5 Insurance Stocks to Buy for a Decade of Rising Dividends

How do insurance companies make money? While they aim to profit from underwriting, gains from investing premiums, also known as the "float," ahead of paying out claims, is another vital income stream for the industry, particularly for property and casualty (P&C) insurers.

For insurers successful at underwriting at breakeven or profitable levels and at successfully investing the "float" in steady fixed-income investments, this has created the ability to consistently pay out and raise dividends over time. Hence, if you are a long-term, dividend-focused investor, you may want to consider adding a basket of these insurance stocks to your portfolio.

Each of the stocks below has a strong prior track record of dividend growth, with a strong chance of this trend continuing in the decade ahead: Aflac (NYSE: AFL), Chubb (NYSE: CB), Cincinnati Financial (NASDAQ: CINF), Old Republic (NYSE: ORI), and Travelers Companies (NYSE: TRV).

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Aflac is a dividend and buyback legend

Aflac has raised its dividend for 45 consecutive years. Currently, the stock has 2% forward dividend yield. While this may sound modest, keep in mind that Aflac has historically raised its payouts at relatively high rates, with dividend growth averaging 11.4% over the past decade.

The insurer also has a long track record of share repurchases. Since 2022, Aflac's outstanding share count has fallen by nearly 100 million, or nearly 16%. This has helped steadily boost earnings and share appreciation, with the stock rising nearly 250% during this time frame.

Admittedly, what has worked over the past decade may not work as strongly in the decade ahead. Aflac's latest dividend increase was only 5.1%. The company's flagship Japanese unit also continues to experience a slowdown in premiums earned. Still, until more signs emerge that this slowdown represents the "new normal" for Aflac, consider it a strong choice for dividend growth investors.

Chubb remains a P&C 'masterpiece," and a top Berkshire holding

Last summer, Barron's referred to Chubb -- purveyor of policies like its "Masterpiece" high-end homeowner's insurance policies -- as a "masterpiece" among insurance companies. This moniker appears justified, given the company's continued strong track record of underwriting profitability. Strong underwriting profitability has also given way to strong earnings, dividend, and share price growth over the five years, with the stock delivering total returns of 105%, topping the S&P 500's 83% return during the same time frame.

So, what lies ahead for Chubb over the next 10 years? Perhaps more of the same, if current trends persist. Although near-term factors like higher catastrophe losses and more selective underwriting affected net income and premium growth, Chubb announced record net investment income, and indicated it would soon realize a $460 million gain on its $740 million investment in USI Insurance services. Moreover, year-to-date, Chubb's EPS is up 16% compared to the comparable period in 2025.

Assuming Chubb maintains high underwriting discipline, plus a greater focus than average on long-term book value growth, shares appear well positioned to deliver further strong total returns. That said, if the coming quarters bring about subpar income and underwriting growth, that could be a sign that this "masterpiece" insurer is losing its luster.

Keep an eye on quarterly results, as well as on other factors, such as if Greg Abel, Warren Buffett's successor at Berkshire Hathaway, decides to keep the stock as a top holding or begins to pare down Berkshire's 8% stake in the insurer. At current prices, Chubb has forward dividend yield of 1.15%, a 33-year track record of consecutive dividend growth, with payouts increasing by an average of nearly 4% over the last decade.

Cincinnati Financial is a Dividend King

For 66 years in a row, Cincinnati Financial has raised its dividend. Currently, the stock trades at a nearly 2.2% forward dividend yield. Over the past decade, dividend growth has averaged nearly 7% annually, with recent dividend increases in the high single-digits.

With this track record, Cincinnati Financial is one of the Dividend Kings, or stocks with at least 50 years of consecutive dividend growth. In terms of other positives, or at least Cincinnati's prospects for the decade ahead, admittedly, there are a few areas of concern in the short-term. During Q2, for instance, the insurer reported underwriting losses, with its combined ratio exceeding 100%.

Strong investment gains have helped to make up the difference, but with its investment portfolio skewed more strongly toward equities, with 40% invested in stocks, a broad market downturn could temporarily impact this aspect of the overall business.

That said, as this more stock-heavy approach has likely helped, not hindered, the stock's long-term total return, I wouldn't let such concerns, while present, serve as a "dealbreaker" for the stock. Moreover, with its manageable payout ratio of 42%, these potential near-term risks are unlikely to affect Cincinnati Financial's ability to maintain its Dividend King status.

Old Republic is a Dividend King in the making

Old Republic, with a 46-year record of consecutive annual dividend growth, is a Dividend King in the making, just four years away from clinching this status. Yes, with Old Republic's focus on the title insurance market, and the ongoing housing slowdown affecting this segment of the space, concerns about future payout and stock price growth appear warranted.

After all, as seen in Old Republic's latest quarterly results, net income, or income before investment gains and losses, fell from $279.5 million during Q3 2025, to $243.2 million in Q3 2026, a nearly 13% drop. That said, despite lower earnings, Old Republic reported a nearly 9% jump in net premiums during the quarter, and a 5.7% increase in book value over the past year. Recent results could affect Old Republic's special dividend this year. Last year, the special dividend added $2.50 per share to annual payouts.

However, with its 39% payout ratio, relative to its core annual dividends of $1.26 per share, the insurer appears in good enough shape to maintain its dividend growth, paving the way for it to reach Dividend Kings status. Over the next few years, a rebound in the housing market could bode well for the title segment, spurring a resurgence in growth. Currently, the stock has a forward dividend yield of 3.1%, with the potential for future special dividends to further boost said yield.

Travelers' banner year could give way to a strong decade ahead

Travelers Companies has crushed it over the past year, with the P&C insurer's shares gaining by around 50%. Chalk up the banner year to continued strong quarterly results. Travelers handily beat Wall Street estimates for Q3 2026, with EPS of $9.18 well ahead of forecasts calling for $7.39. Q3 earnings also represented a 12.7% increase from the prior year's quarter.

That said, can this banner year give way to a banner decade? On the surface, it's questionable. Much of Travelers' strong results can be chalked up to strong investment gains, not to underwriting growth. On the other hand, longer-term metrics for Travelers suggest the potential for it to remain one of the top dividend growth stocks, even if future price appreciation comes in far less rapidly than over the last 12 months.

Travelers has a 22-year track record of consecutive dividend growth, and a payout ratio of just 16.1%. Management has plenty of room to keep on implementing dividend increases. Travelers' most recent dividend increase was nearly 11.5%, suggesting management is already accelerating the dividend's growth.

The insurer could be more vulnerable to a reversal in operating performance and stock price, but with shares still reasonably valued, at around 11 times forward earnings, downside risk could be vastly exceeded by the potential for Travelers to keep emerging as one of the top long-term dividend growth stocks. Currently, shares have a forward yield of 1.25%.

Thomas Niel has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Berkshire Hathaway. The Motley Fool has a disclosure policy.