Bitcoin

Bitcoin’s slide from its record high has split some of its loudest backers and critics into two camps. One side says the rally is over.&nbsp;
The other is now offering to put serious money behind the opposite view.
<a href="https://www.thestreet.com/crypto/real-estate" rel="noopener noreferrer nofollow">Real estate</a> investor <a href="https://www.thestreet.com/crypto/tag/grant-cardone" rel="noopener noreferrer nofollow">Grant Cardone</a> has challenged Jason Calacanis, an early <a href="https://www.thestreet.com/crypto/tag/uber" rel="noopener noreferrer nofollow">Uber</a> investor and co-host of the All-In podcast, to a $1 million wager on whether Bitcoin can return to its peak.
<a href="https://www.thestreet.com/crypto/bitcoin" rel="noopener noreferrer nofollow">Bitcoin</a> hit an all-time high of $126,080 on Oct. 6, 2025. At the time of writing, it was trading near $80,847, about 36% below that mark.
<figure><a href="https://app.decibel.trade/trade/BTC-USD" rel="noopener noreferrer nofollow"></a>
 <figcaption>
 Bitcoin price at press time on October 28. Source: <a href="https://app.decibel.trade/trade/BTC-USD" rel="noopener noreferrer nofollow">Decibel</a>
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<a href="https://www.thestreet.com/crypto/markets/top-analyst-calls-nasdaq-ai-firm-datavault-bitcoin-filing-one-of-the-ugliest-ever" rel="noopener noreferrer nofollow">Related: Top analyst calls Nasdaq AI firm's Bitcoin filing 'one of the ugliest' ever</a>
<h2 id="calacanis-calls-time-on-the-rally">Calacanis calls time on the rally</h2>
On Oct. 27, Calacanis told his followers on X that “a brutal year for Bitcoin is just getting started” and urged them to “dump it now.”
He pointed to money flowing out of Bitcoin exchange-traded funds, or ETFs, which let investors buy Bitcoin exposure through a regular brokerage account.
He predicted Bitcoin would “<a href="https://x.com/Jason/status/2114956980674605075" rel="noopener noreferrer nofollow">test the 57k low again in the next 12 months.”</a>
Calacanis called Bitcoin “a dead network that offers nothing beyond a store of value.”&nbsp;
A store of value is an asset people hold to preserve wealth over time, a role gold has long played.&nbsp;
He urged investors to “shift from Bitcoin to Super Intelligence,” arguing AI offers “unlimited upside for humanity.”
<blockquote>
 He ended the post with the line Cardone later picked up: “Bitcoin will never break its all-time high again.”
</blockquote>
<h2 id="cardone-puts-1-million-on-the-table">Cardone puts $1 million on the table</h2>
“Jason, I’ll bet you $1,000,000 it will break its ATH,” Cardone wrote on X. ATH is short for all-time high.
His terms set a target of $126,210.50, slightly above the record. The deadline is noon Pacific time on Oct. 28, 2028.&nbsp;
The wager would settle either when Bitcoin reaches that price or when the deadline passes.
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Cardone said he was “happy to trust” Calacanis to pay. He also offered to have both men deposit the money with an independent party, an arrangement known as escrow.
<blockquote>
 “Do we have a bet?” he asked.
</blockquote>
<blockquote class="twitter-tweet">
 Bitcoin will never break its all-time high again." — Jason Calacanis Jason, I'll bet you $1,000,000 it will break its ATH. Here are the terms: Bitcoin hits or exceeds $126,210.50 on or before October 28, 2028, 12PM PST I’m happy to trust you to pay or if you prefer we can…— Grant Cardone (@GrantCardone) <a href="https://x.com/GrantCardone/status/2115418568456118750?ref_src=twsrc%5Etfw" rel="noopener noreferrer nofollow">October 28, 2026</a>
</blockquote>
Cardone isn’t the only one taking the other side.
Investor Fred Krueger has also offered Calacanis a $1 million bet that Bitcoin will top its October 2025 peak before Oct. 28, 2036. Hollywood producer turned Bitcoin educator Terence Michael added another $1 million offer.
So far, Calacanis hasn’t accepted any of them.
<h2 id="a-10-year-view-from-wall-street">A 10-year view from Wall Street</h2>
Some institutional investors lean toward Cardone’s side, though over a much longer stretch.
Bitwise, an asset manager that runs crypto investment funds, published its <a href="https://s3.us-east-1.amazonaws.com/static.bitwiseinvestments.com/Research/Bitwise-Bitcoin-Long-Term-Capital-Market-Assumptions-2027.pdf" rel="noopener noreferrer nofollow">long-term Bitcoin outlook</a> in October.&nbsp;
Its base case puts Bitcoin at about $1.6 million by 2036, which works out to an average annual return of 34.3%.&nbsp;
Its bull case reaches $3.67 million. Even its bear case, at $130,686, sits above today’s record.
<blockquote>
 Bitwise expects Bitcoin to be “the best-performing major asset in the world over the next decade.”&nbsp;
</blockquote>
For comparison, it projects annual returns of 6.7% for <a href="https://www.thestreet.com/crypto/tag/us-stock-market" rel="noopener noreferrer nofollow">U.S. stocks</a> and 5.5% for gold over the same period.
The firm also flags risks.&nbsp;
It calls the figures illustrative rather than predictions and names “technological disruption” among the biggest long-term threats to its forecast.
Cardone’s own optimism goes back further.&nbsp;
In September, he <a href="https://x.com/GrantCardone/status/2094516491333038427" rel="noopener noreferrer nofollow">told followers</a> that Bitcoin would become an everyday means of payment once its total market value reaches $20 trillion.
<blockquote class="twitter-tweet">
 BTC will become as a means of exchange when its market cap hits $20T. 🔖 Bookmark this— Grant Cardone (@GrantCardone) <a href="https://x.com/GrantCardone/status/2094516491333038427?ref_src=twsrc%5Etfw" rel="noopener noreferrer nofollow">August 31, 2026</a>
</blockquote>
For now, the two investors are two years and roughly $45,360 per coin apart.
<h2 id="the-roundtable-100">The Roundtable 100</h2>
If you follow our market coverage, don’t miss the <a href="https://roundtable100.com/tab/rankings" rel="noopener noreferrer nofollow">Roundtable 100</a>. Updated every Friday, it's a power ranking of the 100 most investable tech stocks, including digital assets. Check out the latest <a href="https://roundtable100.com/" rel="noopener noreferrer nofollow">RTB 100</a> rankings at <a rel="noopener noreferrer nofollow">roundtable100.com</a>
<a href="https://www.thestreet.com/crypto/markets/wall-street-giants-worth-17-trillion-reject-new-trading-plan" rel="noopener noreferrer nofollow">Related: Wall Street giants worth $17 trillion reject new trading plan</a>

Grant Cardone challenges Bitcoin bear to $1 million bet

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