Bessent and Saylor are running versions of the same playbook.
A 30-year Treasury issued in 2022 now trades at a meaningful discount to par. The basic trade is obvious: issue short-term debt and use the proceeds to repurchase long-duration bonds below par. It is straightforward balance-sheet management, not rocket science.
Saylor and MicroStrategy apply the same logic in capital markets: issue equity, then repurchase preferred securities trading below par. When the liability can be retired at a discount, the economics are compelling.
Yet Wall Street often misses the most basic back-of-the-envelope analysis.
He previously labeled the same strategy a failure.https://t.co/CNvEI190Nh
— New Low Observer (@NewLowObserver) August 20, 2026
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— Taylor Kenney (@taylorkenneyitm) August 19, 2026