A Game Plan for the Future

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Stephen J.Sherman
Stephen J.Sherman

As a skilled knuckleball pitcher for the Boston Red Sox for 17 years, Tim Wakefield was methodical, deliberate and steady as he took his position on the mound. Turns out, those same skills have served him well off the field and are now proving just as valuable in his post-baseball life.

In 2005, as Wakefield was nearing the twilight of an illustrious major league career, he considered options that would help ensure he could retire wearing a Boston uniform. The then 38-year-old was married with a young son and a year earlier had bought his first home in the Boston area. To secure his spot on the team, Wakefield offered to do what no other player had ever done before: sign a perpetual option that guaranteed the team the same $4 million contract for his services year after year.

By doing so, Wakefield exchanged the choices that come with being a free agent for the certainty of playing for—and retiring from—the team he loved. “I told my agent that I didn’t want to sign with anyone else,” he recalls. “I wanted to stay in Boston. My wife and I had put down roots and the last thing I wanted to do was pick up and move.”

This pragmatic, hardworking approach to life began, Wakefield believes, with his family. “When I was younger and times would get tough, my father used to tell me to ‘bow my neck,’ which meant don’t give up, try harder,” he says. “He used to say, ‘Don’t let anyone tell you that you can’t do something.’ And that’s really always been how I approached my career.”

Wakefield employs this same deliberate, stay-the-course attitude in his life off the field. Despite the portrayal of baseball players as freewheeling spendthrifts, he says he has always been conservative with money. “When I got to the big leagues and was making that kind of paycheck, I started thinking about saving and what my finances would look like past my playing career. If I couldn’t pay cash for something, I didn’t. I saw so many guys get into deep debt and I knew I didn’t want that pressure. It doesn’t mean I won’t finance purchases; I just like knowing I have the money set aside to pay for them.”

Wakefield began thinking about life after baseball about six years before he actually left the game. The knuckleballer devised a long-term plan that took into account his conservative approach to investing, while also allowing him to maintain for himself and his family—which now includes a young daughter—the lifestyle he enjoyed as a player. “I’ve always tried to save as much as possible, and I don’t like a lot of risk with my investments, so it was important for us to get a good plan in place,” he says.

These days, Wakefield is putting his financial acumen to work as honorary chairman of the Red Sox Foundation, where he will coordinate fundraising events and community service days in New England. This 2010 Roberto Clemente Award winner for community service says giving back has been part of his life since his minor league days. “As an athlete I had a stage from which to give back not only to the communities where I lived, but where I played,” Wakefield says. “I was very blessed to put on a baseball uniform every day and play a sport for a living.” -Susan Caminiti

(MORE: See the second installment in this series Day by Day, Aiming to Do Better”)

(MORE: See the first installment in this series “A Steady Hand on the Throttle”)

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