Newsletter · 2026-10-05 · Ashutosh Agarwal

Jim Chanos Beat Michael Saylor and Carvana Is Still Out on Bail - Track Record - June 2025 to October 2026

A historical scorecard of short-seller Jim Chanos, who put a long bitcoin / short Strategy (MSTR) pair trade and a Carvana (CVNA) short on the record on Bloomberg Talks on June 11, 2025, with performance measured through the October 2, 2026 close. The Strategy pair was unwound around November 7, 2025 with MSTR down 37.5% against bitcoin's 4.8% dip; Carvana is down 6.3% against the S&P 500's 28.2% gain but has not collapsed. Verdict: Right on the pair, Right vs. market but Too Early on the Carvana collapse.

Track Record

Jim Chanos, June 2025 to October 2026

This is a historical review of Jim Chanos's two shorts from his June 11, 2025 Bloomberg Talks interview, a long bitcoin / short Strategy (MSTR) pair trade (first pitched to clients on December 5, 2024) and a Carvana (CVNA) short, with performance measured through the October 2, 2026 close. It was published on October 5, 2026; the prices and grades below are as of the October 2, 2026 cutoff.

This issue covers short-seller Jim Chanos. His bitcoin-vs-Strategy pair trade was a clean win. His Carvana short is working against the market, but the stock hasn't collapsed.

Jim Chanos made his name in 2001 by spotting Enron before it blew up. These days he runs Chanos & Company, a family office and advisory firm. He no longer manages outside money, but he still publishes short ideas to clients.

His approach matters for how we grade him. In his own words on RiskReversal Pod, he says: "we're not directional". He runs a short book that is hedged against long positions in the stock indices. So the fair question for a Chanos short is not "did the stock go down?" The question is "did it do worse than the market?"

On June 11, 2025, Chanos sat down with Scarlet Fu on Bloomberg Talks and put two shorts on the record in a single interview:

• Strategy (MSTR), Michael Saylor's bitcoin-buying company, structured as a pair trade (long bitcoin, short MSTR)
• Carvana (CVNA), the online used-car seller

Sixteen months later, we can grade both.

The Call

Call #1: Long bitcoin, short Strategy (MSTR)

Where: Bloomberg Talks: "Chanos & Company President Jim Chanos Talks Bull Market, Carvana and Michael Saylor" (June 11, 2025), with host Scarlet Fu.

The setup. Strategy (formerly MicroStrategy) raises money by selling stock and bonds and uses it to buy bitcoin. For most of 2024–25, the stock traded far above the value of the bitcoin the company owned.

The ratio of the company's market value to its bitcoin holdings is called "mNAV" (multiple of net asset value). At 2.0x, investors pay $2 of stock for every $1 of bitcoin the company holds.

Chanos's trade: buy bitcoin and short MSTR stock. That is a bet that the premium shrinks, whatever bitcoin itself does. He was clear he had no view on bitcoin:

"Let's be clear. It's a hedge trade. I don't know where Bitcoin is going to go... The premium compressing matters to me."

The prediction, in his words:

• Entry level: "we put this trade on and advise clients somewhere between 2.2 and 2.3." On the day of the interview, he put the premium at "about 1.8."
• Target: Asked where the premium should be, he said: "It should be at one."
• Catalyst: "The catalyst is Michael Saylor... he's been selling equity to himself." He also pointed to copycats: "There's nothing proprietary about Michael Saylor's business model... the more and more supply we're going to see, the less and less premium anybody's going to have."
• Exit rule: Saylor had said the day before (Bloomberg Talks, June 10, 2025) that the company would buy back stock if it ever traded below 1x. Chanos's reply was "I can assure you if it trades below 1, I will have covered my short."
• Timeframe: None given. It was framed as an arbitrage that would close when the premium collapsed.

When it actually started. On a later podcast, The Investor's Podcast Network: "BTC243: Jim Chanos Vs Pierre Rochard MSTR mNAV debate" (July 16, 2025), Chanos said the idea went to clients earlier: "I gave this as an idea at my annual investment conference on December 5th. I think the mNAV was about 2.5 at that point." He also said the position was sized at "less than 5% of our portfolio."

