Credit: Matt Marton-USA TODAY Sports
#3: Trading Brandon Phillips
Heading into the 2006 season, Brandon Phillips, the former top prospect, was out of minor league options after struggling to establish himself in the big leagues. It appeared as though he would make the club as a utility player behind starting 2B Ronnie Belliard; however, manager Eric Wedge felt Ramon Vazquez was a better fit on the bench than Phillips. Phillips, who had a reputation of being a bit of a prima donna, was designated for assignment at the end of spring training by the Cleveland Indians.
Mark Shapiro then dealt Phillips to the Cincinnati Reds for minor league reliever Jeff Stevens. Phillips became the starting 2B for the Reds and immediately made an impact hitting 17 home runs and stealing 25 bases. In his second season with the Reds he became a 30-30 guy hitting 30 home runs and stealing 32 bases in route to finishing 22nd in the National League MVP voting. Through 2015, Phillips has made three All-Star teams, won four Gold Gloves, and won a Silver Slugger as a member of the Reds. Whether his manager told him he couldn’t work with Phillips or not, Shapiro’s willingness to go along with the move was definitely a poor decision.
Next: #2: Trading Archer for DeRosa