St. Louis Cardinals manager Tony La Russa, who just led his team to the 2011 World Series win, announced his retirement on Monday. (Kathy Willens/ASSOCIATED PRESS)

Surely, Mozeliak doesn’t admire La Russa because he thinks it’s time for him to retire. The 33-year veteran of the major leagues has six pennants to his name—three each in the National and American Leagues—and three World Series wins, making Mozeliak’s job of replacing him that much harder. After all, who wants to follow in a legend’s shoes?

Rather, his admiration is likely because he knows how hard it is for most leaders to step out when they’re on top, making their exit when the spotlight is bathing them in its warmest glow. There are several reasons this happens. For one, let’s be honest here, it’s easiest to negotiate the next blockbuster employment contract with a huge salary bump when you’ve just achieved the greatest feat in your game. Even if you’re the guy in charge, someone wants to keep you—whether it’s a board of directors, a team owner or party leaders—and saying no to all those dollar signs can be very hard, indeed.

Such success also makes it easy for leaders to forget the harder parts of their job. When you’ve just won the World Series, or reported a great quarter, or are doing well in the polls, it can be easy to forget the error-filled games, the economic havoc of the year before, or the party infighting that makes the job so frustrating. “I can do this a few more years,” such leaders think, blinded by the rosiness of the moment.

Yet another reason some leaders don’t walk away when they’re on top is that once they do, changing the story line becomes nearly impossible. They can’t be there to fix a mess that could undo their legend, make the personnel changes that will keep the organization strong after they leave, or reinforce the culture that helped them lead their team to success. Once they leave, outsiders might blame it on their successors. Or they might say what they built wasn’t as strong as what everyone believed.

Most of all, we’re all human, and once we taste the sweetness of success, we want to have it again. In the cushy afterglow of achievement, the idea of giving it all up for the unknowns of retirement feels empty and foreign. The temptation of reaching that goal again—be it a championship win, a record quarter or another election—is all too strong.

Some leaders, like La Russa, are smart enough to resist that tug. In other cases, such as Samuel J. Palmisano’s recent decision to retire from IBM while the company is performing well, they were pushed toward making it. Traditionally, IBM CEOs have retired at 60, and Palmisano hit that milestone this year.

Maybe more organizations need to have such a tradition in place. If more created term limits or retirement ages, they might prevent leaders from being tempted to stay on past their prime, suffering from overconfidence, or racking up outsized pay packages that balloon after a big win. After all, even the strongest leaders can be weak when it comes to ending it all. By setting the finish line for them, we might save them from themselves.

More from On Leadership:

Is Tony La Russa the best manager in baseball?

How to be a great boss

Mr. Schmidt goes to Washington

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