due to begin on 23 June ([45]–[53]).
Stern JA made a divided order. Order 3 was stayed, conditional on Keybridge giving the usual undertaking as to damages. Orders 5 and 7 were not stayed. The motion was otherwise dismissed, and its costs were made costs in the appeal ([6]–[7], [64]).
The Court applied the established stay framework. An applicant must show a serious issue for the appeal and a real risk of prejudice or damage if the stay is refused. If those matters are established, the Court weighs the balance of convenience and the parties’ competing rights ([40]). The overriding consideration is the interests of justice, and the statutory power under s 135 of the Civil Procedure Act 2005 (NSW) must be exercised judicially and consistently with the Act, including s 56 ([39]).
The Court made only a preliminary assessment of the appeal. It did not determine the strength of Keybridge’s case in detail. It concluded that the questions about the proper construction and scope of the Director’s Deed were substantive legal issues that could not be dismissed as having no reasonable prospects ([56]). That conclusion met the serious-issue aspect of the stay analysis, but was not a ruling on the ultimate appeal.
The practical consequences differed between the three orders. For order 3, the Court accepted that the payment was substantial and that some of the money would be paid to solicitors in Italy and some to Hamilton Locke ([58]). If Keybridge succeeded on appeal, any repayment order would have to be made against Mr Bolton. The Court was satisfied that he did not then have money available to repay the sums and that it was uncertain when, or whether, funds would become available ([59]). That created material prejudice to Keybridge if the payment went ahead.
The Court also examined the alleged prejudice to Mr Bolton. It was not satisfied that staying order 3 would materially affect his ability to obtain representation for either the NSW proceedings or the appeal ([60]). In reaching that view, Stern JA had considered evidence about Hamilton Locke’s departure from the NSW proceedings and Mr Bolton’s access to counsel for the appeal ([29]–[37]). The balance therefore favoured staying order 3.
Order 5 presented a different balance. The NSW trial was set to start on 23 June, only five days after the appeal hearing. Stern JA inferred that a stay of order 5 would create a significant risk to Mr Bolton’s ability to obtain representation for that trial ([61]). The suggestion that he could apply to vacate the trial date did not adequately answer that concern, particularly given that the hearing had been listed in March and involved multiple parties. The expected prompt determination of the appeal and the provision for payment within three business days of costs being incurred reduced, but did not eliminate, the prejudice to Keybridge. The balance did not support a stay of order 5 ([61], [63]).
Order 7 was different again. It concerned ordinary-basis costs of the indemnity proceeding, to be agreed or assessed. There was no evidence that this process, or any resulting payment, would take place before the appeal was determined. The Court therefore found no relevant prejudice to Keybridge from leaving order 7 unstayed ([62]–[63]).
The judgment presents the governing principles as settled, rather than announcing a new general test. It adopts the framework summarised in Michael Hill Jeweller (Australia) Pty Ltd v Gispac Pty Ltd [2024] NSWCA 128 at [5]: a serious issue, a real risk of prejudice or damage, and then a balance of convenience taking account of competing rights ([40]). The Court also referred to the interests of justice as the overriding principle ([39]).
On the appeal’s merits, Stern JA relied on the established caution that a stay court will not ordinarily speculate about the appeal’s strength, while retaining the ability to exclude an appeal with no real prospect of success brought merely to gain time ([41]). The decision’s practical contribution is its application of that cautious approach to an expedited appeal involving three distinct payment orders.
The judgment also treated the risk of non-repayment as capable of being material even though the orders were not an award of damages or restitution. The Court considered Port Macquarie-Hastings Council v Diveva Pty Limited [2017] NSWCA 4 and Woolworths Ltd v Strong (No 2) (2011) 80 NSWLR 445 relevant because they recognised the significance of difficulty or delay in recovering money if an appeal succeeds ([42]–[43]). The Court expressly cautioned that this factor is not determinative by itself; it is one matter in the interests-of-justice assessment ([43]).
The decision’s order-specific approach is important. It did not treat the existence of an arguable appeal, or the risk attached to one payment, as automatically determining the status of every related order. Instead, it assessed the consequences of staying immediate payment, later-incurred payments, and ordinary-basis costs separately ([57]–[63]). The judgment therefore illustrates the application of the established framework to different forms and timings of payment. It does not establish that one category of payment must always be stayed or left in force.
At [39], Stern JA states: “The overriding principle is the interests of justice.” In plain English, the Court’s task was not simply to protect the appellant or preserve the result below. It had to evaluate the practical consequences for both sides and the justice of the interim position.
At [56], the Court says the appeal raises “a serious issue to be tried.” This means Keybridge’s arguments about the Director’s Deed were not so insubstantial that the Court could disregard them at the stay stage. It does not mean that Keybridge had won, or that the appeal would succeed.
At [59], the Court explains that Mr Bolton lacked funds then available to repay the payment and that it was uncertain when, or potentially whether, money would become available. This finding addressed the risk that Keybridge might not readily recover the transferred funds if it succeeded on appeal. It was material to order 3, not a conclusion about every payment required by the Supreme Court orders.
At [60], the Court says material prejudice would be caused to Keybridge if order 3 were not stayed. The accompanying reasoning matters: the Court was also not satisfied that a stay of that order would materially affect Mr Bolton’s ability to obtain representation. The outcome turned on the comparison between those particular risks.
At [61], Stern JA identifies the opposing concern for order 5. A stay would create a significant risk of prejudice to Mr Bolton’s ability to obtain representation for the NSW trial beginning on 23 June. The appeal hearing was scheduled for 18 June, leaving only five days before that trial. The timing made the potential effect of withholding later payments materially different from the effect of staying the immediate transfer.
