Strategy Inc.’s recent sale of 32 Bitcoin drew attention not because of its size, but because of what it signaled to a market already under pressure. Market-making firm Wintermute said the sale mattered as a psychological turning point, coming after weeks of weakening Bitcoin demand, retail investors shifting toward equities, and a more bearish stance among U.S. institutions. The firm said the transaction effectively removed one of the last reasons for bulls to stay confident, especially as Strategy had become a lingering overhang for the market over the previous month.
Wintermute’s weekly market update described a broad softening in crypto flows. On its OTC desk, retail investors had been net sellers for several weeks, while U.S. institutions had turned bearish in recent days. By contrast, demand from Asia and Europe was more balanced. The pressure was also visible in ETF flows, with May recording $2.43 billion in net outflows, the worst monthly reading of 2026 so far.
The macro environment added to the weakness. The U.S. economy added 172,000 jobs in May, well above the expected 80,000, and April’s figures were revised higher. Job openings rose to 7.6 million, the highest level in nearly two years, while the ISM services prices index climbed to its highest point since August 2022. At the same time, the 10-year Treasury yield advanced to 4.55%. Wintermute said this created a “good news is bad news” backdrop, because stronger economic data reduced hopes for near-term Federal Reserve rate cuts and kept financial conditions restrictive.
Risk assets reacted accordingly. The Nasdaq fell 4.7% for the week, and the S&P 500 posted its first weekly loss since March. Crypto and artificial intelligence-related stocks both came under pressure as investors reassessed expectations for easier monetary policy.
Still, not everyone viewed the pullback as purely negative. Bitcoin advocate Anthony Pompliano said on CNBC that the current downturn may be one of the shallowest bear markets in Bitcoin’s history. He pointed to a key market metric showing that the share of Bitcoin held at a loss has now exceeded the share held at a profit, a pattern that has historically appeared near cycle lows.
Pompliano also argued that Strategy and Strive have built structural protections against forced Bitcoin selling by holding dollar reserves intended to cover dividend obligations. In his view, those cash buffers reduce the chance that either company would need to sell Bitcoin during a downturn.
The report reflects a market caught between weakening crypto sentiment, stronger-than-expected macro data, and debate over whether the recent decline is a deeper breakdown or a cyclical reset.
