It started early in his first Major League stop, with the Milwaukee Brewers, where he was viewed as an extraordinarily talented young prospect, but never quite understood as an individual. In his first full season with the club, he was moved from shortstop to third base. He was outraged at this move. Shortstop was the place where the star played. Third bace was for somebody who wasn't good enough to play short.
Worse, he had been moved to third to make room for Billy Spiers, a rookie who had come up from Double-A. Sheffield had come up through the Minors in less than three years, but he had made stops at each Minor League level.
Sheffield spoke out publicly about what he perceived as mistreatment, at one point saying: "I should have been here years ago."
When he said that, he was barely 20 years old. Had he been in the Majors "years ago," the Brewers would have been guilty of violating numerous child labor laws.
Milwaukee was the one place where Sheffield would not succeed. He had injuries, illnesses, and he was never remotely contented. He was basically an angry young man. Later, he would become an angry full-grown man, but by that time his talent was receiving its due from the baseball world.
Traded to the San Diego Padres before the 1992 season, he responded to the change of scenery by winning a batting title. Thus was set in motion the pattern that defined his career.
For somebody who looks like a Hall of Fame candidate, he has played for a lot of organizations -- seven now. He would be traded somewhere, and life would be good. He would be appreciated, he would be respected and he would respond with tremendous performances.
And then, there would be problems. Maybe the contract was no longer suitable, maybe people were taking him for granted. Controversies would emerge and Sheffield would eventually move on. He has been with the Marlins, where he was part of a World Series championship team in 1997, then the Dodgers, then the Braves, then the Yankees, finally the Tigers.
On the plus side, there was always his remarkable offensive ability. "Over the last 10 seasons, year-in, year-out, he may have been the most dangerous clutch hitter in the game," one Major League scout said.
You have seen the classic Sheffield action; standing at the plate, doing that elaborate waggle of the bat. Your thought is: "He can't possibly be ready for the pitch, doing that." And the next thing you know the ball is in the left-field corner. The bat speed, the timing, the reflexes, the instincts, all separating him from the crowd, even at this level.
And he has played hurt, repeatedly, often almost habitually in his later years. He was asked earlier this year what it would be like to play pain-free and he smiled and responded: "I don't know if I remember how."
Plus, you have to give him this much on a personal level: He's honest. He may be too honest. He says things that will create controversy, things that other players would simply not say because of the difficulties that would ensue. Sheffield is more comfortable making the statements and dealing with the difficulties than simply keeping quiet and staying out of trouble.
"He has no filter," a teammate once said.
Sheffield has frequently touched a raw nerve, because over the years he has periodically contended that his problems stem from the fact that he is not simply outspoken, but an outspoken African-American. To Sheffield, this explains many of the difficulties he has had, with a variety of people in the game.
Age has not led him to ease up in these areas. Just last season he said in a magazine article that there were more Latin American players in the game now and fewer African-Americans, because it was easier for Major League Baseball "to control them." Sheffield later said that he meant "nothing derogatory" toward the Latin American players. But he also said: "They have more to lose than we do. You can send them back across the island. You can't send us back. We're already here.
"Bottom line, what I see, I talk about. ... I see it over and over. If anybody can show me I'm wrong, then show me."
That last comment has been close to a credo for Gary Sheffield. And very few people have been able to demonstrate to him that he has been wrong. Even this year, a season marred early on by injury, there has been a dispute with Detroit manager Jim Leyland over playing time and the fact that Sheffield has been used as a DH rather than in the outfield. Leyland pronounced himself "flabbergasted" over Sheffield's remarks.
All in all, over the bulk of his career, it has been impossible to take Gary Sheffield lightly, when he is facing notebooks and tape recorders, or more to the point, when he is facing the best pitching in the game.
But on his side of the argument, there have always been the numbers -- a career on-base percentage, for instance, of nearly .400. And now, there will be the 500 home runs, indisputable evidence of Gary Sheffield's worth.