At [62], the Court explains why order 7 remained in place: it required ordinary-basis costs to be agreed or assessed, and there was no evidence that payment would precede the appeal’s determination. The Court therefore did not treat a possible future costs obligation as sufficient, on its own, to justify a stay.
The judgment is most relevant to stay applications where a party appeals an order requiring money to be paid before the appeal is decided, and the evidence raises a concrete concern that repayment could be delayed or difficult if the appellant succeeds. Here, the Court relied on the substantial sums in order 3, Mr Bolton’s lack of currently available funds, and uncertainty about when those funds might become available ([58]–[60]).
It is also instructive where an appeal is expedited but another hearing is imminent. The five-day gap between the appeal hearing and the NSW trial was central to the Court’s assessment of order 5. The judgment shows why a court may distinguish between a payment required immediately and payments that may be needed to secure representation for a near-term trial ([61]).
The decision is also relevant where a judgment contains several payment-related orders with different purposes and timing. Stern JA assessed each separately: an immediate transfer, payments of future costs within specified periods, and ordinary-basis costs to be agreed or assessed ([12], [57]–[63]). The decision does not state that these facts automatically determine a stay application. Its method is a contextual comparison of evidenced prejudice.
A further feature is the need to examine the evidence supporting each party’s asserted prejudice. For example, the Court attached little weight to Mr Bolton’s assertion about the value of Australian assets because no documentary evidence was provided, and it rejected an inference of Keybridge’s solvency risk in the absence of direct evidence ([21], [52]). Those findings illustrate the evidentiary focus of this motion; they are not findings that either party’s broader financial position was finally determined.
The supplied judgment contains no decisions of later courts applying or distinguishing Keybridge Capital Ltd v Bolton. Its decision date is 11 June 2026, and the text records that the appeal was listed for 18 June 2026, but it provides no outcome of that appeal or subsequent treatment ([6]). It would therefore be unsupported to say how later courts have treated this judgment.
Within this judgment, Stern JA applied existing stay principles and discussed earlier authorities. The Court relied on the stay framework set out in Michael Hill Jeweller, and referred to Black Label Developments Pty Ltd v McMenemy and New South Wales Bar Association v Stevens for the statutory and interests-of-justice principles ([39]–[40]). It considered Port Macquarie-Hastings Council and Woolworths relevant to the risk that money may not be repaid readily if an appeal succeeds ([42]–[43]).
The Court also referred to National Roads and Motorists’ Association v Whitlam in summarising Keybridge’s submission about costs incurred “as an officer” ([47]). The judgment does not decide that issue as a separate question on the stay motion. The central ruling was confined to whether particular orders should operate while the appeal was pending.
The appeal’s ultimate construction questions remained unresolved in this decision. Stern JA found only that the appeal raised a serious issue, referring to the proper construction and ambit of clauses 3.1, 3.3 and 3.4 of the Director’s Deed ([56]). The judgment does not determine whether the deed required the payments in dispute or how the appeal grounds concerning s 199A of the Corporations Act should ultimately be resolved.
The judgment also does not determine whether Mr Bolton was ultimately entitled to indemnification for the costs covered by the Supreme Court orders. The declaration itself preserved Keybridge’s right to recover payments if it was later established that Mr Bolton was not entitled to indemnity, reflecting the statutory restriction described at [9].
The reasons do not reveal the final outcome of the appeal or whether the stay was later varied. The order stayed order 3 pending final determination of the appeal or further order, and granted liberty to apply on one business day’s notice ([6]). The supplied text gives no later procedural history.
Finally, the judgment does not decide the parties’ broader disputes concerning the NSW or Italian proceedings, the freezing orders, Mr Bolton’s asserted employment entitlements, or the merits of the underlying claims about the payment to Crotto del Nino S.r.l. Those matters appear as context for the stay motion, rather than issues resolved by Stern JA ([22]–[28]).
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Source: NSW Caselaw (www.caselaw.nsw.gov.au). Converted to plain text by ZoeLaw. Not the official version.
Medium Neutral Citation: Keybridge Capital Ltd v Bolton [2026] NSWCA 109
Hearing dates: 9 June 2026
Date of orders: 9; 11 June 2026
Decision date: 11 June 2026
Before: Stern JA
Decision: (1) Upon Keybridge Capital Limited giving the usual undertaking as to damages, order 3 of the Orders made by Nixon J in Supreme Court of NSW proceeding no 2026/00163283 on 29 May 2026 is stayed pending the final determination of the appeal brought by Keybridge Capital Limited against the decisions of Nixon J in Bolton v Keybridge Capital Limited [2026] NSWSC 562 and Bolton v Keybridge Capital Limited (No 2) [2026] NSWSC 604 or until further order.
(2) Set down the appeal for hearing on 18 June 2026 with a time estimate of half a day.
(3) The appellant to file and serve written submissions by 4 pm on 11 June 2026.
(4) The respondent to file and serve written submissions by 4 pm on 15 June 2026.
(5) The appellant to file and serve submissions in reply by 4 pm on 16 June 2026.
(6) Direct the Registrar to make other directions as to the preparation of appeal books and otherwise readying the matter for hearing.
(7) Liberty to apply on one business day’s notice to Justice Stern by her Associate, or the Registrar.
(8) Costs of the motion be costs in the appeal.
(9) The motion be otherwise dismissed.
