Real estate investor Grant Cardone publicly challenged technology investor Jason Calacanis to a $1 million Bitcoin wager on October 28, 2026. Cardone offered to bet that Bitcoin will reach or exceed $126,210.50 by October 28, 2028, countering Calacanis’s declaration that the cryptocurrency would never reclaim its record high. The offer was public, but an accepted, funded bet has not been verified.

Cardone proposed settling the wager the moment Bitcoin reaches the specified price or when the two-year deadline expires, whichever comes first. He suggested that either side could rely on trust or both could place their funds with an independent escrow holder. A proposal for escrow is not evidence that money has been deposited.

Calacanis argues Bitcoin’s momentum has faded

The exchange followed a October 27 post from Calacanis, an early Uber investor and co-host of the All-In podcast. He forecast a possible return to $57,000, cited concerns about exchange-traded fund outflows and urged investors to favor artificial intelligence instead of Bitcoin. These are his forecasts and opinions, not established future outcomes.

The debate adds a personal wager to a wider market argument. Bitcoin has suffered a substantial drawdown from its October 2025 high, while investors weigh supply, interest rates, institutional demand and the value of its payments network. BitcoinVersus.Tech previously examined swings in Bitcoin ETF flows, which can vary sharply over short periods and do not guarantee a future price direction.

Three million-dollar challenges, but no confirmed settlement

Bitcoin investor Fred Krueger separately proposed a $1 million wager with a much longer 2036 deadline, while producer and Bitcoin educator Terence Michael also offered to participate. BitcoinVersus.Tech has previously covered Krueger’s bullish Bitcoin forecasts and the Bitcoin-versus-AI investment debate. The proposals use different deadlines and should not be treated as a single agreed contract.

Cardone’s broader Bitcoin position is not new: in an October 23 Yahoo Finance interview, he discussed combining Bitcoin exposure with income-producing real estate. Whether Calacanis ever accepts a wager, Cardone’s proposal puts an exact price, deadline and potential cash stake on a disagreement that otherwise remains hypothetical.

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