Call #2: Short Carvana (CVNA)

Where: Same episode. Bloomberg Talks (June 11, 2025).

Scarlet Fu called it "a new short idea." Chanos called it a re-short: "We were short the stock successfully in 2022 and 2023 and covered, and now it's back."

The thesis, in three parts:

1. The accounting. "About 70% of their operating profit is coming from gain on sale of subprime loans." Carvana lends to car buyers with weaker credit, then sells those loans and books the profit. Chanos thinks that kind of profit doesn't deserve a growth-stock price: "you should not be putting an enormous multiple on this 50, 60, 70 times."
2. The history. Carvana's chairman, Ernie Garcia II, previously ran Ugly Duckling, a 1990s subprime car lender that "got into trouble for subprime lending" and later became DriveTime, Carvana's former parent.
3. The timing signals. "The short interest has collapsed", meaning the other bears had given up. And "we've seen a dramatic increase in insider selling... in May and June."

His line on the stock's run: "Investors on the long side look for that 100 bagger. We do too for companies that are already up 100x."

The prediction: CVNA would fall, particularly if the market for subprime auto loans cooled. He gave no price target and no timeframe.

On Odd Lots: "Jim Chanos on the Nuttiness of 'Bitcoin Treasury Companies'" (June 30, 2025), with Joe Weisenthal and Tracy Alloway, he went further. He said Carvana was making "more than 100% of their pre-tax profit from gain on sale of loans, subprime loans, and gain on sale of equity stakes in other companies. And you X those two out, they're losing money."

What Happened

All prices are daily closes. Bitcoin is tracked with BlackRock's iShares Bitcoin Trust (IBIT), a fund that holds bitcoin. Returns run to the October 2, 2026 close. mNAV levels are as stated by Chanos.

Strategy vs. bitcoin

In plain English: bitcoin barely moved between the June 2025 podcast and the November 2025 exit. MSTR stock lost more than a third of its value. Almost all of that drop came from the premium collapsing, which is exactly the mechanism Chanos bet on.

By his own count, the premium went from 2.2–2.5x when he started, to about 1.8x at the podcast, to about 1.2x when he closed the trade.

The painful stretch. It did not go in a straight line. Five weeks after the podcast, MSTR hit its high for the period, $455.90 on July 16, 2025. That was up 17.8% from the call date, while bitcoin was up 9.7%. At that point the pair was 8 points underwater.

After that, MSTR fell steadily. It bottomed at $82.31 on June 26, 2026, well after Chanos had exited.

Carvana

A note on prices: Carvana did a 5-for-1 stock split effective May 8, 2026. The figures below are split-adjusted, with the pre-split equivalent in brackets. That way they match the ~$330–400 prices Chanos quoted on podcasts.

In plain English: a straight short of Carvana from June 2025 has made about 6%, which is modest. Chanos runs shorts against long index positions, though. On that basis, Carvana trailed the S&P 500 by about 34 points, which is a big win.

But the investor who held on had a rough ride. By January 2026 the stock was up 40% and the hedged position was more than 25 points underwater. It swung sharply along the way, including a 17% one-day move on July 31, 2025 and a 14% one-day move on January 28, 2026.

The Verdict

Strategy / bitcoin pair: Right

This was close to a textbook short-seller call: specific mechanism, specific entry, specific target, specific exit rule, and a confirmed exit.

What he got right:

• The mechanism. He said the premium was the trade, not bitcoin. Between the podcast and his exit, bitcoin fell less than 5% and MSTR fell 37.5%.
• The catalyst. He said Saylor's own stock sales and a wave of copycats would drain the premium. By October 2025, Chanos noted that most of the "strategy wannabe companies" had "gone to below 1.0 NAV."
• The discipline. He took the trade off at about 1.2x, before his stated 1.0x target. He did not stay in out of stubbornness.

The uncomfortable parts:

• He didn't hit his own target. He said the premium "should be at one." He exited around 1.2x, and by May 2026 he put it at "about 1.3 now." The premium shrank, but it never fully closed.
• The trade did not hold up as a pure arbitrage. MSTR uses borrowed money and preferred stock, so it tends to fall more than bitcoin when bitcoin falls. After Chanos exited, the stock-level spread widened another 15 points, even though the premium itself barely moved. Some of the post-exit "gain" came from that leverage, not from the premium closing.
• It hurt before it worked. Anyone who copied the trade on June 11, 2025 was down about 8 points within five weeks, as MSTR ran to $455.90.