Catchwords: PROCEDURE — application for stay of orders pending appeal — where expedition of appeal ordered — where freezing orders in place — where balance of convenience favoured stay of order
Legislation Cited: Civil Procedure Act 2005 (NSW), ss 56, 135
Corporations Act 2001 (Cth), ss 199A, 237
Cases Cited: Black Label Developments Pty Ltd v McMenemy [2025] NSWCA 114
Bolton v Keybridge Capital Limited [2026] NSWSC 562
Bolton v Keybridge Capital Limited (No 2) [2026] NSWSC 604
Bolton v WAM Active Ltd [2025] NSWCA 81
In the matter of Keybridge Capital Limited [2024] NSWSC 1215
In the matter of Keybridge Capital Limited [2025] NSWSC 240
In the matter of Keybridge Capital Limited (No 2) [2025] NSWSC 354
Michael Hill Jeweller (Australia) Pty Ltd v Gispac Pty Ltd [2024] NSWCA 128
National Roads and Motorists’ Association v Whitlam [2007] NSWCA 81
New South Wales Bar Association v Stevens [2003] NSWCA 95
Port Macquarie-Hastings Council v Diveva Pty Limited ABN 34 003 779 815 trading as Mid Coast Road Services [2017] NSWCA 4
WAM Active Limited v Keybridge Capital Limited (No 2) [2024] NSWSC 1496
Woolworths Ltd v Strong (No 2) (2011) 80 NSWLR 445
Category: Principal judgment
Parties: Keybridge Capital Limited (Applicant on motion / Appellant)
Nicholas Francis John Bolton (Respondent on motion / Respondent)
Representation: Counsel:
PM Wood and D Krochmalik (Applicant on motion / Appellant)
V Murano (Respondent on motion / Respondent)
Solicitors:
Gadens (Applicant on motion / Appellant)
File Number(s): 2026/223425
Publication restriction: Nil
By notice of motion filed 1 June 2026 the applicant, Keybridge Capital Limited, sought a stay of orders 3, 5 and 7 of orders of Nixon J on 29 May 2026: Bolton v Keybridge Capital Limited (No 2) [2026] NSWSC 604 (Bolton (No 2)). The stay was sought until the final determination of Keybridge’s appeal, filed on 30 May 2026, against Bolton (No 2) and the earlier decision of Nixon J in Bolton v Keybridge Capital Limited [2026] NSWSC 562 (Bolton (No 1)). In Bolton (No 1) Nixon J set out his Honour’s substantive conclusions on the issues raised in those proceedings, and in Bolton (No 2) his Honour determined what orders should be made to reflect those substantive conclusions.
Keybridge also sought an order expediting the appeal.
Keybridge offered the usual undertaking as to damages if a stay were granted.
On 3 June 2026 the Court of Appeal Registrar stayed orders 3, 5 and 7 until 4 pm on 9 June 2026.
The respondent, Nicholas Bolton, who appeared at the hearing of the motion by Counsel, opposed the grant of a stay.
At the conclusion of the hearing of Keybridge’s motion on 9 June 2026 I made the following orders:
Upon Keybridge Capital Limited giving the usual undertaking as to damages, order 3 of the Orders made by Nixon J in Supreme Court of NSW proceeding no 2026/00163283 on 29 May 2026 is stayed pending the final determination of the appeal brought by Keybridge Capital Limited against the decisions of Nixon J in Bolton v Keybridge Capital Limited [2026] NSWSC 562 and Bolton v Keybridge Capital Limited (No 2) [2026] NSWSC 604 or until further order.
Set down the appeal for hearing on 18 June 2026 with a time estimate of half a day.
The appellant to file and serve written submissions by 4 pm on 11 June 2026.
The respondent to file and serve written submissions by 4 pm on 15 June 2026.
The appellant to file and serve submissions in reply by 4 pm on 16 June 2026.
Direct the Registrar to make other directions as to the preparation of appeal books and otherwise readying the matter for hearing.
Liberty to apply on one business day’s notice to Justice Stern by her Associate, or the Registrar.
Costs of the motion be costs in the appeal.
In Bolton (No 2) Nixon J declared, in order 1, that cl 3.1 of a Director’s Deed dated 2 January 2013, entered into by Keybridge and Mr Bolton, required Keybridge to pay Mr Bolton’s costs of defending proceedings 2024/00065373 in the Supreme Court of New South Wales (NSW p****roceedings) and Court of Milan proceedings RGAC 45476/2025 and RG 351/2026 and the proceeding initiated by a Deed of Foreclosure filed in the Tribunal of Como and dated 17 April 2026 (Italian p****roceedings) as and when those costs are incurred, on the basis that Keybridge has a right to recover those payments from Mr Bolton in the event, and to the extent, that it is subsequently established that Mr Bolton is not entitled to indemnity in respect of such amounts.
The latter condition gives effect to the terms of s 199A(3) of the Corporations Act 2001 (Cth), which provides that:
A company or related body corporate must not indemnify a person (whether by agreement or by making a payment and whether directly or through an interposed entity) against legal costs incurred in defending an action for a liability incurred as an officer or auditor of the company if the costs are incurred:
(a) in defending or resisting proceedings in which the person is found to have a liability for which they could not be indemnified under subsection (2) [relevantly, a liability owed to the company]
…
As is clear, Nixon J did not make any declaration that Keybridge was obliged under cl 3.1 of the Director’s Deed to indemnify Mr Bolton in respect of his legal costs of the proceedings before his Honour. Rather, as set out at [12] below, his Honour simply ordered that Keybridge should pay the costs of the proceedings.
