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PUIL - Special Economic Measures Act (SEMA). Fridman v. Canada (Foreign Affairs)
In Fridman v. Canada (Foreign Affairs) (Fed CA, 2026) the Federal Court of Appeal dismissed an appeal, this brought against an earlier dismissal of a JR, that brought against the Minister of Foreign Affairs' refusal to remove the appellant's names from a SEMA sanctions list.
Here the court illustrates the sanction aspects of SEMA law, all of which is little-litigated:[1] After Russia commenced hostilities against Ukraine, the Governor in Council formed "“the opinion that the actions of the Russian Federation constitute a grave breach of international peace and security that has resulted or is likely to result in a serious international crisis”": Special Economic Measures (Russia) Regulations, SOR/2014-58, preamble [Russia Regulations]. This led the Governor in Council to make the Russia Regulations restricting and prohibiting persons in Canada and Canadians outside Canada from engaging in certain activities: Special Economic Measures Act, S.C. 1992, c. 17, s. 4.
[2] The Russia Regulations permit the Governor in Council to add a person to a sanctions list if the Governor in Council, on the recommendation of the Minister of Foreign Affairs, is satisfied that there are reasonable grounds to believe the person is one described in one of the paragraphs in section 2 of those regulations. Paragraph 2(d) refers to a family member of an associate referred to in paragraph 2(c). Once a person is added to the sanctions list, persons in Canada and Canadians outside Canada are prohibited from engaging in a list of activities in relation to that person.
[3] A person added to the sanctions list may apply to the Minister to have their name removed: Russia Regulations, s. 8(1). In such circumstances, the Minister must decide whether there are reasonable grounds to recommend such removal to the Governor in Council: Russia Regulations, s. 8(2).
[4] Katia and Laura Fridman, the appellants, were added to the sanctions list on May 27, 2022: Regulations Amending the Special Economic Measures (Russia) Regulations, SOR/2022-117 (2022) C. Gaz. II, 2074. They are daughters of Mikhail Maratovich Fridman, himself added to the sanctions list on April 19, 2022, as an "“associate”" of President Vladimir Putin: Regulations Amending the Special Economic Measures (Russia) Regulations, SOR/2022‑84 (2022) C. Gaz. II, 1245. Mr. Fridman is a multi-billionaire and the founder and main shareholder of the Alfa Group, which includes Alfa Bank, an entity also on the sanctions list. The appellants were added to the sanctions list as "“family members”" of Mr. Fridman, an "“associate”".
[5] The appellants applied to have their names removed from the sanctions list, but in each case the Minister decided there were not reasonable grounds to recommend their removal. The Federal Court, through a single set of reasons, dismissed the appellants’ applications for judicial review of the Minister’s decisions. Applying the reasonableness standard of review, the Federal Court found the decisions transparent, intelligible and justified and therefore reasonable: Fridman v. Canada (Foreign Affairs), 2025 FC 493 (per Brown, J.) at paras. 67, 134.
[6] The appellants now appeal the Federal Court’s decision. While accepting that the Federal Court correctly chose reasonableness as the standard of review, they challenge the Federal Court’s application of that standard, advancing several arguments.
[7] Applying that same standard, as I must, I would dismiss the appeals: Northern Regional Health Authority v. Horrocks, 2021 SCC 42 at paras. 10–12; Agraira v. Canada (Public Safety and Emergency Preparedness), 2013 SCC 36 at paras. 45–47.
[8] I cannot agree with the appellants’ submission that the term "“family member”" in paragraph 2(d) of the Russia Regulations should be interpreted as including any unstated limitations that would restrict it to those "“with a sufficient link”" to the foreign state’s actions. The text is clear and unambiguous and contains no such limitations. It requires only that the Governor in Council be satisfied there are reasonable grounds to believe the person is a family member of a person described in another paragraph in section 2 permitting an individual, including an "“associate”", to be listed. In contrast to paragraphs 2(a) and (a.1) in relation to "“a person”", paragraph 2(d) does not contain any criteria circumscribing a "“family member”".
