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In 2020, he told the St. Louis Post-Dispatch that he was "absolutely not" content with what he accomplished in his career.

In 2017, Jefferies was working as a hitting instructor at Office Sports Academy in Anaheim. By 2020, he had relocated to Las Vegas, Nevada where he was working as a freelance hitting instructor.

Tigers manager Phil Garner offered Jefferies the bench coach job for 2001 but he declined.

After playing the 1992 season with the Royals, he moved on to the St. Louis Cardinals, where he would have his two best seasons, batting .342 and .325, respectively, while finding a home at first base and being named to the National League All-Star team in both the 1993 and 1994 seasons. He signed a lucrative contract with the Philadelphia Phillies after the 1994 season due to a dispute over a no-trade clause the Cardinals wouldn't give him, and he moved to the outfield for the Phillies, where he performed adequately over the 1995, 1996 and 1997 seasons, but injuries to his thumb and hamstring hampered his effectiveness. In 1998, he was traded mid-season to the Anaheim Angels, where he hit .347 in 19 games before moving to the Detroit Tigers the next year. He hit a collective .231 for the Tigers over two seasons before he retired in 2000 due in part to a severed right hamstring.

In response to criticism from teammates, on May 24, 1991, Jefferies pleaded his case in an open letter read on WFAN, New York's sports radio station. In the letter, Jefferies wrote: "When a pitcher is having trouble getting players out, when a hitter is having trouble hitting, or when a player makes an error, I try to support them in whatever way I can. I don't run to the media to belittle them or to draw more attention to their difficult times. I can only hope that one day those teammates who have found it convenient to criticize me will realize that we are all in this together. If only we can concentrate more on the games than complaining and bickering and pointing fingers, we would all be better off." In 2020, Jefferies denied having written the letter but would not reveal its true author or authors.

In 1990, Jefferies raised his batting average to .283 while scoring 96 runs and leading the NL with 40 doubles, but the Mets finished 2nd for the second straight year. He slipped in 1991, hitting .272 with 30 extra base hits in 486 at bats as the team slipped to 5th place. That off-season the team traded him, along with McReynolds and infielder Keith Miller, to the Kansas City Royals for former All-Star pitcher Bret Saberhagen and utility man Bill Pecota, ending his stay with the Mets.

The Mets made a full-time roster spot for Jefferies when they traded Wally Backman to the Minnesota Twins, leaving second base open for Jefferies. But Jefferies faltered, hitting .258 with little selectivity as a rookie in 1989.

The Mets decided they needed to make room for Jefferies, but didn't know where to play him, as the veteran team was full at the spots Jefferies played in the minor leagues (shortstop, third base and second base). The outfield was full as well, with the team finding it difficult to get outfielders Lenny Dykstra and Mookie Wilson playing time alongside Darryl Strawberry and Kevin McReynolds, so Jefferies was sent to AAA Tidewater to start the 1988 season.

Drafted by the New York Mets out of Junípero Serra High School in the first round of the 1985 amateur draft (#20 overall), Jefferies hit .331 in his first year in the minor leagues, moving from Kingsport of the Appalachian League (rookie) to Jackson of the Texas League (AA) in two years. He was named Baseball America's Minor League Player of the Year for both 1986 and 1987, becoming the first player to receive that distinction in consecutive years. He hit .367 with 20 home runs, 48 doubles and 101 RBI for Jackson in 1987, earning Jefferies a brief call-up from the New York Mets at the end of the 1987 season. He went 3 for 6 in 6 games, at the age of 19, making him the youngest player in the Major Leagues that season.

Gregory Scott Jefferies (born August 1, 1967) is a retired infielder/outfielder in Major League Baseball who had a 14-year career from 1987 to 2000. He was a highly touted prospect who became the first two-time winner of the Baseball America Minor League Player of the Year Award. On August 25, 1995 in a game vs the Dodgers at Veterans Stadium Gregg Jefferies became the first Phillie to hit for the cycle since Johnny Callison in 1963. In 2017, Baseball America called him their most highly regarded prospect until Andruw Jones. He went on to become a two-time All-Star.