Strategy Moves 411 BTC to Coinbase Prime as Polymarket Sell Odds Hit 84%

Strategy’s Move Raises Sell Fears

Strategy (formerly Microstrategy), the largest corporate holder of bitcoin, moved 411.48 BTC worth about $30.3 million into Coinbase Prime on May 29, according to onchain trackers. Analysts flagged the transfer as the company’s first direct deposit to an exchange-linked platform in nearly two years, immediately reviving speculation that executive chairman Michael Saylor’s firm could be preparing to sell.

That said, the deposit alone does not confirm a sale, given that large corporate holders routinely shift coins for custody, collateral, rebalancing, or settlement without liquidating a position. But the timing of the development, i.e. during a weeklong bitcoin slide, has been enough to lift the odds of a Strategy bitcoin sale before Dec. 31, to 84% on the decentralized prediction market Polymarket.

A Dividend Bind, Not Just a Transfer

The deposit landed as Strategy faces fresh scrutiny over how it is financed, as Jeff Dorman, chief investment officer at digital-asset manager Arca, wrote on May 28 that the MSTR story had “gotten out of hand,” pointing to roughly $15 billion in outstanding perpetual preferred stock that carries about $1.5 billion in annual dividend obligations.

Those preferred shares, issued under tickers such as STRK, STRF, STRD, and STRC, were sold aggressively on expectations of a major bitcoin rally, Dorman argued. The warning lands against a jittery backdrop, given that U.S. spot bitcoin exchange-traded funds (ETFs) have bled cash for days, and bitcoin has slipped well below its all-time high.

Strategy has met every distribution so far, paying out hundreds of millions of dollars across more than 20 consecutive payments since early 2025. The open question is what happens if bitcoin keeps falling and dividend coverage tightens.

Why a Sale Would Sting

Strategy’s stockpile stood at 843,738 bitcoin earlier this week, by far the largest of any public company. A forced sale from that position would not only dent the firm’s own balance sheet; it could add heavy selling pressure to a market already on the back foot, hammering the price of the very asset that underpins Strategy’s equity story. Dorman framed it as a three-sided “bind” between the company, bitcoin, and preferred shareholders.

Saylor has fueled the debate himself since, in recent weeks, the chairman has floated selling a fraction of the stack to help service dividends, a striking shift for an executive who built his reputation on a “never sell” ethos and near-weekly purchases.

For now, the 411 BTC sitting in Coinbase Prime remains just a transfer, not a trade. Whether it marks the start of Strategy’s first-ever bitcoin sale or routine treasury housekeeping will likely hinge on the price action ahead and on how comfortably the company can keep covering its dividend bill. Traders, judging by Polymarket, are bracing for the former.