MLB Free Agency: 5 Players the Chicago Cubs Regretted Losing in Free Agency

Joel Reuter@JoelReuterBRFeatured ColumnistOctober 31, 2011

MLB Free Agency: 5 Players the Chicago Cubs Regretted Losing in Free Agency

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    The offseason is here, and it will be a winter of big decisions for new Cubs front-office minds Theo Epstein and Jed Hoyer as they look to take the first step toward turning things around in Chicago.

    One of the biggest decisions that will need to be made this coming season will be whether or not to bring Aramis Ramirez back to play third base, as he has flipped back and forth between saying he will test the market and saying he would like to be back.

    Should they let him walk, it could mean a significant drop in offensive production moving forward as there is no one on the market or in the farm system capable of replacing his production at third base for the 2012 season.

    So here is a quick look back at some free agents that the Cubs decided to let walk in the past, only to regret it down the line when they enjoyed success elsewhere.

Steve Stone

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    Pitching for three different teams with the last being the Cubs, Stone was an average starter at best over the first seven years of his career going 40-48 with a 3.94 ERA. His best season in Chicago came in 1975 when he went 12-8 with a 3.95 ERA.

    Once he left the Cubs though, he enjoyed much more success going 63-38 over his next four seasons pitching for the White Sox and Orioles.

    His 1980 season alone was reason enough that the Cubs would have been wise to hold onto him as he went 25-7, 3.23 ERA, 149 Ks to take home the AL Cy Young.

Rick Reuschel

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    A third-round pick by the Cubs in 1970, Reuschel spent the first nine and a half seasons of his career in Chicago before being dealt to the Yankees at midseason in 1981.

    He was back by 1983 though and would spend two more seasons with the team before finally leaving for good in 1985 at the age of 36 as he looked to be putting the finishing touches on his career in Pittsburgh. In total he tallied 135 wins as a member of the Cubs with a 3.50 ERA.

    He wasn't done, however, as he would win 75 more games over the next seven seasons before retiring at the age of 42. Between 1988 and 1989 alone he went 36-19 with a 3.04 ERA as a member of the Giants. Reuschel's late career performance was unlikely but certainly would have helped a pitching thin Cubs team.

Bob Tewksbury

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    A 16th-round draft pick by the Yankees, Tewksbury broke into the league with New York in 1986 and had an impressive rookie season going 9-5 with a 3.31 ERA in 20 starts. However, the Yankees dealt him to the Cubs the following season as part of a package to acquire starter Steve Trout.

    Tewksbury appeared in just eight games over the two seasons in he spent in Chicago, spending most of his time with the organization in the minor leagues before he was granted free agency at the age of 27 prior to the 1989 season.

    The Cardinals signed him, and after spending most of 1989 in the minors he joined the rotation full-time for the 1990 season. Over the next five seasons he became one of the Cardinals best starters going 66-46 with a solid 3.49 ERA.

    His best season came in 1992 when he went 16-5 with a 2.16 ERA, making his only All-Star appearance and finishing third in NL Cy Young voting.

Luis Gonzalez

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    After spending the first five and a half seasons of his career with the Astros, Gonzalez was traded to the Cubs along with catcher Scott Servais for Rick Wilkins in June of the 1995 season.

    In his only full season with the team the following year, he was the Cubs' everyday left fielder and put together a respectable line of .271 BA, 15 HR, 79 RBI, 70 R while posting a 3.4 WAR.

    The Cubs let him walk after that season though, as he signed a one-year, $1.4 million deal to rejoin the Astros. From there he went to the Tigers before being traded to the Diamondbacks where he became one of the top run producers in all of baseball.

Greg Maddux

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    When Maddux hit free agency following the 1992 season, there was not a more coveted pitcher in all of baseball than the then 26-year old right-hander.

    In just six full seasons in the Cubs rotation, Maddux had compiled a 95-75 record with a stellar 3.35 ERA, and had quickly become one of the league's best pitchers, and was coming off of a Cy Young season.

    After being strongly pursued by the Yankees, and eventually being offered a five year, $34 million contract, Maddux instead signed with the Braves for five years, $28 million and the chance to win a World Series.

    The Cubs signed free-agent Jose Guzman to a four-year, $14.35 million deal to fill Maddux's spot at the front of the rotation, and while he went 12-10 in his first season with the team injuries struck and he would make just four more starts over the duration of the contract

    Maddux went 20-10 and went on to win 194 games in 11 seasons in Atlanta, capturing three Cy Young's in the process as he established himself as one of the best pitchers in baseball history.