BTC sale and repurchase timing raise wash sale issue, Andy Constan notes

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Daria Chernytska

01.06.2026

BTC sale and repurchase timing raise wash sale issue, Andy Constan notes — Strategy BTC sale may trigger wash rule

Andy Constan, founder / strategist at Damped Spring Macro, examines Strategy's decision to sell some BTC. Constan initially viewed the sale as a strategic move to realize a taxable loss given the high purchase price of BTC by the company.

However, he questions whether the benefit can be realized if Strategy repurchases BTC within 31 days, citing the wash sale rule. Constan asks if his understanding is correct that buying BTC again too soon may negate the tax benefit of the loss.

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Constan has previously highlighted macroeconomic trends, noting that U.S. national debt grew from $1 trillion to $39 trillion over 46 years. In another update, he reported losses on SPX and NDX puts but gains in bonds, describing current risk as low. These updates reflect Constan’s ongoing tracking of market shifts and risk positions.

This material may contain third-party opinions, none of the data and information on this webpage constitutes investment advice according to our Disclaimer. While we adhere to strict Editorial Integrity, this post may contain references to products from our partners.

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