During his time as general manager, Hendry was responsible for several high-profile trades and signings that shaped the Cubs' roster. One of his first major moves was acquiring Aramis Ramirez and Kenny Lofton from the Pittsburgh Pirates in 2003, a trade that significantly bolstered the team's lineup. That same year, the Cubs reached the National League Championship Series, coming within one game of the World Series.
Hendry's tenure was marked by a mix of successes and challenges. In 2007 and 2008, the Cubs won back-to-back National League Central Division titles, a feat that had not been accomplished by the team since the early 1900s. These achievements were partly due to Hendry's efforts in assembling a competitive roster, including the signing of key players like Alfonso Soriano and Ted Lilly.
However, Hendry also faced criticism for some of his decisions, particularly long-term contracts that did not pan out as expected. The team's performance declined after the 2008 season, and the Cubs struggled to maintain their competitive edge. Despite these challenges, Hendry remained committed to improving the team, making various trades and signings in an attempt to return the Cubs to postseason contention.
In August 2011, Hendry was relieved of his duties as general manager. His departure marked the end of an era for the Cubs, as the organization sought new leadership to guide the team forward. Hendry's legacy with the Cubs is a complex one, characterized by moments of triumph and periods of difficulty.
After leaving the Cubs, Hendry continued his career in baseball, taking on a role as a special assistant to the general manager with the New York Yankees. His experience and knowledge of the game have kept him involved in the sport, contributing to various teams in different capacities.
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