Three investors have each offered Jason Calacanis a $1 million Bitcoin bet. The All-In podcast co-host had claimed that BTC will never break its all-time high again.
Blockstream CEO Adam Back has also signaled he wants in. Calacanis has called one offer free money and asked about escrow, but has not formally accepted. The clash comes as Bitcoin still trades well below its October 2025 peak.
Why Calacanis Wants Holders to Sell Now
The post that triggered the Bitcoin bet offers came on October 27. In it, Calacanis urged investors to dump Bitcoin and rotate into artificial intelligence (AI). He cited outflows from spot Bitcoin ETFs and expects a retest of $57,000 within 12 months.
The angel investor also called Bitcoin a “dead network” that offers little beyond a store of value.
His Bitcoin crash call drew a fast response from Michael Saylor, executive chairman of Strategy, formerly MicroStrategy. Saylor, who recently blamed AI spending for Bitcoin’s struggles, argued that the two sectors complement each other.
“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.”
Michael Saylor, X
Bitcoin Bet Offers Test How Long “Never” Lasts
All four challengers bet on the same outcome. They win if BTC tops $126,210.50, the agreed benchmark for its October 2025 record, before their deadline. Otherwise, Calacanis collects.
Bitcoin investor Fred Krueger made the first and longest offer, giving Calacanis until October 28, 2036.
In reply, Calacanis asked for a 12-month bet instead. That window matches his $57,000 forecast rather than his claim that a new high will never come.
Real estate investor Grant Cardone set a shorter deadline of October 28, 2028. Cardone also criticized Krueger’s 10-year window, arguing that a credible offer would expect a new high within 12 to 18 months.
Bitcoin educator Terence Michael later matched Cardone’s terms with another $1 million. Back, whose Hashcash work is cited in the Bitcoin white paper, offered to add more money to Cardone’s side.
Cardone’s offer drew a different reaction. Calacanis called it “So much free money!” and later added that free money is hard not to pick up.
Calacanis also asked Cardone for an escrow or platform that could lock the bet in.
Krueger then pushed both sides to commit, with a setup that needs no lawyers or escrow agents. He had AI draft an Ethereum smart contract covering only the bet between Cardone and Calacanis.
Under the plan, each side would deposit $1 million in the stablecoin USDC. Chainlink’s price oracle would verify Bitcoin’s price, and the winner would take the full $2 million.
Krueger noted that the prototype still needs testing and a security audit. So far, Cardone says Calacanis has not accepted the bet.
If the Bitcoin bet goes ahead, the timeline will decide it. Past cycle data suggests Bitcoin could reclaim its record by mid-2027, inside Cardone’s 2028 window. Longer ETF outflows could break that pattern, however.
