On December 6, 1989 — Joe Carter is sent by the Indians to San Diego for Chris James, Sandy Alomar and Carlos Baerga.

The Friars had a very nice problem in the late ’80s. They had Benito Santiago, who was a flashy, young catcher with a tremendous arm and an equally dangerous bat. Santiago was still very young at the time, and the team’s #1 prospect happened to be a catcher as well. Sandy Alomar Jr. was considered a can’t-miss catching prospect, who had a very similar skillset to Santiago. The Padres had a huge decision to make. Should they deal the young, unproven phenom or trade Santiago?

They chose to move Alomar as they packaged him with two other young prospects for a proven veteran outfielder. Joe Carter was coming off a season where he played in all 162 games for the Indians and hit 35 homers with 105 RBIs. Carter responded in 1990 by hitting .232 with the Padres in 162 games. He hit 24 home runs and drove in 115 runs that season. He was traded 364 days after being acquired by the Padres as Carter was packaged with Roberto Alomar for Fred McGriff and Tony Fernandez on December 5th, 1990, in a trade that still hurts most Padres fans. Roberto Alomar would go on to have a Hall of Fame career.

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Sources:

https://www.eastvillagetimes.com/padres-history-three-trades-happened-on-this-date-2/