Calacanis faces $3M Bitcoin bets after calling BTC a "dead network

The genesis of this situation was a post shared on X, which first appeared on BeInCrypto.

Calacanis, a co-host of the All-In podcast, asserted that Bitcoin would never achieve another all-time high, leading three separate investors to each propose a $1 million wager. Furthermore, Adam Back, the CEO of Blockstream, has also indicated his interest in participating. Although Calacanis has characterized one of the proposals as "free money" and inquired about escrow arrangements, he has not formally agreed to any of them. This disagreement surfaces while Bitcoin's current trading price remains significantly below its high point established in October 2025.

The post that sparked these betting offers surfaced on October 27. In that communication, Calacanis strongly encouraged investors to divest from Bitcoin and reallocate those funds into artificial intelligence (AI). He pointed to the observed outflows from spot Bitcoin Exchange-Traded Funds (ETFs) and predicted that the price would retest the $57,000 level within the subsequent year, suggesting that a harsh year for Bitcoin is merely beginning. He stated, "Give me three minutes to explain why you should dump it now. Outflows from ETFs are signal and will continue. We will test the 57k low again in the next 12 months." He questioned this outlook by asking, "Why? Because there are far too many dynamic places to…".

The investor also labeled Bitcoin a "dead network," suggesting it provides little more than a means of storing value. His bearish prediction regarding Bitcoin prompted a swift response from Michael Saylor, the executive chairman of Strategy at MicroStrategy. Saylor, who recently attributed Bitcoin's difficulties to spending in the AI sector, countered that the two fields actually support each other. He remarked, "AI creates abundance. Bitcoin enforces scarcity. One expands humanity’s ability to create value. The other lets us preserve and transfer it across time and space. Digital Intelligence and Digital Capital are complementary, Jason. The world needs both."

The various Bitcoin betting proposals test the longevity of Calacanis's "never" claim. All four challengers have placed their bets on the identical outcome: they win if BTC surpasses $126,210.50, which is the benchmark set by its October 2025 peak, before a specified date; otherwise, Calacanis profits.

Bitcoin investor Fred Krueger initiated the betting sequence with the longest commitment, setting a deadline of October 28, 2036, for Calacanis. Krueger challenged him, stating, "Bitcoin will never break its all-time high again." He followed up with, "Jason, I'll bet you $1,000,000 that you're wrong. Here are the terms: Bitcoin must exceed $126,210.50 (its October 2025 ATH) before October 28, 2036. If Bitcoin does, I win $1 million. If it doesn't, you…".

In response, Calacanis requested a shorter commitment period, specifically a 12-month bet, a timeframe that aligns more closely with his $57,000 forecast than his absolute claim about a new high. Real estate investor Grant Cardone proposed a more immediate deadline of October 28, 2028, and also critiqued Krueger's decade-long timeframe, arguing that a credible offer should anticipate a new high within 12 to 18 months. Terence Michael, a Bitcoin educator, subsequently matched Cardone's proposed terms with another $1 million stake. Adam Back, whose work on Hashcash is referenced in the Bitcoin white paper, volunteered to contribute additional funds to Cardone's side of the wager.

Cardone's offer elicited a different reaction from Calacanis; he remarked, "So much free money!" and later noted that such opportunities are difficult to pass up. Calacanis also asked Cardone about establishing an escrow service or platform to secure the bet. Krueger then urged both parties to commit, outlining a structure that bypasses the need for legal counsel or escrow agents. He arranged for an AI to generate an Ethereum smart contract covering solely the wager between Cardone and Calacanis. According to this arrangement, each participant would deposit $1 million in the stablecoin USDC; Chainlink’s price oracle would confirm Bitcoin's price, and the victorious party would claim the full $2 million. Krueger cautioned that the initial model still requires security auditing and further testing. To date, Cardone reports that Calacanis has not accepted the wager. Should the Bitcoin bet proceed, the final decision will hinge on the timeline chosen. Data from previous market cycles suggests Bitcoin could recover its record by the middle of 2027, falling within Cardone's 2028 window, though sustained ETF outflows could alter this trajectory.

Why it matters

This public betting action highlights the extreme divergence in market sentiment regarding Bitcoin's future price ceiling. The proposed smart contract mechanism shows how high-stakes predictions are being formalized in the crypto space. Readers should watch the timeline of these bets to gauge shifts in market conviction.