Updated: October 27, 2011 12:32AM
• Acquired Aramis Ramirez, Kenny Lofton and cash from the Pittsburgh Pirates for Jose Hernandez, Bobby Hill and minor-leaguer Matt Bruback on Aug. 15, 2003, helping put the Cubs over the top in the playoff race and stabilizing third base for the first time in 30 years.
• Acquired Derrek Lee from the Florida Marlins for Hee-Seop Choi and minor-leaguer Mike Nanni before the 2004 season, landing a middle-order hitter and Gold Glove first-baseman who lasted seven seasons (including two playoff years) in Chicago.
• Hired respected scouting executive Tim Wilken away from Tampa Bay before the 2006 season to run the scouting department and draft, a move that has corresponded with the Cubs’ recent run of homegrown big-league position players.
• Gambled and lost on the $30 million free-agent signing of Milton Bradley before the 2009 season, made worse by depth-killing trade of Mark DeRosa to free payroll for the signing (and by the subsequent signing of Aaron Miles to replace DeRosa).
• “Won’’ a four-team bidding war before the 2008 season to overpay former Japanese batting champion Kosuke Fukudome (below) with a four-year, $48 million contract.
• Waived third baseman Casey McGehee after the 2008 season. Division-rival Milwaukee claimed McGehee, who then averaged .291, 20 homers and 85 RBI the last two years in his first two full seasons in the big leagues.
NOTE: Alfonso Soriano’s eight-year, $136 million deal was not considered for this list because that deal was personally escalated and closed by former Cubs president John McDonough.