Warren Buffett has built his legendary reputation on making smart bets at the right time. While Berkshire Hathaway (BRK.B) might be trailing the broader market this year, one of his recent insurance plays is working out beautifully.

The Chubb Position Pays Off

Here's something interesting: with less than a month left in 2025, Berkshire looks likely to underperform the S&P 500 (SPY). That doesn't happen often for Buffett's conglomerate, which has beaten the benchmark in three of the last four years and 11 of the last 20.

But it's not for lack of smart moves. Berkshire's third-quarter activity included some notable decisions, like initiating a new position in Alphabet Inc. (GOOGL) and adjusting several existing holdings. The 13F filing revealed the firm cut five positions while increasing four others.

One of those increases was in Chubb Ltd. (CB), the insurance giant. Berkshire ramped up its Chubb stake by 16%, adding 4,299,111 shares to bring the total position to 31,332,895 shares by the end of September.

That bet is looking pretty good right now. Chubb shares have climbed 9.1% since September 30, delivering substantial gains to Buffett's investment empire.

The Numbers Behind The Gains

Let's break down what this means in actual dollars. On September 30, Chubb closed at $282.25 per share. That valued Berkshire's entire position at roughly $1.21 billion.

Today, with Chubb trading at $308.77, the stake is worth approximately $1.33 billion. That's a gain of more than $830 million on the position since the end of the third quarter. The shares added during Q3 alone have contributed over $114 million to those gains.

Berkshire first started accumulating Chubb shares in 2023, and the position remained confidential for a while as Buffett built out a meaningful stake. The company finally disclosed the holding in 2024 after establishing a sizable position, and by the end of the third quarter, Chubb had become the eighth largest holding in Berkshire's portfolio.

Strong Holdings, But Still Behind The Market

In dollar terms, Chubb ranks as one of the top performers in Berkshire's portfolio since September. The newly purchased Alphabet shares have also done well, making the tech giant a top 10 holding with significant gains since the purchase.

Despite these wins, Berkshire is still lagging the broader market. Berkshire shares have climbed 9.9% so far in 2025, while the SPDR S&P 500 ETF Trust (SPY) is up 13.3%.

With just weeks remaining before the year ends, there's a real possibility that Buffett's final year as CEO of Berkshire Hathaway will go down as one where the conglomerate underperformed the S&P 500. It's a reminder that even the Oracle of Omaha can't beat the market every single year, though his long-term track record remains enviable.

Still, that $830 million gain on Chubb? Not too shabby for a few months' work.