Your client, White Corporation, has done well since its formation 20 years ago. This year, it recognized a $50 million capital gain from the sale of a subsidiary. White's CEO has contacted you to discuss a proposed transaction to reduce the tax on the capital gain. Under the proposal, White will purchase all of the common stock in Purple Corporation for $200 million. Purple is a profitable corporation that has $63 million in cash and marketable securities, $137 million in operating assets, and approximately $280 million in E & P.
After its acquisition, Purple will distribute $50 million in cash and marketable securities to White. Due to the 100% dividends received deduction, no taxable income results to White from the dividend. White then will resell Purple for $150 million.
The subsequent sale of Purple generates a $50 million capital loss [$150 million (sale price) - $200 million (stock basis)]. The loss from the stock sale can then be used to offset the preexisting $50 million capital gain. Will the proposed plan work? Why or why not?