Now that Warren Buffett has confirmed Greg Abel will take over as Berkshire Hathaway’s CEO by year-end, attention is turning to another major succession question: Who will step into Ajit Jain’s shoes?
For nearly 40 years, Jain has been the force behind Berkshire’s insurance operations. His knack for pricing complex risks has helped generate the massive cash flow that powered Buffett’s acquisitions and stock picks.
“Even kryptonite bounces off Ajit,” Buffett once wrote.
At 73, Jain is still running things, but he’s already handed the board a shortlist of potential successors.
The Man Behind Berkshire’s Billions
Jain’s deals were anything but ordinary. He wrote policies for Chicago’s tallest building against terrorism, protected Pepsi from a $1 billion sweepstakes payout, and insured baseball teams in case superstars like Alex Rodriguez got injured.
His success helped Berkshire collect massive lump sums from insurance premiums — not just to pay claims, but to keep the company’s cash pile growing.
Buffett famously told shareholders that if they could only save one Berkshire executive from drowning, they should “swim to Ajit.”
The Candidates for Jain’s Crown
Joe Brandon, CEO of Alleghany
Brandon, 66, is in his second stint with Berkshire, rejoining after its 2022 acquisition of Alleghany — a conglomerate with holdings in insurance, steel fabrication, and even Squishmallow toys.
He “understands both Berkshire and insurance,” Buffett said at the time of the purchase.
Brandon previously led General Re, one of Berkshire’s major reinsurance units, for seven years. He left in 2008 after federal prosecutors pressured Buffett to remove him following fraud convictions of four other Gen Re executives. Brandon was never charged.
Todd Combs, CEO of Geico
Combs, 54, wears two hats: CEO of Geico and one of Berkshire’s top investment managers. Under his leadership, Geico — the country’s third-largest auto insurer by premiums — has seen dramatic improvements in technology, earnings, and reserves.
Buffett called the transformation “spectacular.”
Between 2005 and 2010, Combs ran a hedge fund and generated a net cumulative return of 34% — compared to the S&P 500’s 1.15% during the same stretch.
But his experience with unusual or complex risks is limited, and some analysts think he may take on more of Buffett’s investing responsibilities instead.
Peter Eastwood, CEO of Berkshire Hathaway Specialty Insurance
Eastwood, 58, was recruited by Buffett from AIG more than a decade ago. Since then, he’s built Berkshire Hathaway Specialty Insurance (BHSI) from scratch.
The business became profitable within 15 months and now has more than $15 billion in reserves.
Buffett once said hiring Eastwood was “a home run.”
BHSI now operates across the U.S., Europe, Asia, and Australia. Still, the company remains smaller than other Berkshire units like National Indemnity Company or Gen Re.
Kara Raiguel, CEO of General Re
Raiguel, 52, has worked closely with Jain for over a decade. He once called her his “secret weapon.”
She took over General Re in 2016. Under her leadership, reserves have grown and pricing discipline has improved.
Ratings firm A.M. Best noted in November that Gen Re has made “significant” efforts to align pricing with risk.
Raiguel has spent nearly her entire career inside the Berkshire insurance ecosystem, giving her deep familiarity with its approach and culture.
An Industry in Transition
Whoever succeeds Jain won’t be inheriting the same landscape.
Over the past decade, traditional reinsurance capital has been challenged by pension funds and catastrophe bond investors. Meanwhile, private equity firms have entered life insurance and annuities.
Jain adapted by expanding Berkshire’s commercial insurance footprint — including Eastwood’s BHSI — and revitalizing Geico. For the past two years, Geico’s underwriting earnings have surpassed all other Berkshire insurance units combined.
The Real Legacy: Saying No
“He will be a very hard act to follow,” said Stephen Catlin, executive chairman of Convex.
Christopher Bloomstran, chief investment officer of Semper Augustus Investments Group, believes that Jain’s greatest contribution might not be his knack for making money, but his discipline.
“As long as Berkshire’s next insurance chief is also comfortable saying no,” Bloomstran said, the company will continue to benefit from the cash pile Jain helped build.
Jain, born in India, trained as an engineer before moving to the U.S. for Harvard Business School. He joined Berkshire in 1986 with no insurance experience and within six months was running the reinsurance business.
He earned a reputation for listening carefully, pricing conservatively, and only taking risks that paid off.
The Big Question Remains
Jain hasn’t said how much longer he’ll stay. Buffett and Jain declined to comment for the article, and Berkshire hasn’t revealed the names on the shortlist.
But whether it’s Brandon, Combs, Eastwood, or Raiguel — or someone else — stepping into Jain’s role means taking over one of the most important, and most profitable, pillars of the Berkshire Hathaway empire.
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