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Dylan LeClair · Jun 29, 2026

Weekly Alpha: Saylor’s Strategy Remains Under Pressure

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We are now deep into a bear market. So let’s take a look at the latest price action and identify the key levels BTC may move to next.

What’s Happening


Latest Price Action

We are now deep into a bear market. So let’s take a look at the latest price action and identify the key levels BTC may move to next.

BTC continued to tumble this week, falling around -8% and sliding back below the 200-week moving average.

Figure 1: Bitcoin weekly performance

Live Price

That matters because the 200WMA has historically been one of Bitcoin’s most important long-term support levels, broadly identifying cycle-low regions throughout Bitcoin’s existence.

Figure 2: Bitcoin technical chart

For bullish price action to return, BTC needs to reclaim the 200WMA. If not, the next major downside level is Realized Price, currently around $53,200.

The 200DMA continues to drift lower and now sits at $75,600. Reclaiming that level will be the major confidence boost the market has been missing, but price is still some way from that level.

June is set to close deep in the red, with BTC down around -31% month-to-date, indicating we are now deep into bear market territory.

Figure 3: Monthly Returns Heatmap

Live Chart

Saylor’s Strategy Remains Under Pressure

Another major focus this week has been Michael Saylor’s Strategy.

Saylor posted again over the weekend, which has historically been his signal that another Bitcoin purchase disclosure may follow today. If confirmed, it would mark another week of buying, although the size of recent purchases has slowed sharply.

That is important because Strategy is now operating in a much more difficult environment. The company holds more than 847,000 BTC at an average cost of roughly $75,600, meaning its Bitcoin treasury is now materially underwater with BTC trading near $60,000.

Figure 4: Strategy Real-Time Treasury P&L

Live Chart

At the same time, Strategy’s premium to Bitcoin NAV has compressed heavily. Our data now shows mNAV around 0.73, meaning the market is valuing the company at a meaningful discount to the Bitcoin it holds.

Figure 5: Strategy Premium to Bitcoin NAV

Live Chart

This creates a clear tension. On one hand, Saylor continues to signal accumulation, and Strategy remains one of the most aggressive Bitcoin buyers in the market. On the other hand, a falling mNAV makes the funding model more difficult, especially if equity and preferred shares remain under pressure.

It is worth keeping the broader picture in mind though. Since adopting a Bitcoin standard, MSTR has still massively outperformed BTC and most major public market assets.

Figure 6: MSTR Performance Since Adoption

Live Chart

So while near-term pressure is real, the bigger question is whether Strategy can keep extending its runway without becoming a forced seller. For now, that seems to be the case but the market will be watching closely over the coming weeks.

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