I know I'm probably the only Indians fan on here, but in the opinion of non-Tribe fans, which was the worst move by the Indian's front office
1) Shoeless Joe Jackson for Braggo Roth. The only player the Naps (wouldn't be the Indians for a few more years) had on the team with any drawing power, Cleveland trades Jackson to the White Sox for Roth and $35,000. Attendance plummets and Cleveland starts the intelligent trend of sending their best players away in an attempt to make money
2) Rocky Colavito for Harvey Kuenn. The most popular Indian possibly ever sent to Detroit. Colavito led the league in home runs the next season, Kuenn played the next season, then retired. Known as the "Curse of Colavito" it IS THE REASON the Tribe hasn't won a World Series since 1948 (no reminders of the Reds win of 1990, Hollister Hero)
3) Norm Cash for Steve Demeter. Another trade to Detroit. Cash hit close to 400 home runs after the trade. Demeter had exactly five at bats after the trade.
4) Roger Maris for Vic Power. Maris is known as the man who broke Ruth's single season home run record. Power is known as the first Puerto Rican to play for the Philadelphia A's.
5) Manny Ramirez to free agency. I guess the only thing to say here is "2007 American League Championship Series" when Manny and the Red Sox crushed the Tribe's dreams
6) Jim Thome to free agency. In 2002 Thome was voted by the Cleveland Plain Dealer as "Cleveland's most popular athlete" In 2003 he led the league in home runs, the National League, for the Philadelphia Phillies