In its grounds of appeal in the appeal, Keybridge contended that Nixon J erred in concluding that cl 3.1 of the Director’s Deed obliged Keybridge to indemnify Mr Bolton for costs incurred by him in defending a claim of a type to which ss 199A(2)-(3) of the Corporations Act 2001 (Cth) is directed and/or in concluding that cl 3.1 applied to liabilities incurred by Mr Bolton as an officer of Keybridge based on his conduct at any time during which he was an officer of Keybridge.
The application for a stay was brought, as set out above, pending the outcome of the appeal. Keybridge did not seek to stay order 1. Its application was to stay only orders 3, 5 and 7, which are in the following terms:
(3) Order that, pursuant to the declaration in order (1) above, [Keybridge] transfer $210,839.38 and €80,026.96 to the Speed and Stracey Lawyers Pty Limited Statutory Trust Account by 3 June 2026.
…
(5) Order that amounts to be paid to [Mr Bolton] pursuant to the declaration in order (1) above are to be paid by [Keybridge]:
(a) within three business days to the extent the hearing dates for the [NSW proceedings] remain 23-26 June 2026;
(b) within three business days to the extent the invoices are provided to [Keybridge] at a time that is within one month of alternative final hearing dates for the [NSW proceedings]; and
(c) otherwise, within seven business days.
…
(7) Order that [Keybridge] pay [Mr Bolton’s] costs of this proceeding on the ordinary basis, as agreed or assessed.
3.1 Indemnity
The Company must indemnify the Director, on a full indemnity basis and to the full extent permitted by law, against all losses, liabilities incurred by the Director as an officer of the Company or a related body corporate.
3.2 Continuing indemnity
The indemnity in clause 3.1 is an irrevocable, unconditional, continuing and principal obligation of the Company despite:
(a) the resignation or removal of the Director as a director of the Company;
(b) the settlement of any dispute between the Director and the Company or a third party; or
(c) the occurrence of any other thing,
and remains in full force and effect until released by the Director.
3.3 Advance of defence costs
(a) The Company, on the Director's request, will advance to the Director reasonable costs incurred or expected to be incurred by the Director (whether legal or otherwise) in defending Relevant Proceedings. Any such advance will be interest free.
(b) The Director must furnish the Company with invoices or other relevant evidence of the costs incurred under clause 3.3(a).
(c) If the Company has advanced an amount for costs under clause 3.3(a), the amount of the advance will be in part satisfaction of the Company's obligation to indemnify the Director and will cease to be repayable unless it is subsequently found that the Director was not entitled to be indemnified for those costs.
(d) If the Company has paid an amount under clause 3.1 or advanced an amount for costs under clause 3.3(a) and it is subsequently found that the Director was not entitled to be indemnified for or advanced those costs, or where the amount advanced by the Company is in excess of the costs for which the Director is entitled to be indemnified, the Director must repay the amount of the payment, advance or part thereof (as applicable) to the Company within 90 days of a request by the Company.
Clause 3.4(a) provides that the company may assume the conduct, negotiation or defence of a claim and if it does so, the conduct of the claim will be under the sole management and control of the company or its insurers (acting reasonably).
Relevant Proceedings are defined in cl 1.1 of the Director’s Deed as:
in relation to a director:
1 any hearing, conference, dispute, inquiry or investigation of a court, arbitrator, mediator, tribunal or governmental or administrative body; and
2 any procedural step preceding or otherwise relating to such a hearing, conference, dispute, inquiry or investigation,
in which the director is involved:
3 as a party, witness or otherwise; and
4 because the director is or was a director of the Company (or a related body corporate) in the Relevant Period.
Relevant Period is defined as “the period commencing on the Appointment Date and ending on the date the Director ceases to act as a director of the Company or a related body corporate (as applicable)”.
Nixon J found, relevantly, that having regard to the definition of Relevant Period, the NSW proceedings were not Relevant Proceedings as defined in the Director’s Deed. There was thus no obligation under clause 3.3(a) of the Director’s Deed for Keybridge to advance costs incurred or expected to be incurred by Mr Bolton in respect of the NSW proceedings. Rather, as is clear from the terms of order 1, his Honour found that the relevant obligation on Keybridge arose under cl 3.1 of the Director’s Deed.
Keybridge is a public company whose shares are listed on the Australian Securities Exchange but trading in its shares has been suspended since before February 2025, and Keybridge was under administration from 9 February 2025 until 8 May 2025. Mr Bolton was a director of Keybridge over three periods:
between 30 December 2011 and 9 October 2012;
between 2 January 2013 and either 17 November or 17 December 2015; and
between 13 October 2019 until 10 February 2025.
In 2016, following Mr Bolton’s disqualification as a director, Keybridge agreed to advance a loan to Mr Bolton to fund legal costs incurred in challenging the disqualification decision. Keybridge advanced funds to Mr Bolton pursuant to this agreement. The terms of that loan included a requirement upon Mr Bolton to repay 50% of the sums lent and to direct any costs paid to repayment of the advance. One of the matters that Keybridge relies upon in support of the motion before this Court was that Mr Bolton has not repaid the sums loaned pursuant to this agreement (albeit there is no evidence of any request being made to Mr Bolton to make repayment under the loan agreement).
Since 2024 litigation has been on foot between Keybridge, Mr Bolton, WAM Active Limited and others.