[9] Relatedly, the appellants assert that it is unreasonable not to recommend the removal of their names given the objectives of the Russia Regulations. While not suggesting the Russia Regulations as a whole are ultra vires, the appellants submit that the inclusion of their names on the sanctions list is ultra vires. In doing so, they acknowledge that the decision to add the appellants’ names to the sanctions list was not the subject of the judicial review, and that only the Minister’s decision that there are no reasonable grounds for recommending their names be removed was.
[10] However, the appellants’ argument is that the Special Economics Measures Act only empowers the Governor in Council to make orders or regulations "“in relation to a foreign state”". This, they submit, means that a person may be added to the sanctions list under the Russia Regulations only if there is a "“sufficient link”" between that person and the foreign state. They claim no such link exists for them. In their view more is required than being a family member of an associate of Mr. Putin, such as evidence they support the Russian regime, have assisted or are willing to assist their father in evading sanctions, or have some other meaningful connection to Russia suggesting "“complicity”" with the foreign state.
[11] I am not persuaded.
[12] The stated purpose of the Special Economic Measures Act is to permit the Canadian Government "“to take economic measures ""against certain persons”" in specified circumstances including where "“a grave breach of international peace and security has occurred”" (emphasis added): Special Economic Measures Act, s. 3.1. Section 4, which empowers the Governor in Council to make orders and regulations, echoes the stated purpose in several ways.
[13] The Governor in Council may make orders and regulations only if it is of the opinion that any of the circumstances described in subsection 4(1.1) has occurred: Special Economic Measures Act, s. 4(1). Those circumstances are identical to the circumstances identified in section 3.1, describing the purpose of the legislation, albeit with additional context. Once that condition is met, the Governor in Council may make "“any orders or regulations ""with respect to the restriction or prohibition of any of the activities referred to in subsection (2) ""in relation to a foreign state that [it] considers necessary”" (emphasis added): s. 4(1)(a). Which activities in relation to a foreign state may be restricted or prohibited? The opening phrase of subsection 4(2) tells us: "“any of the following activities, whether carried out in or outside Canada, in relation to a foreign state”". Subsection 4(2) continues with a long list of activities.
[14] The expressions "“with respect to”" and "“in relation to”" are both broad ones. The Supreme Court of Canada has described the expression "“in respect of”" as one that imports the meaning of "“in relation to”", and as "“probably the widest of any expression intended to convey ""some connection between two related subject matters”" (emphasis added): Nowegijick v. The Queen, 1983 CanLII 18 (SCC), [1983] 1 S.C.R. 29 at 39. And the same broad interpretation applies to "“relating to”" or, in this case, "“in relation to”": Slattery (Trustee of) v. Slattery, 1993 CanLII 73 (SCC), [1993] 3 S.C.R. 430 at 445–46. Both broad connecting phrases "“suggest that a wide rather than narrow view should be taken”" of the Governor in Council’s assessment of the regulations that it considers necessary to accomplish the legislation’s purposes: Slattery at 446.
[15] That Parliament intended a broad scope of authority is reinforced by looking at the persons against whom economic measures may be taken, the "“certain persons”" referred to in section 3. Beyond a foreign state, measures may be taken against "“any person in that foreign state, a national of that foreign state who does not ordinarily reside in Canada or a person outside Canada who is not Canadian”": Special Economic Measures Act, ss. 4(2)(a), (e.1); see also ss. 4(2)(b), (c), (e), (h), (i) which refer to "“that foreign state, any person in that foreign state or a person outside Canada who is not Canadian.”"
[16] I accept that "“in relation to”" requires some connection, but I am not persuaded it requires a connection nearly as significant as that the appellants claim is necessary. Given the broad powers conferred on the Governor in Council to make regulations, that the appellants are "“persons outside Canada who are not Canadian”" and are each a "“family member”" of an "“associate”", the Minister’s rejection of the appellants’ ultra vires argument is reasonable.
