Two legendary investors. One stock. Completely opposite positions. And one of them is sitting on a paper gain of roughly $2.27 billion.
Back on July 1, I reported when Michael Burry shorted Caterpillar for the first time in his career on June 30, writing in his Cassandra Unchained newsletter:
I have never shorted Caterpillar. Today I shorted Caterpillar. It has always done great for me on the long side in the past.
He entered at $1,060.98. Caterpillar (CAT) has since pulled back to $827.90 as of August 21, according to Yahoo Finance. It is down more than 20% from where he initiated the short. By that math, the man who called the 2008 housing crash is currently winning this particular trade.
But here is the thing about the other side of that bet. The Gates Foundation Trust held approximately 6.35 million Caterpillar shares, valued at $6.77 billion as of June 30, 2026, compared with approximately $4.50 billion as of March 31, according to the trust’s Q2 13F filing.
That is a roughly $2.27 billion increase in the reported position value in a single quarter.
Even after the drop from the all-time intraday high of $1,073.46 on June 29, 2026, CAT has still returned 100% over the past year, as of this reporting, according to Yahoo Finance. Guru Focus data shows that it is Gates’s second-largest holding at 19.65% of the portfolio.
That is exactly what a patient, concentrated long position looks like when the cycle turns in your favor.
Also Read: History of Caterpillar: Company timeline & facts
How the Gates Foundation Trust thinks about Caterpillar
I have covered two Gates Foundation trust moves recently.
- The $818 million trim of Berkshire Hathaway, which led to the new $352 million Home Depot position
- The new $180 million FedEx Freight stake.
Each one tells you something about how this portfolio is managed. The new positions rotated toward companies that benefit from domestic economic activity and physical asset maintenance rather than purely financial holdings.
The top five holdings, according to GuruFocus, are Berkshire Hathaway Class B at 21.35%, Caterpillar at 19.65%, Canadian National Railway at 17.95%, Waste Management at 17.30%, and Deere & Company at 6.56%.
More Caterpillar:
- Caterpillar buys little-known AI startup in surprise tech move
- Cathie Wood buys another $72 million of mega-cap tech stock
- BofA sees more power behind Caterpillar shares
The portfolio is essentially a bet on the physical infrastructure of North American and global commerce — railroads, waste, construction equipment, heavy machinery.
Caterpillar fits that theme perfectly too. It is the world’s leading manufacturer of construction and mining equipment, off-highway engines, industrial gas turbines, and diesel-electric locomotives. It sells to the companies building roads, mines, power plants, and data centers.
Related: Caterpillar tariffs send major signal on margins
The Artificial Intelligence (AI) infrastructure boom has been its unexpected tailwind, with data center construction driving demand for the same earthmoving equipment that historically followed commodity and housing cycles.
Caterpillar’s second quarter 2026 results confirmed the scale of what is happening. Caterpillar reported sales and revenues of $20.5 billion in Q2, a 24% year-over-year increase. In fact, it is the first time in the company’s history that it has generated over $20 billion in a single quarter, according to CEO Joe Creed’s statement in the earnings release.
Adjusted profit per share was $8.17. The company deployed $2.2 billion in share repurchases and dividends in the quarter.
“Strong order rates and a growing backlog reflect broadening momentum across all three of our primary segments,” Creed said.
Burry’s case against CAT, and what has happened since
Burry’s CAT short argument was macro and structural: the AI infrastructure spending surge and the valuations it generated across semiconductors and industrials alike were closer to a peak than the market believed.
On that specific trade, the price action has moved in his direction. As mentioned, CAT hit an all-time intraday high of $1,073.46 on June 29, 2026, a day before Burry’s short disclosure at $1,060.98. It has since fallen to $827.90. At that magnitude, Burry’s short has worked.
Related: Michael Burry makes first-ever bet against longtime favorite stock
What is interesting is that Burry described CAT as a stock that had “always done great for me on the long side.” This is not a bear case built on a broken business.
It is a tactical short against a stock that ran more than 100% in a year on the back of a spending cycle that Burry believes is more fragile than the market is pricing.
What the $2.27 billion gain tells long-term investors
To be precise, the $2.27 billion increase in Gates’s reported CAT position value through June 30 is an unrealized gain, not a realized profit. The 13F filing covers what was held at quarter-end, not what has happened since.
CAT’s subsequent pullback would have reduced that number massively. Whether the trust has trimmed, held, or added to the position since June 30 will not be known until the Q3 filing. I want to believe that at least Gates trimmed it just like he did Berkshire.
Related: Bill Gates pulls $818M from Berkshire to buy this giant
But the directional story stands regardless. Patient, concentrated ownership of a world-class industrial business through a multi-year infrastructure demand cycle generated roughly $2.27 billion in value creation in a single quarter. According to Yahoo Finance, CAT’s 5-year return of 340.25% versus the S&P 500’s 72.78% is the long-term validation of the thesis.
Gates is sitting on years of compounding gains. Burry just made money on the short-term correction. The same stock. Completely different investment philosophies. Both investors, for now, are winning on their own terms.
Related: Bill Gates makes $180 million bet on backbone of America’s economy