In the motion before this Court, Mr Bolton relied upon evidence that the most recent financial statements that Keybridge had lodged with ASIC related to the half year ending 31 December 2024, which was before it went into administration. Mr Bolton submitted that I should draw the inference from this that Keybridge’s solvency was at risk. I would not draw that inference. Nor would I draw that inference from the fact that Nixon J’s conclusion in April 2025 that Keybridge was solvent, in In the matter of Keybridge Capital Limited (No 2) [2025] NSWSC 354 at [215], was reached including by reference to evidence that a facility agreement provided to Keybridge by WAM Active had no carve-out for funds advanced to indemnify directors’ legal costs which evidence now adduced by Mr Bolton indicates was not the case. Indeed, in the absence of any direct evidence suggesting that Keybridge currently has solvency issues I would not infer that there is any risk that a short stay would have any impact upon the likelihood that Keybridge will be able to transfer funds as required under the orders of Nixon J. I thus reject Mr Bolton’s contention that there is a risk that sums may not be paid under the orders of Nixon J if I grant a stay. In any event, as Keybridge contended, given the short period of any stay this contention lacked merit.
The proceedings heard by Nixon J in May 2026 involved a claim by Mr Bolton for an indemnity, including under cl 3.1 and/or cl 3.3(a) of the Director’s Deed, in respect of his costs of defending the claim against him brought by Keybridge in the NSW and the Italian proceedings. For the purposes of this motion it is unnecessary to delve into the detail of the NSW proceedings. It suffices to observe that on 27 November 2024, Nixon J granted leave to WAM Active, the largest shareholder in Keybridge, to bring a derivative action under s 237 of the in the name of Keybridge against Mr Bolton and his then-fellow directors: [2024] NSWSC 1496 at [241]. The claim concerned a payment by Keybridge of $4.75 million to an Italian company associated with Mr Bolton, del Nino S.r.l.. The payment was made for the benefit of Mr Bolton, so as to allow him to acquire shares in Crotto which, in turn, acquired a property in Lake Como: at [240]. In the NSW proceedings Keybridge contends that Mr Bolton breached his duty as a director of Keybridge, including in respect of the payment of $4.75 million.
[t]he firm is now facing proceedings brought by Yowie impugning some $660,000-odd received across your various matters [redacted]. There is a risk of a perception of a conflict of interest arising in the firm defending these proceedings fully whilst simultaneously advancing your interests in other proceedings.
I infer that this letter set out the reason why Hamilton Locke came off the record in the NSW proceedings, namely on account of a risk of a perceived conflict of interest, noting that Mr Bolton is a former managing director and Chief Executive Officer of Yowie Group Limited. In these circumstances, and in light of the fact that there was no evidence before me that suggested that Hamilton Locke would act for Mr Bolton in the NSW proceedings if it were paid moneys which Mr Bolton owed to it, I am not satisfied that the grant of a stay of order 3 would have any impact upon the prospect that Hamilton Locke might agree to represent Mr Bolton in the NSW proceedings. In this regard I reject Mr Bolton’s submission, which was not in any event supported by any evidence, that if the fees of Hamilton Locke (that are the subject of order 3) were paid, “Hamilton Locke will likely be in a position to recommence acting for Mr Bolton”.
On 9 March 2026, the NSW proceedings were listed for a final hearing before Brereton J on 23 June 2026 with a time estimate of four days. The parties to those proceedings are WAM Active, Keybridge, Mr Bolton, Crotto and two others.
In March 2026 Mr Bolton wrote on a number of occasions seeking that Keybridge make payment under the indemnity in the Director’s Deed for costs incurred in both the Italian and the NSW proceedings. Keybridge refused to do so.
By summons filed on 21 April 2026 Mr Bolton commenced the proceedings heard by Nixon J in May 2026. In support of his claim before Nixon J, Mr Bolton relied upon the following passage from his affidavit:
In the present circumstances, I do not have the cash or ability to obtain cash in order to fund the defence of the [NSW proceedings] unless Keybridge, in accordance with the Directors’ Deed …. advances funds and, or alternatively, agreed to pay my costs, to enable me to obtain adequate representation to defend the [NSW proceedings].
If this proceeding … is not determined well prior to the time necessary to prepare for the [NSW proceedings], I am concerned that I will not be able to obtain representation in the [NSW proceedings] and this will prejudice my defence of the [NSW proceedings].
The proceedings were heard by Nixon J on 18 May 2026. His Honour delivered reasons for judgment on 21 May 2026: Bolton (No 1). Final orders were made in Bolton (No 2) on 29 May 2026, following a further hearing**.** I infer that Nixon J heard and determined those proceedings with great expedition, and framed orders 3 and 5 in the way he did, to ensure that his orders would enable Mr Bolton (if he chose and if that representation was available to him) to take advantage of the indemnity in cl 3.1 of the Director’s Deed (as his Honour construed it) to fund representation for the hearing before Brereton J commencing on 23 June 2026.
Mr Bolton also relied upon an email of 1 June 2026 to him from Malcolm Stewart, his solicitor in the proceedings before Nixon J. This email was in response to an earlier email from Mr Bolton asking that Mr Stewart’s firm (Speed and Stracey Lawyers) act for him on the motion before this Court. Mr Stewart wrote:
1. There is no basis upon which this firm has to, or is any way required to act for you in the Appeal.
2. I made it plain to you on Friday, and in subsequent communications that unless and until counsel’s fees and our fees for the Indemnity Proceedings and the Appeal were paid or otherwise agreed upon, we could not act for you on the Appeal or in the [NSW proceedings]. That remains the position.
3. The orders made in your proceedings are for your benefit, not this firm’s.
4. If you would like to discuss how you can ensure all the payments for the existing outstanding invoices can be paid and fees for the Appeal can be secured by payment into our trust account, I am prepared to discuss our possible representation with you.