[17] I am similarly unpersuaded by the appellants’ arguments challenging the reasonableness of the Minister’s interpretation and application of the governing statute and the Russia Regulations based on foreign jurisprudence.
[18] I agree with the appellants that a reviewing court should not be unduly deferential: Makarov v. Canada (Foreign Affairs), 2025 FCA 223 at para. 5. That said, I disagree that the Federal Court was unduly deferential to the Minister.
[19] In this regard, the appellants’ reliance on this Court’s decision in Attorney General of Canada et al. v. Canadian Civil Liberties Association et al., 2026 FCA 6 is misplaced. There, this Court reviewed the Governor in Council’s decision to invoke the Emergencies Act, R.S.C. 1985, c. 22 (4th Supp.). However, the respective provision in the Emergencies Act is "“quite circumscribed”", referring to definitions with objective standards that make it "“more akin to the legal determinations courts make, governed by legal authorities, not policy”": Canadian Civil Liberties Association at para. 171, citing Entertainment Software Association v. Society of Composers, Authors and Music Publishers of Canada, 2020 FCA 100 at para. 34. Accordingly, that provision did not confer unconstrained discretion. Here, in contrast, the Minister’s discretion is "“very wide indeed”": Makarov at para. 8.
[20] As this Court has explained, "“[t]he Minister can recommend that a person be listed on the relatively low standard of ‘reasonable grounds to believe’”" and can recommend delisting "“only on ‘reasonable grounds to recommend’”": Makarov at para. 7.
[21] There is no reasonable ground to believe the appellants are not "“family members”" of Mr. Fridman, an "“associate”". This fact, relied on by the Minister, is not disputed.
[22] The Minister’s decisions also expressly state that she considered the arguments the appellants advanced in support of their delisting, including their financial independence from their father, their opposition to the war in Ukraine, their father’s stated intention to donate his fortune to charity, and the lack of nexus between listing the appellants and the objectives of the sanctions regime. The appellants do not claim that the Minister failed to consider their submissions. However, they claim that given those submissions (including the enclosed evidence) the Minister’s reasons do not justify her decisions.
[23] I disagree.
[24] The Minister’s decisions explain that the aims of listing family members include "“prevent[ing] the circumvention and evasion of sanctions and other restrictive measures”" and "“encourag[ing] behaviour change that could foster resolution of the conflict”" in Ukraine. The decisions then tie the appellants’ listing to those aims: "“preventing sanctions evasion by eliminating options for those supporting or facilitating the Russian regime”" and "“to denounce Russia’s breach of international security”" and "“apply pressure on the Russian regime”". In this regard, the Minister said maintaining limited financial ties with or dependence on their father does not preclude him from attempting to circumvent the sanctions by using the appellants, who acknowledged receiving financial support and gifts from him.
[25] I cannot conclude the Minister’s "“rather unconstrained”" decisions are unreasonable: Makarov at para. 6. Reviewing the entire record, I am satisfied that the Minister considered, evaluated, and weighed the evidence taking into account the purposes of the sanctions regime, and that the reasons are responsive to the appellants’ submissions and the state interests at stake: Makarov at para. 5.
[26] The appellants have not met their burden to establish that the Minister’s decisions are unreasonable: Canada (Minister of Citizenship and Immigration) v. Vavilov, 2019 SCC 65 at para. 100. . Makarov v. Canada (Foreign Affairs)
In Makarov v. Canada (Foreign Affairs) (Fed CA, 2025) the Federal Court of Appeal dismissed an appeal, here brought against the dismissal of a JR refusing to remove the appellant from a Special Economic Measures Act (SEMA) 'sanctions list'.
In this case the court considers a rare SEMA international sanctions list JR:[1] In the discharge of its responsibility over foreign affairs and international relations and in reaction to Russia’s war against Ukraine, the Government of Canada sanctioned the Government of Russia and those associated with it: see the Special Economic Measures Act, S.C. 1992, c. 17 and the Special Economic Measures (Russia) Regulations, S.O.R./2014-58. The Government of Canada, specifically the Governor in Council, was "“of the opinion that the actions of [the Government of Russia] constitute a grave breach of international peace and security that has resulted or is likely to result in a serious international crisis”": Regulations, preamble.
