Should You Buy the 3 Highest-Paying Dividend Stocks in the S&P 500?

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The power of owning dividend-paying stocks is often underappreciated. Consider, for example, that a study by Hartford Funds and Ned Davis Research found that between 1973 and 2023, companies that grew or initiated dividend payments delivered annualized returns of 10.2%, while dividend non-payers delivered only 4.3% (and an equal-weight S&P 500 fund averaged 7.7%).

Healthy and growing dividend payers will tend to have stock prices that rise over time, while paying dividends that are also increased over time. Given that stock profile, you might think it's smart to snap up the fattest dividend yields you can find -- perhaps focusing on the biggest dividend yields in the S&P 500.

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Here's a look at why you might want to think twice before taking this approach.

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Fat dividend yields: Good or bad?

It's important to understand what a dividend yield is. It's a ratio, typically expressed as a percentage, where a stock's total annual dividend amount is divided by its current stock price. So imagine the hypothetical Buzzy's Broccoli Beer (ticker: BRRRP), recently trading at $50 per share and paying out $0.50 per quarter -- which is $2 annually. Divide that $2 by $50 and you'll arrive at 0.04, or a dividend yield of 4%.

Companies usually pay dividends quarterly, and their dividend amounts generally stay the same for one or more years. Company share prices, though, change frequently. So the dividend yield changes frequently, too, by at least a little. Remember that the ratio is the dividend divided by the stock price. So if the stock price rises sharply, the yield will fall -- and vice versa.

Thus, an especially fat dividend yield may be the result of a stock having plunged, and not simply reflecting a super-generous business. Therefore, it's always smart to look at a fat yield extra closely, to see if the company is facing any trouble.

Below are three companies that were the highest-yielding stocks in the S&P 500 recently. Let's take a closer look at each.

1. Walgreens Boots Alliance

Walgreens Boots Alliance (NASDAQ: WBA) was recently sporting a massive dividend yield of 12.1%. That certainly looks enticing. Invest, say, $10,000 in Walgreens and collect $1,210 over the year! But hold on -- a closer look at the company will reveal that it's been struggling recently. The stock was down almost 65% year to date as of this writing, and down 21% just in the past month.