By Mackenzie Tatananni

As Bitcoin hovered below $60,000 on Friday, the world's largest corporate holder of the cryptocurrency was weathering its own tailspin.

Strategy looked set to extend its record losing streak on Friday, one day after the software company-turned-Bitcoin holder suffered its longest stretch of consecutive daily declines since January 2024.

Over the latest seven-day stretch, Strategy has lost nearly 35% -- its worst performance since the seven days ended Nov. 16, 2022, according to Dow Jones Market Data. If shares continue to fall, they will break that record and suffer their longest losing streak since December 2022, when they fell for 10 consecutive trading sessions.

Strategy's latest woes are tied directly to a slump in its Stretch preferred stock (STRC). The company has long relied on this high-yielding equity as its primary engine to bankroll Bitcoin acquisitions -- a strategy that backfires when the shares lose ground.

When STRC trades around or exceeds its par value of $100, Strategy can easily generate capital by issuing new shares to buy more Bitcoin. However, STRC has been sliding further away from that target price, hitting a record low of $73.62 this week.

This steep discount severely limits Strategy's ability to issue new preferred capital to fund its Bitcoin purchases. It could also force the company to increase Stretch's already hefty 11.5% annual dividend.

The cash-for-crypto machine rolls on, though not without cost to ordinary investors. The company disclosed Monday that it had used proceeds from common stock sales to purchase Bitcoin and pad its cash reserves in the preceding week.

The move solves an immediate headache by covering Strategy's preferred dividend obligations, but it does so through the painful, if familiar, route of diluting common shareholders.

Bitcoin is enduring its own slump. The price of the world's largest crypto by market capitalization was rebounding slightly on Friday, though it remained below $60,000. Bitcoin fell as low as $58,065 Thursday, its lowest intraday level since September 2024.

Bitcoin has taken a hit as an ongoing rout in tech stocks pulls risk assets lower. Investor concerns only intensified after Apple hiked prices for some of its major products on Thursday, citing the rising cost of memory and storage chips. The move sparked broader fears about the sustainability of the AI boom.

Write to Mackenzie Tatananni at mackenzie.tatananni@barrons.com

This content was created by Barron's, which is operated by Dow Jones & Co. Barron's is published independently from Dow Jones Newswires and The Wall Street Journal.

(END) Dow Jones Newswires

June 26, 2026 08:54 ET (12:54 GMT)