On February 23, 2021, the Tax Court issued a Memorandum Opinion in the case of Anikeev v. Commissioner (T.C. Memo. 2021-23). The primary issue presented in Anikeev v. Commissioner was whether the “rewards” earned from the purchase of gift cards…a lot of gift cards…were income. Background to Anikeev v. Commissioner The petitioners were crafty Russians, who gamed the credit card reward system.  They joined a credit card rewards program and proceeded to purchase their credit limit worth of prepaid gift cards.  With the gift cards, they bought money orders, and with the money orders deposited in their bank accounts, they paid off the credit cards.  This process cost, on average, $6, whereas they could make anywhere from $5 to $25 on each purchase. In 2013, the petitioners charged $1,219,077 on their credit card, $1,208,376 of which was used to purchase gift cards.  In 2014, they spent $5,184,033 on gift cards. …