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Saylor’s Bitcoin Machine Picks Up Bonds, Not Bitcoin — Wall Street Notices

New York, May 26, 2026, 08:04 EDT

Strategy Inc. stopped buying bitcoin this week, shifting focus to repurchasing its 2029 convertible notes. The move is unusual for Michael Saylor’s bitcoin vehicle, which has been on a buying streak. Saylor posted on X, “This week we bought bonds, not bitcoin.” Cryptonews

Strategy is now the main public-market stand-in for bitcoin demand. A week ago, the company added 24,869 bitcoin for $2.01 billion, putting its stash at 843,738 tokens. That’s now over 4% of the fixed 21 million bitcoin supply.

Strategy is turning to funding rather than accumulation. In a filing, the company said it will buy back roughly $1.50 billion of its 0% convertible senior notes due 2029, paying an estimated $1.38 billion in cash. Convertible notes give holders a right to swap debt for shares under certain terms.

The company said it plans to pay for the buybacks with cash it already has, money from at-the-market stock offerings, or by selling bitcoin. The filing didn’t say if any bitcoin had been sold.

Strategy kept buying last week. It got about $1.95 billion from selling 19.5 million STRC preferred shares and collected another $83.7 million from selling 430,344 class A shares. The funds went toward bitcoin, with the firm paying an average of $80,985.

TD Cowen is sticking with its Buy on Strategy and bumped up its price target to $400, up from $395. The bank pointed to strong treasury activity and a balance-sheet change after Strategy bought back notes at a discount. “Strategy’s treasury operations continue to exceed expectations,” analysts Lance Vitanza and Jonnathan Navarrete said in a summary of the note. crypto.news

TD Cowen raised its forecast for Strategy’s 2026 BTC Yield, which tracks how much bitcoin the company holds per diluted share. The bank now sees around 100,000 bitcoin bought in the second quarter, up from its earlier projection. It set bitcoin per 1,000 fully diluted shares at 2.21, versus 1.95 at the close of 2025.

Strategy shares changed hands at $159.89, off about 3% with bitcoin near $77,100. The stock trades well under TD Cowen’s target, leaving a gap that points to how much depends on steady capital market access and stronger bitcoin pricing.

No listed competitor comes near in size. BitcoinTreasuries.net puts Strategy above Twenty One Capital, Metaplanet, and MARA Holdings, showing those three with about 43,514, 40,177 and 35,303 bitcoin each. That’s why even a one-week halt from Strategy can swing sentiment on corporate treasury demand.

Strategy’s top brass aren’t changing their tune. CEO Phong Le told investors earlier this month, “Adoption of Bitcoin continues to grow in 2026,” after the company posted a first-quarter net loss of $12.54 billion. The loss came from a $14.46 billion unrealized loss on digital assets. Strategy

But risks are still there. Strategy said in its annual filing it may need to sell shares or bitcoin to raise cash if its convertible notes come due or are redeemed without being converted, or if it buys back other debt. That could lower bitcoin-per-share and dilute holders.

Right now, the bond buyback is more about cleaning up the balance sheet after a big purchase, not a shift away from bitcoin. The next filing will tell if this is just a one-week break or if Strategy keeps using its market firepower on its liabilities and not just coins.

Khadija Saeed is a financial markets reporter at TS2.tech, specializing in stocks, technology and emerging industries. She studied economics and finance at the London School of Economics and previously worked in market research before moving into financial journalism. Her coverage focuses on the companies, innovations and economic trends influencing global investors.

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