He was hired as a special assistant in the front office of the Florida Marlins

Dawson joined the Boston Red Sox as a free agent on December 9, 1992. It was a transfer to Fenway Park's second hitter-friendly venue. Additionally, the slugger made his first career shift to the American League, allowing him to play outfield and occasionally serve as the designated hitter to rest his knees. He believed that if he played for a few more seasons, he would have 3,000 hits and 500 home runs. However, during the season, Dawson tore more cartilage from his knee, and his advanced age was beginning to show. He only hit 13 home runs, including his 400th career blast, and he was considering retiring.

But on April 10, 1995, Dawson joined the Florida Marlins and went back to the National League. Before retiring after the 1996 season with 438 home runs, 1,591 RBIs, 2,774 hits, 314 stolen bases, and 1,373 runs scored, he played largely as a pinch-hitter for two seasons. The only players in Major League Baseball history with more than 400 home runs and more than 300 stolen bases are Dawson, Willie Mays, and Barry Bonds. He was an eight-time All-Star and the recipient of eight Gold Gloves. He was hired as a special assistant in the front office of the Florida Marlins.