None of that changes the grade. He named the trade, the reason, and the exit, and all three played out.

Carvana short: Right relative to the market; the collapse he predicted is Too Early

What he got right:

• Against the market, this short has been a clear winner: CVNA -6.3% versus S&P 500 +28.2%.
• His timing indicators were reasonable. Collapsed short interest and heavy insider selling were the setup he cited. The stock has gone nowhere since.

What he got wrong, or hasn't been proven right on yet:

• The stock hasn't broken. Chanos's core story was that Carvana's profits depend on selling subprime loans, and that this would end badly if credit markets tightened. That hasn't happened. Carvana is still trading roughly where it was 16 months ago.
• The drawdown was severe. At the January 2026 peak, the stock was up 40% from his call. For a short seller, that is the period when clients start questioning the idea.
• A straight short made only about 6%. An investor who shorted Carvana without a hedge would have made a small gain for 16 months of risk on a stock that moved 10–17% in a day more than once.

Have They Changed Their Tune?

On Strategy: he took the win and said so

• Bloomberg Talks: "Jim Chanos Talks Credit Markets, Bitcoin" (October 22, 2025), with Scarlet Fu. Mid-trade update: "since we were on last... the so-called MNAV, the premium, has compressed from about 1.9 to 1.4." Was he out? "We have not covered any of our shorts. But, you know, again, we reserve the right to change our mind." He said he never shorted the copycats: "No, we did not. We just kept it to strategy." He also described the size of the gap: "The premium at 2 plus was at one point, I think, $50 or $60 billion, just the premium." MSTR was at $280.81 that day and fell another 13.8% by the time he exited.
• The exit (~November 7, 2025). On MSTR Today: "Jim Chanos wins. What does this mean for Michael Saylor?" (November 9, 2025), the host read Chanos's public post: "I can confirm that we have unwound our MSTR Bitcoin hedge trade as of yesterday's open." This is the host reading the post, not Chanos speaking.
• RiskReversal Pod: "Jim Chanos: The Bears Are Out Of Hibernation" (February 6, 2026), with Dan Nathan and Guy Adami. Looking back: "we called it our big short of 2025, because it's just rare that you get a convergence of all of those factors, silly structure, doable with incredible amounts of liquidity and a catalyst by the companies themselves helping you."
• Closing Bell: "Live From the Sohn Conference 5/12/26" (May 12, 2026), with Scott Wapner. Asked why he got out: "the MNAV collapsed. So we were doing it between 2 and 2.5, and in November it got down to about 1.2 and we took the trade off." He added that "it was an $80 billion discrepancy at one point, which is rare in these kinds of trades... This one you literally could do in billions of dollars."

On Carvana: he doubled down, and that has worked so far

• Bloomberg Talks (October 22, 2025): "We're still short Carvana." On subprime lending trouble elsewhere in the industry: "the fact that Carvana seems to be sailing through it with nary a scratch stretches credulity." He also flagged that a Carvana affiliate, BridgeCrest, services the loans. CVNA was $65.38 (~$327 pre-split) that day. Since then it is -2.5% versus the S&P 500's +15.3%.
• RiskReversal Pod (February 6, 2026): He admitted the short had moved against him: "we put the name out again this summer, I think at the three 30 or something like that... So it's still above that." He then sharpened the case: "94% of their pre-tax profits comes from gain on sale of... loans, particularly subprime loans." And: "What would Carvana make if all their customers walked in and paid cash for the cars? The answer is they would make virtually no money." When Dan Nathan asked why it wasn't one of the best shorts ever, Chanos replied, "I don't know why it's not a great short. We think it is." CVNA was $80.73 (~$404 pre-split) that day. Since then it has fallen 21.0% while the S&P 500 rose 11.4%, so doubling down at that point paid off.

Running Scorecard: Jim Chanos

Chanos so far: 2 calls graded. Both beat the market on a hedged basis. One has fully played out (the Strategy pair) and one is still open (Carvana).