Tech investor and All-In podcast co-host Jason Calacanis has been presented with $3 million in proposed Bitcoin (BTC) bets after publicly claiming the cryptocurrency will never surpass its October 2025 peak of $126,210.50.
On October 27, Calacanis posted on X urging investors to sell Bitcoin and allocate capital into artificial intelligence (AI). Citing ongoing spot Bitcoin ETF outflows, he projected that Bitcoin will retest its $57,000 low within 12 months, calling the token a "dead network" that offers little utility outside of storing value.
The bearish forecast drew a response from Michael Saylor, executive chairman of Strategy (formerly MicroStrategy), who argued that AI and Bitcoin complement each other. Saylor stated that AI creates abundance while Bitcoin enforces scarcity.
$3 Million in Wagers Offered on X
Following the post, three prominent investors offered $1 million wagers challenging Calacanis to back his prediction against the $126,210.50 benchmark:
- Fred Krueger: Offered a $1 million bet on October 28, giving Calacanis a 10-year window until October 28, 2036, for BTC to break its record.
- Grant Cardone: Proposed a $1 million bet expiring on October 28, 2028, criticizing Krueger's timeline as too long.
- Terence Michael: Matched Cardone's terms with an additional $1 million offer expiring in October 2028.
- Adam Back: The Blockstream CEO and Hashcash creator signaled intent to join Cardone's side of the wager.
Calacanis countered Krueger by requesting a 12-month timeline matching his $57,000 retest forecast. However, he referred to Cardone's 2028 offer as "So much free money!" and asked for an escrow mechanism to finalize terms.
Smart Contract Proposed to Secure Escrow
To facilitate the terms, Krueger used AI to draft an Ethereum smart contract to escrow $1 million in USDC stablecoins from each party. The setup relies on Chainlink price oracles to verify whether Bitcoin touches $126,210.50 prior to the deadline, rewarding the full $2 million pool to the winner.
Despite the automated framework, Cardone stated that Calacanis has not yet formally accepted the wager, as the prototype contract awaits code testing and a security audit.
Why It Matters
High-profile public wagers serve as an informal barometer of market sentiment during prolonged price consolidation. By pinning predictions to precise price levels like $126,210.50 and verifiable deadlines, these challenges highlight the sharp debate between traditional tech investors rotating into AI and long-term crypto thesis advocates. If finalized, executing a $2 million escrow via an Ethereum smart contract would also showcase a practical decentralized application for resolving financial disputes without traditional intermediaries.