5. We enclose the other invoices for the last part of the indemnity Proceedings.
It is not clear what, if any, response was given by Mr Bolton to this email. Mr Murano of Counsel represented Mr Bolton at the hearing of the motion seeking a stay (albeit without solicitors). Moreover, when I was seeking available dates for the hearing of the appeal, Mr Murano indicated that he had available dates from Senior Counsel (presumably) briefed on the appeal. The appeal was fixed later than would otherwise have been the case to accommodate those dates.
I do not infer from Mr Stewart’s email that the stay of the orders of Nixon J would prevent Mr Bolton obtaining representation for the appeal. It is apparent that Mr Bolton has obtained at least counsel to represent him on the stay application and on the appeal. Further, Nixon J did not find that the Director’s Deed encompassed the costs of the proceedings before his Honour (and it would follow of the appeal) and those proceedings are not covered by the declaration in order 1 (to which order 5 relates). Nixon J ordered that those costs be paid on the ordinary basis as agreed or assessed, not that they be indemnified under the Director’s Deed. The fact that Mr Bolton has served of a letter of demand on Keybridge to indemnify his costs of the proceedings before Nixon J under the Director’s Deed, does not take matters further. The fact remains that there is no finding that the costs of the proceedings before Nixon J, nor it would follow of the appeal, fall within the ambit of the Director’s Deed. In these circumstances, I am not satisfied that a stay of the orders of Nixon J would have any material impact upon Mr Bolton’s ability to obtain representation for the appeal.
By way of context, I also observe that, before Nixon J, Mr Stoljar SC, who represented Mr Bolton before Nixon J, addressed the issue of the costs of those proceedings and the order he sought was that party/party costs be paid on the usual basis.
Keybridge sought a stay of the orders of Nixon J pursuant to s 135 of the Civil Procedure Act 2005 (NSW) or the Court’s inherent jurisdiction. There is no dispute that the power in s 135 extends to the grant of a stay. The power under s 135 is subject to other provisions of the Civil Procedure Act, including s 56, and must be exercised judicially: Black Label Developments Pty Ltd v McMenemy [2025] NSWCA 114 at [47]. The overriding principle is the interests of justice: New South Wales Bar Association v Stevens [2003] NSWCA 95 at [83].
Payne JA explained in Michael Hill Jeweller (Australia) Pty Ltd v Gispac Pty Ltd [2024] NSWCA 128 at [5] that:
The principles governing the grant of a stay pending an appeal are well-settled, as the parties on this application agreed. They are analogous to those which govern the grant of interlocutory relief before trial: Alexander v Cambridge Credit Corp Ltd (1985) 2 NSWLR 685 at 694-5, Kalifair Pty Ltd v Digi-Tech (Australia) Ltd (2002) 55 NSWLR 737; [2002] NSWCA 383 at [18]. A party applying for a stay must show, first, that the appeal raises serious issues for determination by the appellate court; and secondly, that there is a real risk that the appellant will suffer prejudice or damage if the stay is not granted. If an appellant prevails on those two questions, then the Court is to consider the balance of convenience and the competing rights of the parties: Pamplin v Irwin [2024] NSWCA 112 at [11] per Leeming JA.
… there is no dispute that in an application of this kind the Court does not, generally speaking, speculate as to the strength or otherwise of the prospects of success, although it may make some preliminary assessment so as to exclude an appeal which has been lodged without any real prospect of success so as to gain time: see Kalifair Pty Ltd v Digi-Tech (Australia) Ltd (2002) 55 NSWLR 737; [2002] NSWCA 383 at [18]-[19]; Qasim v PF 473 Pty Ltd [2024] NSWCA 248 at [10]. …
The risk that a judgment may not be able to be repaid may be taken into account when considering whether to grant a stay: Port Macquarie-Hastings Council v Diveva Pty Limited ABN 34 003 779 815 trading as Mid Coast Road Services [2017] NSWCA 4 at [36]. Keybridge relied also upon the observation of Campbell JA (Handley AJA and Harrison J agreeing) in Woolworths Ltd v Strong (No 2) (2011) 80 NSWLR 445 at [68] referring to the “usual practice of staying judgments pending appeal where there is a risk that the plaintiff will be unable to repay the money without difficulty or delay if the appeal were to succeed” and reiterating the importance of that practice.
Mr Bolton submitted that both Port Macquarie-Hastings Council and Woolworths are “entirely different” to the present case given that Mr Bolton was not awarded damages or restitution. I am satisfied that both Port Macquarie-Hastings Council and Woolworths are relevant to the motion now before the Court. They indicate that the courts have recognised as important that a stay might be granted where there is a risk that monies which the relevant orders require be paid might ultimately either not be repaid (if the orders are set aside or varied) or might only be repaid with difficulty or delay. That is, of course, not to say that this is a determinative factor. Rather, the cases recognise that this may be material prejudice to be considered when determining what the interests of justice require.
Keybridge contended that its appeal grounds are, at least, reasonably arguable and that it would suffer likely irremediable prejudice if a stay was not granted. They made the following submissions as to prejudice (I do not here repeat matters I have already dealt with).
First, Keybridge submitted that the likelihood is that, if it succeeds on appeal, there will be meaningful delay in it being repaid any amounts which it will have transferred pursuant to orders 3, 5 and 7, or that those sums would never be repaid. In this regard they rely upon the following:
Mr Bolton deposed in his affidavit that he does not have the cash and does not have the ability to obtain cash to pay legal fees;
Mr Bolton did not repay sums owing pursuant to the loan agreement at [19] above (I attach no weight to this in circumstances where no request was made for repayment);
Crotto’s bankers wrote to Crotto on 12 May 2026 indicating that Crotto had failed to make at least one repayment (noting that the terms of the translation of the letter in evidence are ambiguous as to whether it is only one payment, or all payments, that have not been made) under a mortgage loan agreement. Keybridge contended that the action taken by the bank supports its contention that Mr Bolton does not have money or assets available to meet any obligation to repay Keybridge if Keybridge succeeds on appeal and that this was so even if the letter identified only that Keybridge had failed to make one required payment under the loan; and
any repayment that might be required from Mr Bolton if Keybridge is successful on appeal will be delayed for an uncertain period by reason of the freezing orders (and orders of that nature) in the NSW and Italian proceedings.
