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

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"Dogs of the Dow" is a popular investing strategy. By buying shares of the highest-yielding stocks on the Dow Jones Industrial Average (DJINDICES: ^DJI) market index, you can buy into top-quality companies whose shares are selling at a discount. In the long run, these struggling winners should overcome their challenges, transforming low-priced stocks with rich dividends into solid income generators with healthy share prices.

What if you wanted to apply that strategy to a larger pool of potential dividend heroes? The S&P 500 (SNPINDEX: ^GSPC) index is much larger than the Dow, and its component stocks were also handpicked among the top companies in America. There are more high-yield names on this list, and the top payers are much more generous than their Dow Jones counterparts.

So let's check out the top three dividend yields on the S&P 500. Are Walgreens Boots Alliance (NASDAQ: WBA), Altria (NYSE: MO), and Ford (NYSE: F) poised to recover from their current struggles in the long run? More to the point, do any of these high-yielding S&P 500 stocks look like great buys in the middle of December, 2024?

Walgreens yield: 12.2%

The convenience store and pharmacy retailer stands out in a couple of ways:

  • The 12.2% dividend yield is in a different class. No one else breaks the 10% barrier, or even the 8% level.

  • Walgreens stock has plunged 62% lower in 2024. Again, this stock has no real competition for this dubious honor.

  • The company is unprofitable on the bottom line, and its free cash flows are also negative over the last year.

  • Investors have caught on to Walgreens' troubles. 16% of its shares were sold short at the end of November, up from 5% in March. Again, no one else can compare to this pessimistic metric.

The transatlantic store chain boasts impressive revenue growth in recent years, but has failed to convert the sales into bottom-line profits. The turnaround attempt isn't working out, and management has reportedly talked to private equity firm Sycamore about a leveraged buyout. Even that desperate exit idea seems unlikely, as the deal-financing banks would insist on a profitable long-term business plan. As the pharmacy business continues to move online, Walgreens is left with an expensive and unprofitable store network, financed by a burdensome $9.5 billion of long-term debt.

This juicy dividend is not connected to a slam-dunk turnaround effort. In cases like this one, extreme yields serve as red flags -- Walgreens has serious business issues and it's probably best to avoid the stock.