Plus: At 100 years old, Caterpillar’s growth is now led by powering data centers.
Fortune 500 Digest with Alyson Shontell
Saturday, July 12, 2025
Foreword
Alyson Shontell
Editor-in-Chief

Good morning,

Sometimes, changing times demand changes in leadership. CEOs who excelled over the last decade may find they are not cut out for the AI era, which will require different skillsets, new org structures, and lots of nimbleness for incumbents that hope to thrive or even survive.

Top tech investor Vinod Khosla recently stated on Jack Altman’s Uncapped podcast that we are witnessing an unprecedented era of disruption—one that could take down a significant number of the world’s largest companies.

“One of my predictions is, the 2030s will see a faster rate of demise of Fortune 500 companies than we’ve ever seen,” Khosla said.

Which leaders will survive the disruption, and which should pass the baton? This week, Fortune’s Geoff Colvin dug into one of the biggest question marks, Apple’s Tim Cook. Since taking the reins from Steve Jobs in 2011, Cook has grown Apple’s revenue by more than $280 billion a year, and has increased its market cap more than 10x, to $3.2 trillion.

But Apple has been criticized for its sluggishness in AI, and its top AI executive was recently poached by Meta. Investors are getting restless: Its once-unbeatable stock is down more than 7% this year, while the Nasdaq is up 13%.

Is Tim Cooked? As Geoff writes, “In recent months, and especially in recent days, the impossible has become at least conceivable.”

Read Geoff’s story to learn more about the future of Apple’s leadership, and what could be in store.
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Catch Up
Fortune 500 C-suite Power Moves
Apple (No. 4) appointed Sabih Khan as COO, effective later this month. Baxter International (No. 288) appointed Andrew Hider as CEO, effective no later than Sept. 3. Unum Group (No. 330) appointed Andrew Walker as Chief Customer Operations Officer. Hershey (No. 379) appointed Kirk Tanner as CEO, effective Aug. 18. Toll Brothers (No. 390) appointed Gregg Ziegler as CFO, effective Oct. 31.
And more in this week's Fortune 500 Power Moves.
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Deals & Developments
  • Walgreens Boots Alliance (No. 26) shareholders have approved a takeover bid by Sycamore Partners valued at nearly $10 billion, the company announced. The take-private deal was initially announced in March and is expected to close between Q3 and Q4 of 2025.
  • Merck (No. 65) agreed to acquire Verona Pharma via a subsidiary for approximately $10 billion. Verona Pharma is a London, U.K.-based biopharmaceutical company developing therapies for respiratory diseases. Merck Chairman and CEO Robert M. Davis highlighted that the deal will bring Ohtuvayre, a novel COPD treatment approved by the FDA last year, under Merck’s umbrella.
  • US Foods Holding (No. 122) is reportedly considering acquiring Performance Food Group (No. 80), Bloomberg reported, which would create the largest wholesale food supplier in the country. In 2015, a federal judge blocked a deal in which Sysco (No. 56) would have acquired US Foods for $3.5 billion, due to competition concerns.
  • Kraft Heinz (No. 166) is considering branching off a large portion of its grocery business, per the Wall Street Journal, as demand has stagnated for some of the company’s more processed products. The new company would absorb a number of Kraft brands and could be worth nearly $20 billion. The company’s most popular offerings, like ketchup and other condiments, would remain under the original company.
Overheard
“Tesla isn’t riding on innovation right now, it’s riding on inertia.”
—Mark Pinsley, Lehigh County, Pa., Controller and a member of the Lehigh County Pension Board, which voted last May to halt any new investments in Tesla in the county’s actively managed funds.
On earnings calls:
  • Delta Air Lines (No. 70) CEO Ed Bastian noted that “overall demand for air travel remains similar to last year,” adding, “our core consumer is in good shape and continues to prioritize travel.” The company reported $15.5 billion in revenue for Q2, beating Wall Street’s expectations. Notably, the airline reinstated its full-year 2025 profit forecast, which it had pulled in April amid macroeconomic uncertainty. Delta Air Lines President Glen Hauenstein said on the call that “further-out bookings … [are] starting to return again.”
  • Conagra Brands (No. 350) missed Wall Street’s expectations with $2.78 billion in revenue for Q4, down from $2.91 billion in the same quarter last year and partially caused by a 4.3% drop in net sales. President and CEO Sean Connolly said in a statement that he expects “elevated inflation and macroeconomic uncertainty to persist” into the next fiscal year but will prioritize “investing in our high-potential frozen and snacks domains … and further enhancing supply chain resiliency,” among other efforts, to combat that uncertainty.
Earnings to watch next week include: JPMorgan Chase (No. 11), Citigroup (No. 21), Wells Fargo (No. 33), and Bank of New York (BNY) (No. 113) on July 15; Bank of America (No. 17), Goldman Sachs (No. 32), Morgan Stanley (No. 40), Johnson & Johnson (No. 48), and Prologis (No. 465) on July 16; PepsiCo (No. 45), U.S. Bancorp (No. 105), and Netflix (No. 116) on July 17; Truist (No. 168) on July 18; and other Fortune 500 companies.
Looking Ahead

July