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Cubs: Best and worst free agent signings all-time, by position
Cubs: Right field free agents have seen some big hits and big misses.
Best: Andre Dawson
Hall of Fame right fielder Andre Dawson spent six years as a member of the Cubs and is considered one of the best players in franchise history. “The Hawk” had tremendous power at the plate and a rocket for an arm. Five of his six years in Chicago he made the NL All-Star team, which was especially great in 1990 when the mid-summer classic was played at Wrigley Field. Dawson as a Cub slugged 174 home runs, slashed .285/.327/.507 with a 125 OPS+, .843 OPS and 587 RBI.
Despite being on a losing team he won the 1987 NL MVP award, leading baseball in home runs (49), RBI (137) and the NL in total bases (353). The best part of him signing as a free agent? The Cubs literally handed him a blank contract for him to fill out. Not only the most unique free agent signings in team history but ended up being one of the best. Dawson was elected to Cooperstown in 2010 and despite his plaque showing him wearing an Expos hat, his time with the Cubs is well remembered by baseball fans.
Worst: Milton Bradley
Whether it was his underachieving play or his disgusting attitude, Milton Bradley will be seen by many as one of the worst signings in franchise history, period. Bradley was signed by Jim Hendry prior to the 2009 season on a three-year, $30 million contract. The veteran outfielder was an All Star with the Texas Rangers the year prior, hitting a career-high 22 home runs and leading the AL in OBP (.436), OPS (.999) and OPS+ (162).
From a production standpoint, it made sense, but many were wary about his past attitude problems. Sadly he neither improved his attitude nor played up to expectations. Bradley got into it with his manager, his teammates did not like him and he chased himself out of Chicago after hitting only 12 home runs with an OPS of .775 and 100 OPS+. The numbers are pretty average, not horrible, but he was expected to do a lot more. He was eventually traded to Seattle after the 2009 season for Carlos Silva. Shame he was his own worst enemy because in his prime he was a very good hitter.
Remember when Bradley threw the ball into the stands with two outs? That summed up his Cubs tenure right there.