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2 Insurance Stocks to Buy With Dividend Streaks Longer Than 50 Years

2026-10-03 01:15 •Reuben Gregg Brewer •The Motley Fool Positive Axe Cap view: Selective •Rates•Equities•Capital Returns•Financials •CINF•RLI•PGR

Axe Cap view

Two US Insurance Dividend Kings Worth Watching

Cincinnati Financial and RLI boast decades of dividend increases, but differ in risk and valuation.

Dividend streaks beyond 50 years are rare and speak to disciplined capital management, especially in insurance where underwriting profitability matters. Cincinnati Financial (CINF) impresses with 66 years of consecutive increases and a 2.3% yield. However, its hefty 40% equity exposure makes it vulnerable during market dips—something South African investors should keep in mind if the rand weakens against the dollar, as that magnifies offshore equity risk. RLI, on the other hand, has a 51-year streak and trades at a cheaper price-to-book ratio than its usual range. Its lower 20% equity exposure and history of special dividends add a layer of upside, making it a cleaner dividend play. For rand investors, the main FX risk lies in USD/ZAR swings, but RLI’s valuation margin of safety could help in weaker-rand scenarios. The view might be wrong if US equity markets stabilize and widen spreads, lifting CINF’s valuation more than anticipated. this is just our opinion and not financial advice

How I would invest

Prefer buying RLI over Cincinnati Financial for dividend reliability at a discount and lower market risk. Trim or wait on CINF until equity exposure is less of a headwind or the yield rises meaningfully.

What I would watch
  • RLI
  • CINF
  • USD/ZAR
What could go wrong
  • USD/ZAR volatility impacting offshore earnings
  • US equity market downturn boosting CINF vulnerability
How strongly I feel

6/10

Cincinnati Financial and RLI are highlighted as Dividend Kings with 66 and 51 years of consecutive annual dividend increases, respectively. Cincinnati Financial offers a 2.3% yield but has higher equity exposure (40%) making it vulnerable in bear markets. RLI, with a 1.3% yield and 20% equity exposure, appears more attractively valued at a P/B ratio of 2.9x versus its 5-year average of 4x, and has a history of substantial special dividends.

Our take is based on reporting first published by The Motley Fool.

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