San Diego proved to be a much sunnier climate for Sheffield. Management let him alone, and Sheffield had his first injury-free season. It was a highly productive one: He batted .330, leading the National League, with 33 home runs and 100 RBI, nearly winning the Triple Crown, and the Sporting News named him Major League Player of the Year.
The Padres, however, faced a financial crisis and shipped Sheffield to Florida during the 1993 season to save on salary. The Marlins moved him from third base to the outfield, where he worked on his notoriously poor defense and began to cut down on his errors. Sheffield also dramatically increased his walk totals.
Sheffield's return to his home state landed him in plenty of off-field trouble. He was accused of threatening his son's mother. A complaint of aggravated battery was lodged against him. Sheffield's mother was the target of a murder plot. He was stalked by a female fan, was convicted of drunk driving, had an ex-girlfriend file a lawsuit against him, and he fathered a third child out of wedlock. One night, while sitting at a traffic light in Tampa, Sheffield was shot, but luckily the bullet only grazed him. When Gooden ran into well-publicized troubles with a cocaine addiction, Sheffield was frequently searched and tested for drugs. With all these distractions, he had another bout of injuries and his playing time shrank in 1994 and 1995. At one point, though, Sheffield had eight consecutive hits during the 1995 season.
In 1996, Sheffield hired a public relations agent, started his own charity, took lessons in public speaking, posed for a fashion magazine, and moved to Miami. All these efforts at repairing his image and avoiding off-field trouble paid off on the field, as well, with his second excellent season. He hit .314 with 42 home runs and 120 runs batted in.
At the start of the 1997 season, Sheffield became the richest player in baseball by signing a six-year, $61 million contract extension. Pitchers decided to pitch around him, and Sheffield, notorious for his frequent strikeouts, decided to stop swinging at bad pitches. He slumped to.250, but he had 121 walks, 21 home runs and 71 RBI. For the rest of his career Sheffield always enjoyed high on-base percentages. He was frequently on base during the 1997 playoffs and World Series, which the Marlins won in their first and only post-season appearance, hitting .320 for the post-season with a remarkable .514 on-base percentage.