May spent 18 years in professional baseball as a player, including 10 seasons in the Major Leagues with the Cubs, Astros, Phillies, Expos and Orioles. His best season at the Major League level came in 1993 while playing for the Cubs. May hit .295 that season, to go along with 10 home runs and 77 RBI.
"It's a little like being in heaven," recalls May, remembering back to playing left field at Wrigley Field.
But his time in Wrigley Field or any other Major League ballpark for that matter, is nothing like the experience May got during the last three years of his playing career, because those seasons were played in Japan.
Playing in Japan was something May had always thought about.
"I knew about Japanese baseball for a while," he says. "When I was in the Minor Leagues, there were a few guys who went over to Japan and got the opportunity to play over there, so it was always in the back of my mind. I got to a point where I felt I could still play. The opportunity came up where they wanted me, and I stayed for three years. Most guys don't stay that long."
May took advantage of his time in Japan, belting 23 home runs for Chiba Lotte in 2003, while batting .273 and driving in 93 runs. A foot injury cut his career short, but he felt it was time to move on all the same.
Most people have only experienced Japanese cultures through movies such as Lost in Translation, which May says is pretty accurate, but there are nuances to Japanese baseball that fans, and even players, don't realize. For May, it was fairly easy to adjust to the culture because he had an open mind about it.
"If you embrace the culture," he says, "they embrace you."
"They play a different way," says May, "and you have to understand that. (Japanese players) are very safe, and not very aggressive. They play very fundamental baseball, and (most guys) don't rely on their instincts. They're taught a certain way and they stick to it.
"They believe in a team concept. As much as you're not from there, they believe you should be part of it. There's a saying that if you can eat with chopsticks, you can hit in Japan, which means you've taken to their culture. If you don't try to do that, you slip through the pores."
Now that Derrick May is back in the states, he feels fortunate about the opportunity he's been given in the Cardinals' organization. As a first-year coach, he was not sure what to expect when he got here.
"I was kind of nervous at first," May remembers, "but it's a great organization and there are great people around here. You really don't know how the players will take to you, but the players here are really good character-wise, (in Palm Beach) and throughout the organization."
May will typically arrive at the ballpark around noon for a 7:05 game and spends time reviewing film and working with the players in the batting cages.
Regarding his coaching technique, May says, "I can teach (the players) all the mechanical things, but there are certain things they have to do for themselves. The one thing they can control is their emotions and their approach to the game and each at bat.
"I want them to understand that the preparation for the game, and evaluating after the game, are the keys to success. Understand the moment and learn from it, and that'll make you a better player."