Second, Keybridge submitted that any comparative prejudice to Mr Bolton is slight as:
the sums which are the subject of the orders have been owing for some time and there is no suggestion that his former legal representatives have taken any step to recover their fees outstanding. Moreover, the evidence suggests that Hamilton Locke ceased acting for Mr Bolton by reason of a perceived conflict of interest and thus would not represent Mr Bolton in the NSW proceedings even if no stay was granted (see above at [29]-[30] above). Keybridge contends that there is no evidence that Mr Bolton’s ability to secure representation in the NSW proceedings turns on whether or not a stay is granted. In any event, Keybridge said, Mr Bolton could apply to vacate the hearing listed to commence on 23 June 2026 and, in any event, Mr Bolton remains unrepresented in the NSW proceedings and there is no reason to think that any amounts will be payable under order 5; and
Mr Bolton waited until late April 2026, after the NSW proceedings were listed for a four day hearing commencing on 23 June 2026, to bring the claim for indemnification of legal costs under the Director’s Deed in circumstances where there is no reason why this issue could not have been litigated earlier.
The balance of convenience favours the grant of a stay of order 3 pending final determination of the appeal or further order in circumstances in which, at the commencement of the hearing, I listed the appeal for hearing on 18 June 2026.
The amounts to be paid under order 3 are not insubstantial. Some of those sums would, under his Honour’s orders, be paid out to solicitors in Italy. Some would be transferred to Hamilton Locke.
Any order for repayment of sums transferred pursuant to order 3 would have to be made against Mr Bolton as the party to the proceedings. Whilst I accept that the terms of the letter to Crotto at [45] above are ambiguous, it is clear that Mr Bolton does not have monies currently available to him to repay sums paid pursuant to the orders of Nixon J. Further, it is uncertain when (and potentially if) that money might become available to Mr Bolton.
In these circumstances, I am satisfied that material prejudice would be caused to Keybridge if there was no stay of order 3. In circumstances where the evidence before me does not satisfy me that a stay of order 3 would have any material impact upon Mr Bolton’s ability to obtain representation for either the NSW proceedings or the appeal (having regard to my findings at [30] and [37] above), the balance of convenience clearly favours the grant of a stay of order 3.
As regards order 5, the position is different. I readily infer that a stay of order 5 would give rise to a significant risk of prejudice to Mr Bolton’s ability to obtain legal representation for the hearing listed to commence on 23 June 2026 before Brereton J. The hearing of Keybridge’s appeal will take place on 18 June 2026, only five days before those proceedings will commence. In circumstances where the hearing before Brereton J was listed in March 2026, and there are multiple parties to those proceedings, I did not regard Keybridge’s contention that Mr Bolton could apply for that hearing to be vacated as offering any appropriate response to this prejudice. I am also satisfied that the extent of the prejudice to Keybridge by reason of order 5 is minimised (but not eliminated) by the fact that I anticipate that Keybridge’s appeal will be finally determined on or shortly after 18 June 2026, and order 5 requires payment within three business days of costs being incurred. Both of those factors will limit the extent of the prejudice occasioned to Keybridge by order 5, pending final determination of the appeal. Mr Bolton’s delay in bringing the proceedings before Nixon J does not suffice to overcome significant risk of prejudice to Mr Bolton.
Given my analysis of order 7, no prejudice will be occasioned to Keybridge if no stay of order 7 is ordered. Order 7 requires no more than that costs of the proceedings before Nixon J be paid on the ordinary basis as agreed or assessed. There is nothing before me to suggest that that assessment or agreement will precede final determination of the appeal, or that the terms of any agreement would require that costs be paid prior to the final determination of the appeal.
**********
Keybridge Capital Ltd
Bolton
[2026] NSWSC 562
[2026] NSWSC 604
(2011) 80 NSWLR 445
(1985) 2 NSWLR 685
(2002) 55 NSWLR 737
Order 3 of Nixon J’s orders was stayed pending final determination of the appeal or further order, conditional on Keybridge giving the usual undertaking as to damages. The appeal was expedited and listed for 18 June 2026. Stays of orders 5 and 7 were refused. The motion was otherwise dismissed, and its costs were made costs in the appeal.
These are my reasons for making those orders. In addition, I order that the motion filed by Keybridge on 1 June 2026 is otherwise dismissed. That order is implicit in the orders I made on 9 June 2026 but should be added for the avoidance of doubt.
On 20 September 2024 f****reezing orders were made by Black J in the NSW proceedings: In the matter of Keybridge Capital Limited [2024] NSWSC 1215. These orders froze Mr Bolton’s assets up to the unencumbered value of $4,750,000. The freezing orders have been extended on a number of occasions and by an order of 23 June 2025, they were extended “until further order”. They provide that Mr Bolton could remove from Australia, dispose or deal with assets so long as the unencumbered value of his Australian assets exceeds the amount of $4,750,000. Mr Bolton says in his affidavit affirmed on 1 May 2026 that, notwithstanding that (he says) his assets in Australia have a total unencumbered value exceeding this amount, he has been unable to access any of his Australian bank accounts or to obtain funding or otherwise refinance existing liabilities to fund his defence of the NSW proceedings.
