A prominent early Bitcoin investor—often referred to as a “Trump insider” in crypto circles—has significantly expanded his bearish exposure, now holding short positions worth nearly $400 million.

A prominent early Bitcoin investor—often referred to as a “Trump insider” in crypto circles—has significantly expanded his bearish exposure, now holding short positions worth nearly 0 million.

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Key Points

  • Bitcoin has climbed back to $108,300, marking a modest 0.49% gain over the last 24 hours following a sharp downturn on October 10.
  • A prominent early Bitcoin investor—often referred to as a “Trump insider” in crypto circles—has significantly expanded his bearish exposure, now holding short positions worth nearly $400 million.
  • His latest move includes a $234 million short on Hyperliquid with a liquidation threshold at $123,000, signaling deep skepticism about the sustainability of the current rally.
  • Market sentiment remains neutral, with the Fear & Greed Index at 50 and Bitcoin dominance near 60%, reflecting cautious investor behavior.
  • Institutional activity, including growing adoption of spot Bitcoin ETFs, hints at a more mature market structure that could temper volatility over time.

A Fragile Rebound Amid Lingering Doubts

Bitcoin’s price has edged back to $108,300, recovering slightly from the turbulence that gripped the market earlier this month. The 0.49% uptick over the past day appears reassuring on the surface, especially after the sharp correction that began on October 10. Yet this rebound lacks the momentum that typically accompanies a strong bull continuation. Traders remain divided, with some viewing the move as a healthy consolidation while others interpret it as a dead-cat bounce before another leg down.

What makes this recovery particularly delicate is the backdrop of macro uncertainty and aggressive positioning by seasoned market operators. Unlike retail-driven rallies of the past, today’s price action unfolds in an environment shaped by institutional flows, regulatory scrutiny, and increasingly sophisticated derivatives strategies. This complexity adds layers of unpredictability, making it harder to gauge whether the current level represents a floor or merely a temporary plateau.


The Whale’s Calculated Gamble

One of the most notable developments in recent days comes not from a new entrant but from a veteran of the space—a Bitcoin OG whose reputation was cemented during the 2018 tariff-driven crash, where he reportedly netted $200 million by shorting the asset. This individual, known for his political connections and market timing, has once again taken a bold stance against BTC’s near-term prospects. His short exposure now totals approximately 3,440 BTC, valued at around $392 million, spread across multiple instruments and venues.

His most recent maneuver involved placing a $234 million short on the decentralized exchange Hyperliquid, with a liquidation price set at $123,000. Just one day prior, he had deposited 200 BTC—worth roughly $22 million—to bolster an existing short. Earlier in the week, he moved $30 million in USDC to open a $76 million position as Bitcoin flirted with recovery. These sequential, layered trades suggest a deliberate strategy rather than a speculative impulse. The whale appears to be betting that the current price level is unsustainable and that a retest of $100,000—or lower—is imminent.


Market Sentiment: Cautious Equilibrium

The broader market remains in a state of watchful neutrality. The Fear & Greed Index sits precisely at 50, a rare midpoint that reflects neither euphoria nor panic. Bitcoin dominance hovers around 60%, indicating that capital continues to favor the flagship cryptocurrency over altcoins—a typical behavior during uncertain phases. This preference for BTC often signals risk-off sentiment, where investors seek relative safety within the crypto ecosystem rather than chasing high-beta alternatives.

At the same time, institutional participation has grown more pronounced. The success of spot Bitcoin ETFs, particularly those backed by major asset managers, has introduced a new layer of structural demand. These products attract long-term holders and reduce the pool of liquid supply, potentially dampening extreme price swings over time. However, this maturation does not eliminate volatility entirely; it merely reshapes its expression. Short-term traders still face sharp moves driven by leverage, macro headlines, and large player activity—such as the whale’s recent short cascade.


Historical Patterns and Future Trajectories

Historically, Bitcoin has exhibited distinct price behaviors following halving events, often characterized by extended accumulation phases followed by explosive rallies. The current cycle appears to deviate slightly from past templates, with less dramatic drawdowns and a more gradual ascent. Long-term holder behavior supports this narrative: on-chain data shows minimal selling pressure from addresses that have held BTC for over a year, suggesting strong conviction among core participants.

Yet the presence of massive short positions—especially those held by individuals with proven track records—introduces a counterforce that cannot be ignored. If Bitcoin surges past $123,000, the whale’s Hyperliquid position could trigger a cascade of forced liquidations, potentially fueling a short squeeze. Conversely, if price stalls or reverses, his bearish thesis gains credibility, possibly encouraging others to follow suit. This dynamic creates a high-stakes equilibrium where market direction hinges on a narrow band of price action.


Conclusion

Bitcoin’s journey back above $108,000 offers a glimmer of stability, but the path forward remains fraught with tension. On one side, institutional adoption and long-term holder resilience point toward a more grounded, mature market. On the other, aggressive bearish bets by influential veterans underscore deep skepticism about the rally’s durability. The interplay between these forces—structural support versus tactical shorting—will likely define the next phase of price discovery. Traders should brace for volatility, not because the market is chaotic, but because it is increasingly contested by actors with divergent time horizons, strategies, and convictions.