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. … Considering the complexity of Mr. Goldhar’s businesses and his lack of tax expertise, it is my view that he took all reasonable steps that a wise and prudent person would to ensure that his tax returns were filed properly during the taxation years under appeal. … Mr. ...

. … Before so concluding, he stated (at paras. 137-138): [The] history of the definition of RDTOH shows that Parliament intended for the refundable tax regime for Part I tax, which now includes section 123.3, to only apply to CCPCs. … In my view, the text, context and purpose of section 123.3 does not support a finding that its object, spirt and purpose was to prevent Canadian resident individuals from deferring tax on investment income held in any private corporations. ...

. … [T]he mischief targeted by s.160, avoidance of payment of a tax debt to the Crown, has also not occurred. ... Its bank account, working capital, other assets and reserves have not been depleted in any way …. ...

In rejecting the “sham” submission, Sommerfeldt J stated (at para. 82) that he “did not find anything to suggest that the … Documents did not accurately set out the legal rights and obligations that Mr. ... Regarding the legal effectiveness of the trades, he noted that although it was unclear which jurisdiction’s laws governed the agreements, all of these jurisdictions were common-law jurisdictions and concluded (at para. 107) that “[b]ased on the evidence and [his] understanding of the fundamental common‑law principles of contract law … the FX Contracts were legally effective, in accordance with their terms.” ...

Also in March 2005, 9149 redeemed the Class A common shares for their PUC and ACB of $347,848 (so that no deemed divided or capital gain resulted) and redeemed approximately ¾ of the Class B preferred shares, giving rise to a deemed dividend and capital loss of $196,506 to the taxpayers. ... At the end of 2008, 9149 redeemed the (¼) balance of the Class B preferred shares for $69,000, giving rise to a deemed dividend and capital loss to the taxpayers of $69,000 and $73,112. ... Furthermore, there was no change in Oka's real estate business until the sale nine months after the alleged distribution (step 5), and its real estate business did not cease for a further year – whereas s. 84(2) required such a change to occur contemporaneously with the distribution. ...

In this regard, Hogan J stated (at paras. 157-8 and 160): … I infer that the Appellant honestly believed that the shares of MDPC could be valued under the income approach…. ... Van Essen acted imprudently in failing to disclose the pending sale of MDPC to his colleague, I do not believe that the Appellant can be held accountable for his actions. … It is well established that a taxpayer is responsible for the actions of his agent only where the taxpayer is privy to the gross negligence of that agent or wilfully blind to the fact of that negligence and the taxpayer acquiesces or participates in the false statements or omissions. ... More generally, he had stated (at paras. 146-7): Skilled tax advisors and the CRA have difficulty identifying where the boundaries of anti-avoidance provisions lie. … Courts have generally been reluctant to apply gross negligence penalties where a taxpayer relied in good faith on the advice of tax professionals, or where all relevant amounts were disclosed in tax returns. ...

In finding that these hedging criteria were not satisfied, so that his settlement payments under the Forward Contract were fully deductible, she stated (at paras 107 and 112): … [T]he settlements were not based on any anticipated sale of the BNS shares and the sale of BNS shares by Mr. ... MacDonald owned the BNS [and predecessor] shares for approximately 30 years prior to entering into the Forward Contract. … Mr. ... MacDonald had mitigated or reduced a risk. … The fact that the taxpayer also received a TD loan (which was much less than the maximum he could have borrowed and was largely repaid by 2004) was of limited relevance. ...

. – of which 3.75% of p.a. was required to be paid annually in cash (“cash-pay interest”) and with the balance was capitalized each year (“capitalized interest”). ... He stated (at para. 345): [T]he phrase bona fide speaks to the fundamental character of the arrangements and requires that the arrangements reflect what one would reasonably expect arm’s length commercial relations to look like in the circumstances. … After noting that the taxpayers had not disclosed their debts incurred from their previous participation in tax shelters, he stated (at paras. 352-4): In my view, a borrower’s unilateral determination that a significant liability need not be disclosed on a loan application coupled with the failure of FT to insist on full disclosure is strong evidence of an absence of the sort of good faith and genuineness contemplated by paragraph 143.2(7). ... I also draw a negative inference … from... no one from FT testif[ying] regarding the borrowing arrangements with the Participants. ...

Under the investment component: The taxpayer purchased a minimum of 10 limited partnership units (the “LP Units”) in an Ontario limited partnership (the “2009 LP” – whose general partner was owned by a family trust of the owner of the promoter (“EquiGenesis”)) for $36,140 per LP unit, of which $32,000 was funded by a loan (a “Unit Loan,”) – which had a maturity date in February 2019, was secured by a pledge of the LP Units, bore interest at 7.85%, all of which in fact was funded with further cash advances from the lender (“capitalized interest”), who was a trust (“FT”)- and the balance was funded by the taxpayer. ... The approach taken in each of paragraphs 7000(2)(a) through (d) is consistent with the general proposition that an amount is not recognized as income under the ITA unless the amount can be ascertained with some reasonable degree of certainty. … In the absence of an actual crystallizing event there is simply no way of knowing the actual amount that the 2009 LP is entitled to be paid under the terms of the Linked Notes and therefore there is no amount to reallocate to avoid a deferral of income. ...

Immediately after the Partnership’s first fiscal year end, the taxpayer’s share of the capital gain from the sale increased the ACB of its Partnership interest by $24.3M, and its CDA by ½ thereof, or $12.2M (or, in fact, $11.7M taking Partnership operating losses into account). ... Hogan J concluded (at para. 85), in confirming the Minister’s application of s. 245(2) to reduce the taxpayer’s CDA by ½ the amount of the s. 40(3.1) capital gain (thereby generating Part III tax subject to a s. 184(3) election being made): [T]he GAAR applies because the Avoidance Transactions were specifically designed to achieve a result that was, in the case of subsections 40(3.1) and 40(3.12), inconsistent with the rationale underlying each of those provisions and equally inconsistent with the rationale of the provisions that form part of the CDA Mechanism …. ...