Famed short seller Jim Chanos closed his closely-watched wager pitting Strategy against bitcoin , saying the valuation gap that once made the trade so compelling had largely vanished. Chanos said Saturday in a social media post on X that as of Friday’s market open he had unwound his pair trade of shorting Strategy and going long bitcoin . The move came after Strategy shares plunged about 50% from their 2025 peak, erasing much of the premium investors were once willing to pay for its massive bitcoin holdings. The software company has bought billions of dollars worth of bitcoin in recent years, becoming the largest corporate holder of the flagship cryptocurrency. Strategy, formerly MicroStrategy until earlier this year, used leverage to amass its bitcoin stockpile and once traded at a wide premium to its bitcoin holdings. MSTR YTD mountain Strategy shares year to date Chanos referenced Strategy’s market-implied net asset value, or mNAV, a metric that compares the market value of a company to the value of the assets it holds. In Strategy’s case, that’s almost entirely bitcoin. When Chanos first recommended the trade privately at his Bears In Hibernation Conference in December 2024, Strategy’s mNAV was closer to 2.5x, meaning investors were paying about $2.50 for every $1 of bitcoin that Strategy owned. Since then, Strategy’s common stock has fallen even as bitcoin has stayed near record highs, shrinking the excess value built into Strategy shares. Mirroring the slide in Strategy shares, the mNAV multiple has since narrowed to about 1.2, Chanos explained. “While we still believe there is more room for further mNAV compression, the thesis has largely played out,” he told Chanos & Co. clients. “It is prudent to cover this trade with mNAV below 1.25x, having dropped from ~2.0x as recently as July 2025.” The renowned short seller, best known for shorting Enron a year before its collapse in 2001, converted his hedge fund to a family office and advisory business in late 2023. “The premium should continue to compress over time as MSTR continues to issue common equity, but we recommend letting others chase the last leg of the trade as MSTR inevitably marches toward a 1.0x mNAV,” Chanos & Co. wrote in a note attached to Chanos’s social media post.
