Chicago had a 1 1/2-game lead and the rotation was dealing with injuries when it made the deal for Sutcliffe, who was 4-5 with a 5.15 ERA at that point with Cleveland. The right-hander finished the year 16-1 with a 2.69 ERA, won the National League Cy Young Award and helped the Cubs get to the playoffs for the first time since 1945.
Some say the Cubs gave away more than they got -- dealing future World Series hero Joe Carter for Sutcliffe, who battled injuries. Sutcliffe also won 18 games in 1987, 13 in '88 and 16 in '89 with the Cubs. Hassey played 14 seasons in the big leagues, while Banks and Schulze never made it.
2. April 21, 1966: Cubs receive right-handed pitcher Ferguson Jenkins, outfielder Adolfo Phillips and outfielder/first baseman John Herrnstein from the Phillies for right-handers Larry Jackson and Bob Buhl.
The deal was made nine days after the season began. Chicago was desperate for pitching help and picked up Jenkins, who was 22 years old at the time. The right-hander posted six straight 20-win seasons and compiled a 167-132 record and 3.20 ERA in 10 seasons with the Cubs. He finished with 997 walks in 664 games.
Phillips delivered three productive seasons before he was dealt to the Expos. Buhl and Jackson combined for a 47-53 mark with the Phillies, then retired. Jenkins, who also pitched for the Rangers and Red Sox, finished with 284 wins and secured a spot in Cooperstown in 1991.
3. July 23, 2003: Cubs receive third baseman Aramis Ramirez, outfielder Kenny Lofton and cash from the Pirates for infielder Jose Hernandez, Minor League right-handed pitcher Matt Bruback and a player to be named. Second baseman Bobby Hill was sent to the Pirates to complete the deal.
Chicago was counting on young Corey Patterson to lead off and cover center, and he batted .298 in 83 games but suffered a knee injury on July 6, 2003. Lofton filled the leadoff spot, batting .327 in 56 games, while Ramirez was Mr. Clutch, hitting 15 home runs and driving in 39 runs in 63 games. Lofton and Ramirez -- plus the late addition that year of first baseman Randall Simon, acquired Aug. 17 -- gave the Cubs the offensive spark they needed to reach the playoffs.
A solid defensive player, Ramirez stayed with Chicago for nine seasons, totaling 239 home runs and 806 RBIs. Hernandez was versatile and popular, but he was batting .188 at the time with the Cubs. He lasted 15 seasons in the big leagues, playing for nine different teams.
4. June 15, 1949: Cubs receive outfielders Hank Sauer and Frankie Baumholtz from the Reds for outfielder Harry Walker and outfielder/third baseman Peanuts Lowrey.
Walker was the 1947 batting champion and ended up playing 165 games for Cincinnati before retiring. Sauer was 32 at the time of the trade and had his best years ahead of him. He batted .367 in his first 39 games with the Cubs; he added 15 home runs and 45 RBIs. Sauer belted 171 homers with the Cubs, drove in 100 runs three times, and won the NL Most Valuable Player Award in 1952. Baumholtz, a throw-in in the deal, developed into a solid center fielder and batted over .300 for five seasons with the Cubs.
5. Aug. 13, 1913: Cubs receive left-hander Hippo Vaughn from the Kansas City Minor League team for right-hander Lew Richie.
The Yankees weren't high on Vaughn after a 2-8 season in 1912, and the Senators claimed him on waivers. The Cubs found Vaughn in the Minors, and he became the best left-handed starter in team history, totaling 151 wins, 35 shutouts and five 20-win seasons. Vaughn still holds team marks for most wins by a lefty, most starts (270), most complete games (177), most shutouts, most innings pitched (2,216 1/3) and most strikeouts (1,138).