Greig v Commissioner of Taxation [2020] FCAFC 25

TAXATION – allowable deductions – where taxpayer made 64 separate acquisitions of shares in one company – whether the taxpayer’s acquisition of shares was made in a “business operation or commercial transaction” within the meaning of the principle established in Federal Commissioner of Taxation v Myer Emporium Ltd [1987] HCA 18; (1987) 163 CLR 199 – whether loss or outgoing was incurred in gaining or producing assessable income – whether the shares had been held by the taxpayer on revenue account – whether the shares were purchased in circumstances which were akin to, or indistinguishable from, an ordinary investment engaged by a private investor TAXATION – whether legal fees and share losses incurred by the taxpayer by reason of the compulsory transfer and cancellation of his shares were deductible under s 8-1 of the Income Tax Assessment Act 1997 (Cth)

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