Strategy’s Preferred Stocks: The Ultimate Guide to Getting Paid First (Or Last!)

Imagine a world where stocks are like the cast of a reality show—some get to sit in the front row, others are sent to the back, and a few are just hoping not to be voted off the island. Welcome to Strategy’s preferred stock lineup, where Stretch, Stride, Strike, and Strife are all vying for your love. Or your money. Or both. 😉

On July 21, 2025, Strategy casually dropped another preferred stock — this one, aptly named Stretch. Less than two months after launching its sibling, Stride, because apparently, Strategy believes in keeping things hot and happening. And just to keep us all on our toes, they’ve also tossed in Strike and Strife for good measure. It’s like the stock market’s version of ‘Pie, Pie, Pie!’

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Strategy's stock lineup

in a financial whoopsie, bondholders get paid first, preferred stockholders second, and the common folk (MSTR owners) last in line for the cash.

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Strategy’s preferred stocks
Stretch
Stride
Strike
Strife
MSTR common stock
Who gets paid first? The suspense!

Strategy’s Preferred Stocks: The Business of Bitcoin and Bonding

This delightful quartet—Stretch, Stride, Strike, and Strife—are all about Strategy’s grand Bitcoin ambitions, with a target of amassing $84 billion faster than you can say “HODL.” Think of these stocks as the company’s way of saying, “Hey, look at us, we’re innovative—and slightly reckless!”

These preferreds are not just about pretty dividends; they’re about sharing the pie with those brave enough to buy into Strategy’s crypto rollercoaster. No voting rights, but you do get a shot at the company’s caps and giggles (and profits). And, importantly, if Strategy goes belly-up, the preferred stockholders get paid before the common stockholders—who are just sitting there hoping for a miracle.

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The Bitcoin Defense Department — Michael Saylor (@saylor) July 23, 2025

But beware—the more preferred stocks Strategy issues, the more it has to fork out in dividends. And with Bitcoin’s infamous rollercoaster ride, that’s easier said than done. Critics whisper that this is riskier than trying to find a matching sock in your laundry.

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STRC is a USD pegged security backed by BTC… kinda like when Anchor promised 20% yields on Terra Luna. Hold onto your hats!

— Pledditor (@Pledditor) July 22, 2025

Stretch: The New Kid on the Block

Initially, Strategy threw $500 million into Stretch (STRC) on July 21 — because why not throw more cash into the carnival? By July 25, total offerings skyrocketed to $2.5 billion. They proudly announced they bought 21,021 Bitcoin for a cool $2.46 billion — because buying more Bitcoin is apparently the answer to all problems.

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Strategy’s Bitcoin Purchase

This new preferred stock offers a modest 9% annually, paid monthly—because patience is overrated when you have dividends on tap. The stock price is kept around $100, with the company able to always issue more — because what’s more fun than diluting your own assets? The call option feature makes it even more spicy.

Stride: The Ever-Perpetual

Debuting in June, Stride (STRD) is the perennial who refuses to call it quits, offering a steady 10% dividend paid quarterly. Unlike Stretch, it’s noncallable—so no buyouts here. Yet, the drama continues: some say Strategy might be forced to sell Bitcoin to keep the dividend fountains flowing, giving rise to whispers of Ponzi vibes. Yummy!

Strike: The OG Preferred

Back in January, Strike (STRK) made its debut with an 8% payout, and it’s got the bonus feature of convertibility into MSTR shares at a 10:1 ratio—like a secret handshake for investors who like options.

Strife: The High Roller

March brought Strife (STRF), with its 10% quarterly dividends. But here’s the kicker—there’s no ATM program for these shares, so Strategy can’t just keep issuing more. Instead, dividend payouts could escalate up to 18% if they get their act together. Fancy!

The Grand Line of Who Gets Paid First

If Strategy hits a rough patch—think of a Bitcoin storm—the money first goes to bondholders (like the VIPs). Next in line are preferred stockholders: Strife, then Stretch, then Strike, then Stride. And last but certainly not least, the humble MSTR shareholders, clinging to their shares like a lifebuoy in a sea of crypto chaos.

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Oversimplified. But if MSTR doesn’t act when the crypto gets stormy, things might get messy.

— Ki Young Ju (@ki_young_ju) December 17, 2024

While Strategy flexes its financial muscles, the crypto rollercoaster means everyone should keep their seat belts fastened. Because one day, Bitcoin and stocks might just have a very awkward chat — and nobody wants to be the one left holding the bag.

2025-07-31 18:25