Trump’s July Trades Put Tax-Loss Harvesting Under Scrutiny

A sale of as much as $25 million in Microsoft shares, followed three days later by a smaller purchase, is not enough to show that President Donald Trump’s portfolio harvested a tax loss. The filing reports transaction values, not what the shares originally cost or whether the sale locked in a loss.

Trump’s July disclosure, released by the U.S. Office of Government Ethics, lists 1,156 securities transactions. CNBC’s tally put their combined value between about $79 million and $270 million. Among the largest entries: sales of $5 million to $25 million each in Microsoft and Amazon on July 20. On July 23, the accounts reported buying $100,001 to $250,000 in Microsoft and a smaller amount of Amazon.

A spokesperson for Trump’s family told CNBC that third-party firms manage the accounts and engage in daily tax-loss harvesting. The filing itself does not explain the trades or confirm that the Microsoft sale was part of that strategy. The distinction matters: a sale can be tax-motivated, but without the cost basis and account-level details, outsiders cannot tell whether it realized a loss.

Tax-loss harvesting generally means selling an investment below its purchase price to realize a loss that can offset capital gains in a taxable account. The IRS allows qualifying net capital losses above gains to offset up to $3,000 of ordinary income for most individual filers, with unused losses carried forward. There’s a catch. Buying substantially identical shares within 30 days before or after a loss sale can trigger the wash-sale rule, deferring the deduction.

That rule puts the July 23 Microsoft purchase in view, but it does not settle the question. The public disclosure gives broad dollar ranges, not share counts, purchase prices or a full lot-by-lot account history. The repurchase might involve different lots or reflect other portfolio decisions; the document does not say.

For ordinary investors, the strategy is most relevant in taxable accounts with realized gains to offset. It does not create a tax-loss benefit inside a 401(k) or IRA. And copying a high-profile account’s trades from delayed disclosures is no substitute for knowing your own cost basis, tax situation and wash-sale exposure. In this case, the headline strategy is a reported explanation, not a conclusion the filing proves.