Strategy has spent recent weeks repurchasing bitcoin it sold over the summer, and the round trip has proved costly. After selling low between May and August and buying back high this autumn, Michael Saylor's company — the largest corporate holder of bitcoin, until recently known as MicroStrategy — has incurred an opportunity cost of more than $100 million on the trade.

Despite years of assurances that it would never sell, Strategy sold 6,948 BTC between May and August at an average of $62,150 per coin, according to a report by Protos. It has since repurchased 5,553 of those coins at an average of $80,207. In effect, the company ended up holding the same 5,553 bitcoin it started with, but paid $445.4 million to replace coins it had sold for $345.1 million — a 29% premium that amounts to a foregone $100.2 million investment gain while the company was out of the market during a bitcoin rally.

The sales were framed largely as a messaging exercise rather than a response to a shortage of cash. On a May 5 call with analysts, Saylor said the company would sell BTC "just to inoculate the market" and generate headlines confirming that it had done so. He told Fortune, "the skeptics and the short-sellers don't recognize that we're just selling a BTC derivative, and we have the option to sell the BTC." Saylor and CEO Phong Le made numerous television and podcast appearances explaining that the initial sale was for messaging purposes, and the official SEC filing (Form 8-K) for the sales stated that proceeds funded dividends — even though the company held ample cash to cover those payouts without selling bitcoin. The $100.2 million gap effectively puts a price tag on that messaging exercise.

The Buyback

Strategy's first re-buy of the year came in the week ending August 30, when it purchased 4,603 coins at $80,318 each for a total of $369.7 million It was the company's first purchase in 10 weeks and was funded with newly issued stock, diluting common shareholders — the equity-issuance mechanism Strategy has relied on for years to build its treasury, and one that spreads the cost of any trade across existing holders. Last week, it repurchased another 950 BTC at $79,670 apiece, this time using cash instead of outright stock dilution. Every coin came back roughly $18,000 more expensive than its average sale price.

The replacement remains incomplete. Strategy has paid about $445 million to reacquire 5,553 coins, but 1,363 coins are still missing from its treasury. The company holds 846,000 BTC today — roughly 4% of bitcoin's capped 21 million supply — down from 847,363 as recently as June 21, and buying back the remainder would require roughly another $100 million at current bitcoin prices. How the company closes that remaining gap, and whether it turns to stock issuance or cash as it did this autumn, will be visible in its week-to-week purchase disclosures.

Nobody at Strategy has apologized for the outcome. Saylor has been unapologetic, and Le, posting on the day of the company's fourth sale of the year, wrote: "This is the Digital Credit Capital Framework at work." He later told Bloomberg that it was "the right trade at the time to sell BTC."

"It's a two-way strategy," Le added, unfazed by criticism. "There will be times when it makes sense to sell bitcoin."