Three investors offered Jason Calacanis $1 million each in Bitcoin bets after his 'dead network' post. He has not accepted, and Adam Back is interested.
Three investors have each put a $1 million Bitcoin bet to Jason Calacanis. The All-In podcast co-host had previously said that BTC would not surpass its all-time high again.
Adam Back, CEO of Blockstream, has also indicated interest in joining. Calacanis labeled one proposal as free money and raised the question of escrow, yet he has not officially agreed. This standoff occurs while Bitcoin remains far beneath its October 2025 high.
The X post that sparked the betting offers was published on October 27. In that message, Calacanis told investors to sell Bitcoin and shift their money into AI. He pointed to outflows from spot Bitcoin ETFs and predicted a revisit of $57,000 within 12 months.
A brutal year for Bitcoin is just getting started.
— @jason (@Jason) October 27, 2026
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.
Why?
Because there are far too many dynamic places to… pic.twitter.com/fK8zRNvPU0
The angel investor also referred to Bitcoin as a “dead network” with little value beyond storing wealth.
Michael Saylor, executive chairman of Strategy (the company previously known as MicroStrategy), responded quickly to Calacanis's Bitcoin crash call. Saylor, who had recently attributed Bitcoin's difficulties to AI spending, said the two fields work together.
“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
Each of the four investors is betting on the same result. They take the money if Bitcoin exceeds $126,210.50, the set reference point for its October 2025 high, by their respective deadline. If not, Calacanis wins.
Fred Krueger, a Bitcoin investor, submitted the earliest and most extended proposal, allowing Calacanis to wait until October 28, 2036.
"Bitcoin will never break its all-time high again."
— Fred Krueger (@dotkrueger) October 28, 2026
— Jason Calacanis
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…
Calacanis responded by requesting a 12-month wager instead. That timeframe aligns with his $57,000 prediction, not with his assertion that Bitcoin will never reach a new high.
Grant Cardone, who invests in real estate, set a tighter deadline of October 28, 2028. Cardone also took issue with Krueger's 10-year span, saying a serious offer should anticipate a record high within 12 to 18 months.
Terence Michael, a Bitcoin educator, later backed Cardone's terms with an additional $1 million. Adam Back, known for his Hashcash contribution referenced in the Bitcoin white paper, proposed adding funds to Cardone's position.
The reaction to Cardone's offer differed. Calacanis described it as “So much free money!” and subsequently noted that it is difficult to ignore free money.
So much free money! https://t.co/tQyTDDJNPo
— @jason (@Jason) October 28, 2026
Calacanis also requested from Cardone an escrow arrangement or a platform to secure the wager.
Krueger subsequently urged both parties to commit, using a structure that avoids lawyers and escrow agents. He employed AI to write an Ethereum smart contract for the specific bet between Cardone and Calacanis.
In this arrangement, each party would put up $1 million in the USDC stablecoin. Chainlink's oracle would confirm Bitcoin's price, with the victor receiving the entire $2 million.
Krueger acknowledged that the prototype requires further testing and a security review. As of now, Cardone says Calacanis hasn't agreed to the wager.
Should the Bitcoin bet proceed, the timeline will determine the outcome. Historical cycle patterns indicate BTC might regain its peak by mid-2027, falling within Cardone's 2028 deadline. Prolonged ETF outflows could disrupt that trend, though.
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Disclaimer: this article comes from third-party media and is provided for reference only. It does not constitute investment advice. Crypto and other financial products carry significant price volatility risk, so please make your own decisions carefully.
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