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Unless he dies or loss is from realised earn-out
Capital losses cannot be carrried back, except for losses made in the year of death, when they may go back three years. So 2008 is out of reach.
A loss made on the realisation of a right such as an earn-out, may be set against the taxation of the original earn-out right. See chapter 3 of the Bloomsbury Professional core tax annual on captial gains tax. The 2014/15 vedition has enough detail.