On 10 February 2025 Mr Bolton was removed as a director of Keybridge at a meeting of its members. On 21 March 2025 Nixon J declared that that meeting was validly held and that Mr Bolton was removed as director at that meeting: In the matter of Keybridge Capital Limited [2025] NSWSC 240. He relies upon this in support of his contentions that the grant of the stay sought by Keybridge would cause him prejudice, as he asserts that Keybridge’s failure to pay what he describes as his “contractual and statutory entitlements” means that he does not have money which he otherwise would have had to fund the NSW proceedings.
On 26 June 2025, through his then-solicitors Hamilton Locke, Mr Bolton requested that Keybridge pay his incurred and future costs of the NSW proceedings. On 22 July 2025, Keybridge refused.
Mr Bolton commenced proceedings in the Federal Circuit and Family Court of Australia on 15 December 2025, seeking to recover what he contends is $1.855 million in unpaid salary and entitlements plus statutory penalties.
On 22 December 2025, Mr Bolton requested that Keybridge indemnify him in respect of his legal costs incurred in the Italian proceedings. Keybridge rejected this request on 8 January 2026.
As already noted, WAM Active and Keybridge also commenced the Italian proceedings in which they seek precautionary seizure orders against Mr Bolton and Crotto by reference to the prospective judgment in the NSW proceedings. On 3 March 2026 the Court of Milan granted orders in the nature of freezing orders over Mr Bolton’s Italian assets. Mr Bolton says in his affidavit that these orders preclude him from obtaining sufficient funds to defend the NSW proceedings by using his Italian assets.
On 6 March 2026, Hamilton Locke, Mr Bolton’s former solicitors in the NSW proceedings, came off the record in those proceedings. Shortly after this, on 21 April 2026, Brit Ibanez, Managing Partner of Hamilton Locke explained to Mr Bolton that:
Third, as regards order 7, Keybridge submitted that Mr Bolton could not now contend, when seeking to resist the stay sought by Keybridge, that those costs fall within the ambit of the Director’s Deed or that Keybridge is required to pay them on an indemnity basis in circumstances where that contention was not made before Nixon J. Keybridge relied also upon N**ational R**oads and M**otorists’ A**ssociation v Whitlam [2007] NSWCA 81 at [78]-[80] where, for the purposes of an indemnity for costs incurred by an officer of a corporation “as an officer”, a distinction is drawn between costs incurred by reason of actions as an officer and costs incurred in defamation proceedings arising out of an allegation made as to how the officer had performed his or her duties as an officer. Keybridge contended that, having regard to that distinction, Mr Bolton’s costs of the proceedings before Nixon J did not fall within the ambit of the Director’s Deed.
For his part, Mr Bolton contended that the prospects of the appeal are weak, and relied upon this as weighing heavily against the grant of the stay sought.
Mr Bolton contended that the grant of a stay would deprive him of the ability to obtain and fund legal representation in both the NSW proceedings and the Italian proceedings, which was the very purpose for the orders of Nixon J. He contended that Keybridge should not, by a stay, be able to frustrate the contractual rights Nixon J recognised as subsisting.
Mr Bolton also contended that, if a stay of order 5 were granted, he would suffer immediate and substantial prejudice as “he cannot otherwise meet those costs of the [NSW] Proceeding[s]”. He contended, in effect, that he wished to rely upon the orders of Nixon J for the purpose of requiring Keybridge to pay funds to him so that he could pay for legal representation in the NSW proceedings. I have already rejected Mr Bolton’s related contention that the stay would preclude Hamilton Locke from being retained by him in the NSW proceedings.
As set out above, Mr Bolton also asserted that his ability to fund the NSW proceedings and the appeal had been impacted by the breaches that he was litigating in the Federal Circuit and Family Court proceedings (above at [26]).
Mr Bolton contended, further, that he has assets that will enable him to repay funds if Keybridge succeeds in its appeal. In this regard, he relied upon the fact that, he asserted, he has assets worth $4.75 million in New South Wales which are subject to the freezing orders, and assets worth $4.7 million in Italy. As to the former, Mr Bolton relied upon his assertion, in his affidavit, that he has assets with a total unencumbered value greater than $4.75 million which are currently beyond his reach by reason of the freezing orders. There is no evidence of this, however, beyond the mere fact of Mr Bolton’s assertion, albeit that it would plainly have been within Mr Bolton’s power to adduce documentary evidence as to the value of his Australian assets. In these circumstances, I attach little weight to Mr Bolton’s assertion. In any event, on Mr Bolton’s evidence he is not able to access these assets to pay legal costs and, I would infer, he would similarly be unable to access these to repay sums paid under the orders of Nixon J.
As to the asserted value of his assets in Italy, Mr Bolton relied upon an extract from a judgment of the Court of Milan, quoted by Nixon J in Bolton (No 1)**, identifying that the “credit to be protected, which is the subject of the compensatory suit, amount[ing] to 4.7[m] Australian dollars”. It is not clear whether Nixon J is here referring to the amount claimed in the NSW proceeding or to the value of Mr Bolton’s assets secured by the Court of Milan’s order. In any event, given that these are assets in Italy which are subject to orders in the nature of a freezing order, nothing turns on how Nixon J’s words should be construed.
Mr Bolton also contended that the prejudice Keybridge relies upon is overstated.
In the circumstances I am not satisfied that the balance of convenience favours the grant of a stay of either order 5 or order 7.