Trading for Aramis Ramirez: Looking for a bat for the stretch run of the 2003 season, Hendry essentially fleeced the Pittsburgh Pirates when he acquired third baseman Aramis Ramirez and outfielder Kenny Lofton for second baseman Bobby Hill, infielder Jose Hernandez and minor league pitcher Matt Bruback on July 23, 2003. Ramirez and Lofton were vital to the Cubs run to within five out of the World Series. Nine seasons and 236 home runs and counting later, Ramirez has solidified the third base position that had been a revolving door since Ron Santo was traded in 1973.
Trading for Derrek Lee: Soon after their collapse in the 2003 NLCS against the Marlins, Hendry traded for a key player from Florida's run to a World Series title that year in first baseman Derrek Lee. Hendry sent once highly-touted first baseman Hee-Seop Choi and minor league pitcher Mike Nanni for the 28-year-old Lee, who became a productive player and clubhouse leader in his six-plus seasons with the Cubs. His best season came in 2005 when he won a batting title with a .335 average to go along with 46 home runs and 107 RBIs.
Signing Ted Lilly: Signed during the great offseason spending spree of 2006, Lilly lived up to his four-year, $40 million contract. He was 47-34 with a 3.70 ERA in three-plus seasons with the Cubs, including a 17-9 season in 2008.
Trading Todd Hundley: Overpaid and unproductive, Hundley appeared to be unmovable, but Hendry not only found a taker, he got back two useful players in return. On Dec. 4, 2002, Hendry traded Hundley and Chad Hermansen to the Los Angeles Dodgers for first baseman Eric Karros and second baseman Mark Grudzielanek. Both played key roles on the 2003 team that advanced to within five outs of the World Series. Karros batted .286 with 12 home runs and 40 RBIs platooning at first base, and Grudzielanek batted .314 as the everyday second baseman.
Hiring Dusty Baker: Hendry and the Cubs scored the biggest managerial name on the market when they hired Baker, a three-time NL Manager of the Year who had just led the San Francisco Giants to the World Series in 2002. Baker brought his signature toothpicks and wrist bands to Chicago and in his first season led the Cubs to within five outs of their first World Series since 1945. He followed that up with a winning season in 2004 but was fired by Hendry after two losing seasons.
Hiring Lou Piniella: Hendry once again went for the big name when naming Baker's successor, hiring Piniella who had managed 19 seasons with four teams. He became the first manager since Frank Chance in 1907-08 to lead the Cubs to two straight playoffs, but each trip ended in first-round sweeps.
Signing Milton Bradley: After two straight trips to the playoffs resulted in first-round sweeps, the Cubs made acquiring left-handed power a priority. That bat turned out to be the well-traveled Bradley, who made the Cubs his seventh team in nine years when he signed a three-year, $30 million contract on Jan. 9, 2009. The mercurial Bradley was a disaster in his only season with Chicago, batting just .257 with 12 home runs and 40 RBIs before being banished for the rest of the season when he criticized the organization and its fans.
Re-signing Carlos Zambrano: Although it would be hard to find anyone who disagreed with re-signing Zambrano to a five-year, $91.5 million deal in 2007, the move looks like a mistake now. Zambrano's velocity has diminished as has his production. His blowups on the field have made him toxic in the clubhouse, and his big contract and no-trade clause makes him almost impossible to trade.
Signing Kosuke Fukudome: The Cubs outbid the San Diego Padres for the former Japanese League star, signing him to a four-year, $48 million contract before the 2008 season. Fukudome made a splash early, hitting a home run in his Wrigley Field debut and making the All-Star team later that summer, but his production over three-plus seasons never rose above that of a fourth outfielder.
No-trade clauses: Hendry handed out plenty of no-trade clauses during his tenure and many came back to bite him. From Zambrano to Lee to Ramirez, Hendry was hamstrung by the contract concessions. Even draft pick Jeff Samardzija received a no-trade to help convince him to give pick the Cubs over a football career.
Signing Alfonso Soriano: Calling Soriano a miss could be a tough assessment. He was a vital piece of two straight playoff runs, and carried the Cubs during September 2007 with 14 home runs and 27 RBIs during the month. And there were far more supporters of the Cubs signing him to an eight-year, $136 million contract in 2007 than detractors. He has hit 20-plus home runs in each of his five seasons in Chicago but his defense makes him a liability in left field. With over $60 million left on his deal -- which include a no-trade clause -- the Cubs might be stuck with an aging Soriano.