[2] Mr. Makarov became a billionaire from his business activities in Russia, some of which were state assisted, or state associated, with connections, some close, to Russian governmental officials. Thus, the Governor in Council added him to the sanctions list.
[3] Under the Act and the Regulations, Mr. Makarov can ask the Minister of Foreign Affairs to recommend to remove him from the sanctions list, with evidence and submissions in support. This, Mr. Makarov did. The Minister refused.
[4] Mr. Makarov challenged that refusal in the Federal Court. The Federal Court dismissed Mr. Makarov’s challenge, finding the Minister’s decision reasonable: 2024 FC 1234 (per Brown J.). Now Mr. Makarov appeals to this Court. We must dismiss Mr. Makarov’s appeal.
[5] Mr. Makarov contests the considerable deference the Federal Court showed to the Minister given the significant personal impact upon him. We agree with Mr. Makarov that a reviewing court should not be unduly deferential: in this regulatory regime, the Minister must consider, evaluate and weigh both sides’ evidence, decide the matter based on a reasonable view of the legislative standards, and provide reasons responsive to the important personal and state interests at stake. In our view, as the Federal Court found, the Minister did this.
[6] That being said, the Minister’s decision under this legislation—particularly her appreciation of the meaning of an "“associate”" in subsection 2(c) of the Regulations viewed in light of the other subsections, the purposes behind including "“associates”" in this sanctions regime, and whether there are reasonable grounds to believe Mr. Makarov is no longer an "“associate”" and should be delisted—calls at least in part upon intangible, policy-based appreciations resting right at the bullseye of the executive’s high responsibility to manage Canada’s foreign relations, international interests and global affairs. These are fields that draw upon sensitive, impressionistic and imprecise evaluations and assessments that are complex, ever-changing and fraught with expertise. Here, we are in the realm of the quintessentially executive, a matter beyond the ken of the Courts. Thus, overall, the Minister’s decision is rather unconstrained. See Portnov v. Canada (Attorney General), 2021 FCA 171, [2021] 4 F.C.R. 501; Canada v. Boloh 1(A), 2023 FCA 120, at para. 67, citing Canada (Prime Minister) v. Khadr, 2010 SCC 3, at para. 39; Singh Brar v. Canada (Public Safety and Emergency Preparedness), 2024 FCA 114 at para. 17; see also Canadian National Railway Company v. Halton (Regional Municipality), 2024 FCA 160.
[7] This is buttressed by the text of the legislation, always binding upon us absent constitutional concern. The Minister can recommend that a person be listed on the relatively low standard of "“reasonable grounds to believe”" the person is currently an associate of the regime (section 2 of Schedule 1 of the Regulations), the Minister can recommend to the senior policy body in the Government of Canada (the Governor in Council) the delisting of a person only on "“reasonable grounds to recommend”" (Regulations, subsection 8(2)), and the Governor in Council can act on its "“opinion”" (subsection 4(1) of the Act).
[8] This is not to say that the Minister has anything close to an absolute and untrammelled discretion and is somehow exempted from the rule of law: Roncarelli v. Duplessis, 1959 CanLII 50 (SCC), [1959] S.C.R. 121, 16 D.L.R. (2d) 689 at p. 140. But it is to say that the discretion to recommend that sanctions be imposed under a legislative regime like this in circumstances like these, while subject to legal standards, is very wide indeed. Thus, judicial intervention will be rare.
[9] Many of Mr. Makarov’s submissions use the language of legal principle. But, in reality, Mr. Makarov asks us to reweigh the evidence and redo the Minister’s job. Indeed, Mr. Makarov goes further. He asks us to make our own decision and impose it on the Minister. Under reasonableness review and the granting of remedies, this is not our normal task: Canada (Minister of Citizenship and Immigration) v. Vavilov, 2019 SCC 65, [2019] 4 S.C.R. 653 at para. 125.
