Ever the fresh-faced youngster, the versatile Jefferies jumped from team to team throughout his career, but consistently boasted an array of offensive weapons, fine average, moderate power, and one of the best walk-to-strikeout ratios in the majors. Jefferies was even a threat on the basepaths — stealing as many as 46 bags one year — until a string of injuries slowed him down. His ability to play a variety of infield and outfield positions at least adequately made Jefferies a valuable asset to any of his teams.
From early on in his career, Jefferies’ odd batting habits drew attention from the media. At an early age Jefferies was introduced to an extensive training regimen with his father that involved building strength by swinging a bat underwater. He also had an odd attachment to his bats — instead of putting them in the team’s equipment bags, Jefferies carried them himself. Though he didn’t go so far as to sleep with them (as teammate Kevin Elster reportedly did), he did rub alcohol on them to remove the nicks and pine tar.
His attentiveness to batting was quickly rewarded. Jefferies was the Mets’ first-round pick in the June 1985 draft and a minor league MVP each of his first three seasons. He had an outstanding late-season call-up in 1988, hitting .321 with six homers in 109 at-bats, eventually pushing the slumping, injured Howard Johnson off third base for the NLCS.
Jefferies’ strong 1988 display convinced manager Davey Johnson and the organization to trade incumbent second baseman Wally Backman to make room for him. But though Jefferies was given the second base job from the start of the 1989 season, he went through a horrible slump in the first two months, showing very little selectivity at the plate. Johnson stuck with him, and Jefferies eventually came around, finishing with a respectable rookie mark of .258. But despite the relatively strong finish in ’89, Jefferies’ relationship with New York — and especially the New York press — had turned turbulent, at best.
Jefferies was touted as the best thing to come out of the Mets farm system since two kids named Dwight Gooden and Darryl Strawberry, but he couldn’t live up to the unearthly precedents of his two predecessors. As the media buzzed and Met veterans began to resent all the attention he was receiving, Jefferies became at times aloof, and at other times immature. His violent, emotional outbursts at his strikeouts and poor defensive play soon led New York papers and radio stations to mock him constantly.
Jefferies remained with New York for two more seasons, but it appeared that he would not be the star that the organization had originally thought him to be. In December 1991, the Mets traded the infielder along with Kevin McReynolds to the Kansas City Royals for a much-needed pitcher, Bret Saberhagen. Though he batted adequately for KC in 1992, the Royals needed a little more pop than contact hitter Jefferies was giving them. On the heels of a 90-loss season, the Royals traded Gregg to the St. Louis Cardinals for promising switch-hitting outfielder Felix Jose and utility infielder Craig Wilson in February 1993.
Without the berating press of New York or lackadaisical fan support of Kansas City, Jefferies found St. Louis to be one of the best cities in the nation for baseball. He flourished under the caring eye of manager Joe Torre, batting .342 with 46 bases in 1993, and .325 in ’94, being selected as an All-Star both years. Torre also switched Jefferies over to first base, a position at which he would end up platooning for the rest of his career.
Perhaps it was a bit of his old immaturity seeping back when Jefferies left the Cards to sign with the Philadelphia Phillies in December 1994. When St. Louis didn’t offer the first baseman a no-trade clause in a proposed contract, Jefferies scornfully told the Cardinals that, “if they keep letting free agents go, it’s going to be tough to win.” Gregg signed with the Phils, switching to the outfield at the organization’s request.
With Philadelphia, Jefferies performed adequately, but not as well as could have been expected from his St. Louis days. Fighting injuries to his thumb and hamstrings, he saw his power and speed dip somewhat over the course of his four years at Veterans Stadium. Jefferies had become more of a spray-singles hitter, and Philadelphia needed more. Though Gregg kept his batting average consistently around .300, he didn’t expect to be in the Phils’ plans past 1998 — and he was right. He was traded to the Anaheim Angels for a player to be named later for the homestretch of the AL West division race in August 1998.
In the offseason, Jefferies signed with the Detroit Tigers, playing a variety of positions in the outfield and infield. However, plagued with injuries to his hamstrings and elbow, Gregg managed just 111 games over the 1999 and 2000 seasons. When the Tigers didn’t offer him arbitration, he retired in December 2000 at the age of 33.