Nailed!: The Improbable Rise and Spectacular Fall of Lenny Dykstra is a tragedy, but it is not a particularly novel one. It’s about an athlete who goes bad after retiring. What’s different is that it was close to playing out as a success story.

Lenny Dykstra was a star with the New York Mets, helping them win the World Series in 1986. After retiring, he taught himself how to pick stocks and manage his money. He started making regular appearances with Jim Cramer, and he hit upon a fabulous idea: set up a business to advise athletes on how to manage their post-career lives. He set it up as a club — the Players Club — and it would provide perks, support, and financial information. It filled a need.

The post-playing track record of most athletes isn’t very good.  Sports Illustrated has reported that within five years of retirement, 60% of former NBA players are out of money. Within two years of retirement, 78% of former NFL players  are broke or in financial distress.

Athletes receive a large sum of money in a short period of time, and then that money has to last the rest of their lives. Few of them majored in finance in college, or have the kind of practical experience that forces many people into strict financial discipline (such as trying to pay rent, build a work wardrobe, and pay off student loans on an entry-level salary). They work on their sport. In a culture that worships athletic prowess, they are the alphas, the stars, the heroes.

Until they aren’t.

Until they are retired, out of shape, just another guy trying to get a room upgrade. Good luck with that, buster. That’s why Dykstra’s idea was so great. He knew what these people were going through; he wasn’t just another advisor trying to make a buck.

The Players Club started as a magazine, a glossy publication that was distributed to professional athletes in the locker room. The few issues that were published has glossy profiles, lifestyle articles, and financial advice.

This story has three threads. The first is the difficulty of a good second career for an athlete. The second is how an entrepreneur’s passion sometimes conflicts with the realities of running a business. And the third is age-old: people screw up when drugs and alcohol are involved.

The author, Christopher Frankie, was a huge Mets fan as a kid; he had a poster of Dykstra on his wall. He was working in financial journalism when he received to offer to become editor of the Players Club. He jumped at the chance to work with his hero on a good idea, and he quickly became enmeshed with a manager unable to focus on a single idea, treat employees with respect, or manage cash.

Frankie has some scores to settle, yet he remains mostly sympathetic to Dykstra — at least until Dykstra’s  jerkiness became too much to bear. Frankie wants the business to succeed because it’s a good idea. But it fails, mostly due to errors of Dykstra’s own making. Dykstra wouldn’t listen to people who actually knew something about publishing. He ran up his expenses so that people in entry-level jobs couldn’t get their paychecks, skipped out on hotel and private jet bills, and got into fights with freelancers.

Ultimately, the Players Club fell apart. Dykstra returned to drugs and alcohol after years of sobriety, and ended up divorced and broke. He was eventually sentenced to prison for three years on auto theft (he told the dealer he was buying the cars, then took them off the lot without paying) and another 6 1/2 months on bankruptcy fraud, concealment of assets, and money laundering.

This book is compelling. Unfortunately, it’s not as original as one would hope, but that’s not Frankie’s fault. It’s not news that athletes get in trouble when their playing careers end. Dykstra’s story would be more notable if he had succeeded.

The Players Club was a great idea, and Dykstra, it turns out, needed it more than most. Now he can worry about a post-prison career as well as a post-playing career.

Tagged in:


About the Author

Ann Logue

Ann Logue is a freelance writer and consulting analyst who is fascinated by business and technology. She has a particular interest in regulatory issues and corporate governance. She is the author of "Emerging Markets for Dummies" (Wiley 2011), “Socially Responsible Investing for Dummies” (Wiley 2009), “Day Trading for Dummies” (Wiley 2007), and “Hedge Funds for Dummies” (Wiley 2006), and has written for Barron’s, Institutional Investor, and Newsweek Japan, among other publications. As an editor and ghostwriter, she worked on a book published by the International Monetary Fund and another by a Wall Street currency strategiest. She is a lecturer in finance at the University of Illinois at Chicago. Her current career follows 12 years of experience as an investment analyst. She holds a B.A. from Northwestern University, an M.B.A. from the University of Chicago, and the Chartered Financial Analyst designation. How's that for deathly dull?

View All Articles