[10] In this case, we cannot say that the Minister’s decision is unreasonable, especially given the ample and detailed record supporting the Minister’s decision. Among other things, Mr. Makarov was heavily involved in Russian gas sectors through his company, ITERA. He was connected to Russian oligarchs and controllers of Russian state-sponsored and state-owned companies. As well, he was a senior sports official in Russia and had dealings with the Russian President, Vladimir Putin.
[11] Before the Minister, Mr. Makarov adduced limited evidence and argued that he is no longer an associate of the Russian regime. He says he was forced to sell his oil and gas business, ITERA; he renounced his Russian citizenship; his relationship with certain figures was adversarial. He also says he has never been politically involved and that he does not currently support President Vladimir Putin. He says he has spoken against the Ukraine war and has made humanitarian contributions to vulnerable Ukranians.
[12] Given the limited evidence, the Minister considered Mr. Makarov’s attempts to distance himself from the Russian regime to be superficial, not meaningful. The Minister found that nothing really changed between the decision to list Mr. Makarov, which was supported by a constellation of evidence of association, and his application to be delisted. The Minister did not consider Mr. Makarov’s renunciation of citizenship a genuine effort to separate himself from the regime. He had not publicly denounced the Government of Russia or President Vladimir Putin, something that might help to rebut his past associations and activities. As well, the Minister found the extent of Mr. Makarov’s humanitarian efforts difficult to substantiate. The Minister considered the purposes of this sanctions regime, drew upon an appreciation of international affairs, noted the decisions of other states to sanction Mr. Makarov, and concluded that Mr. Makarov had not made out a case for delisting. On the evidence, bearing in mind the nature of the decision and this legislative regime, this was open to the Minister.
[13] As well, we note that Mr. Makarov has properly admitted (at para. 83 of his memorandum) that "“evidence of a past association could be circumstantial evidence of a current association”". Viewing the entire record, we consider that this idea was very much part of the Minister’s decision that in the circumstances Mr. Makarov had to do more to distance himself from the regime to be delisted.
[14] Mr. Makarov asks this Court to interpret the word "“associate”" in the Regulations narrowly and precisely. In this Court, he argues that "“associate”" requires a closeness that the Minister cannot demonstrate in this case and he relies mainly on dictionary definitions of "“associate”".
[15] But Mr. Makarov, then represented by different counsel, did not make submissions to the Minister on the interpretation of "“associate”", including its text, context and purpose. Under this legislative framework, the Minister—not the reviewing courts—is the merits-decider on all issues, including issues of legislative interpretation: Association of Universities and Colleges of Canada v. Canadian Copyright Licensing Agency (Access Copyright), 2012 FCA 22, 428 N.R. 297; Delios v. Canada (Attorney General), 2015 FCA 117. For that reason, as the Federal Court said, reviewing courts lean against hearing legislative interpretation arguments for the first time on judicial review: Alberta (Information and Privacy Commissioner) v. Alberta Teachers’ Association, 2011 SCC 61 at paras. 24-25. Here, to interfere with the Federal Court’s discretion not to hear Mr. Makarov’s legislative interpretation arguments, we must find palpable and overriding error, a high standard indeed: see, e.g., Mahjoub v. Canada (Citizenship and Immigration), 2017 FCA 144. Here, Mr. Makarov has fallen way short of the mark. Indeed, we would have exercised our discretion like the Federal Court did. However, were we to consider the issue of legislative interpretation, we would not be persuaded that the Minister adopted and applied an unreasonable interpretation of "“associate”".
[16] Mr. Makarov also submits that the Minister ignored the harsh consequences of his listing. But the mere non-mention of something in the Minister’s reasons does not necessarily mean the Minister did not consider it. In any event, the Minister’s reasons viewed in light of the record show due appreciation of the important interests at stake.
[17] The Minister’s decision was made based on evidence existing at the time of this decision. If there is new evidence such that the legislative threshold of a "“material change in circumstances”" is met, Mr. Makarov can apply again to the Minister and the Minister must consider the matter afresh: Regulations, subsection 8(5).
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