Strategy’s Dream Hangs On A 23% Tightrope—Can It Stick?
Strategy’s activities attract eyeballs whenever there’s movement in Bitcoin (BTC) price, for good reason. Bitcoin price rocketed to $108,786 on January 20, 2025, as Donald Trump stepped back into the White House. Champagne pops at Strategy (formerly MicroStrategy), Michael Saylor’s Bitcoin-obsessed firm, with a comfy 73% cushion above its $62,691 cost basis. Fast forward to March 18, 2025—BTC trades at $81,600, a 24.9% drop. That cushion? Now a slim 23% above the updated $66,360 cost basis. Strategy’s Strategy: A Cushion Cut Thin Michael Saylor’s Strategy, clutching 499,226 BTC bought at $66,360 per coin, is staring down a tightening 23% buffer as Bitcoin dips to $81,602.25 on March 18, 2025. Now, the firm’s rolling out a bold $21 Billion fundraising gambit via five million Series A preferred shares—$STRF—packing a 10% dividend kicker. It’s a high-wire act to bulk up its Bitcoin hoard, but with memecoins, tariffs, and a shaky market in play, can Saylor’s latest move hold firm? Rewind to 2021 or mid-2024—BTC often traded double Strategy’s cost basis, giving Saylor breathing room. Today, that room’s shrinking fast. Since Trump took office, Bitcoin’s lost nearly 50% of Strategy’s cushion, dropping from a 50% margin year-to-date. Saylor’s Buy BTC Strategy is Yet to Get Trump’s Support Strategy’s recent BTC purchases tell a rough story. On November 18, 2024, the firm snagged 51,780 BTC at $88,627 per coin. Four more buys topped $100,000 each, per filings through March 2025. With BTC now at $81,600,those coins are underwater. The spree jacked Strategy’s cost basis from under $40,000 in early November 2024 to $66,360 today. That’s a whopping 65% jump in four months. Each red-ink purchase tightens the rope Saylor walks. Bitcoin price’s slide aligns with Trump’s presidency. Since January 20, 2025, the president has pushed memecoins over Bitcoin, ignored Saylor’s 4 million BTC reserve idea, and rejected Senator Cynthia Lummis’ 1 million BTC plan. His tariff policy shifts have also rattled markets, dragging BTC down. Strategy’s share premium—how much investors pay above its BTC holdings—tells the tale. It has crashed from 3.4X on November 20, 2024, to 1.8X on common shares today, a 47% drop. Trump’s tariff wars have financial markets—and Strategy stock—reeling. Strategy’s $21 Billion Question Mark Saylor’s fighting back. On March 10, 2025, he announced a $21 Billion BTC buy via preferred share sales. As of writing this report, he spent less than $1 Billion. Strategy’s counterpunch came March 18, 2025: a plan to sell five million Series A preferred shares—$STRF—with a 10% annual dividend starting June 30, 2025, per the announcement. Goal? Raise $21 Billion for “general corporate purposes,” mainly Bitcoin buys, subject to market conditions. Source: Michael Saylor/X Earlier this month, Saylor flagged this in an at-the-market (ATM) program, per filings. But execution is slow—yesterday’s 130 BTC buy at $81,600 was a measly $10.6 Million, the second smallest ever. This is just ahead of the 32 BTC scoop in March 2024. Compare that to November’s 51,780 BTC grab.