MicroStrategy's Saylor Declares Bitcoin Bear Market Over, Eyes Return to $100K

Michael Saylor, the co-founder and executive chairman of corporate Bitcoin holder MicroStrategy (MSTR), has declared an end to the cryptocurrency's bear market. Citing Bitcoin's recent rebound to the $83,000 level, Saylor predicted the digital asset would soon reclaim six-figure territory.

"It certainly should return to the six-figure, over $100,000," Saylor said in a Tuesday interview with Bloomberg Television. "We bottomed somewhere just shy of $60,000, and I think we've bounced off of that... I think we go higher from here." Bitcoin remains approximately 30% below its previous all-time high of $126,251, reached in October 2025, according to the source.

Strategy Shifts for a New Cycle

MicroStrategy's famous "financing flywheel" strategy—issuing equity and debt to fund Bitcoin purchases—is being adapted for what Saylor sees as a new bull market. During the downturn, the company adjusted its capital framework, at times selling Bitcoin to repurchase dividend-paying preferred stock and reduce leverage. This balance sheet management continues even as the company resumes buying.

• Between October 5-11, MicroStrategy purchased 250 BTC for $21.5 million, bringing its total holdings to 848,250 BTC.
• In the same week, the company spent $192.4 million, about nine times its Bitcoin outlay, to buy back its STRC preferred shares.
• This follows a similar move in August, when it sold 1,690 BTC for $108.6 million to fund share repurchases, reducing future dividend obligations.

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Saylor indicated the company would likely ramp up its purchasing strategy again. "We're entering a bull market, so I would expect that we'll probably be buying Bitcoin and issuing credit-type securities in the bull market," he stated.

A Looming Index Threat

Despite Saylor's optimism, MicroStrategy faces a significant headwind from index provider MSCI. The firm is considering new rules that could exclude companies primarily engaged in asset accumulation rather than operating a core business. Such a change could force MicroStrategy out of MSCI's global stock benchmarks, potentially triggering a significant sell-off from passive funds.

A November estimate from JPMorgan suggested that as much as $2.8 billion in funds could be at risk of outflows if the company is delisted. This would put pressure on MicroStrategy's stock price and could increase the cost and dilutive effect of future capital raises, threatening the efficacy of its Bitcoin acquisition model. Saylor criticized the potential move, stating, "We think their position so far is disappointing because they're imposing a biased value judgment on digital assets." MSCI is expected to announce its decision on Friday.