Scott Melker, known as The Wolf of All Streets, recently made waves by calling Michael Saylor “one of the worst traders in modern history.” But behind that bold statement lies a deeper insight into how market timing — even for billion-dollar Bitcoin buys — may be an illusion. So is this just sensationalism, or a serious critique?

Melker’s Claim: Harsh Words with a Twist

https://x.com/saylor/status/1909214598185500907

https://x.com/saylor/status/1899425381360288059

Breaking down why Melker called out Saylor’s market timing

Scott Melker’s comment wasn’t just clickbait. In his April 8 newsletter The Wolf Den, Melker laid out why Saylor’s Bitcoin purchases may look flawed through a short-term trader’s lens. According to Melker’s data, Strategy made roughly 20% of its BTC buys above $90,000 per coin. And while the firm holds over 528,000 BTC today, its average purchase price is $67,400 — just $10,000 below current market prices.

Melker highlights that in 2025 alone, Saylor only “bought the dip” in 3 out of 9 instances — and in one of those dips, the purchase was just 130 BTC, far below Strategy’s typical acquisition size. All of this contributes to the perception that Saylor isn’t a savvy trader, but a highly aggressive accumulator.

Beyond the Surface: The Long-Term Vision

Saylor isn’t trying to trade — he’s trying to dominate supply

Melker quickly pivots to explain that the real issue isn’t Saylor’s timing — it’s that market timing itself is a flawed concept. Saylor, who famously said “one Bitcoin equals one Bitcoin,” is playing a different game. His goal isn’t maximizing short-term profits, but acquiring the largest possible percentage of the total Bitcoin supply.

In his 2025 speech Bitcoin for America, Saylor compared buying Bitcoin to buying the United States — noting that 78% of U.S. land was once bought for just $40 million. His strategy views Bitcoin as generational infrastructure, not a trade.

He believes any price today is a discount compared to his long-term target: $13 million per BTC by 2045.

Traders vs. Accumulators

What’s the difference between investing and trading in Bitcoin?

Melker emphasizes that Saylor’s approach shouldn't be judged like a hedge fund’s. Instead of timing highs and lows, Saylor uses leverage and strategy to accumulate BTC over time, regardless of temporary volatility.

That said, Melker doesn’t let him off the hook entirely. He points out that while Saylor’s strategy is visionary, it's not without real-world risks. Strategy uses debt to buy Bitcoin — and if BTC ever crashed to around $16,000 without action, bankruptcy could become a risk. Still, that scenario seems distant given current market conditions.

Melker closes his analysis by stating: “There’s never been a better moment for companies to enter the Bitcoin arena... accumulating BTC near Saylor’s average is a rare gift from the market gods.”

The Joke Within the Insult

Why “worst trader” may be a tongue-in-cheek compliment

Melker's quip about Saylor being a bad trader is ultimately a rhetorical device. He’s making a broader point: trying to time Bitcoin is nearly impossible, and even the biggest whales misjudge the market. But that doesn’t mean they’re wrong.

Saylor’s strategy is unique. Instead of trying to predict price swings, he’s rewriting the narrative of treasury management by betting everything on Bitcoin as a national-level reserve asset. That boldness is what defines him — not whether he bought on the perfect dip.

And as Melker notes, if Saylor really wanted help timing markets, “he could call up Ray Dalio or Ken Griffin and have a team of quants running fresh models for him by dinner.”

Info Box 1: Saylor’s Bitcoin Stats

• Total BTC held: Over 528,000
• Average cost basis: $67,400
• Estimated value at $13M per BTC (2045 projection): Over $6.8 trillion
• BTC purchases above $90K: ~20%
• 2025 Dip Buys: Only 3 out of 9 events

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