10 biggest trades in Cubs history

December 1st, 2021

Hall of Famers. Prolific home run hitters. Critical pieces to World Series champions. Each of those descriptions fit players who were added via trade throughout the Cubs' long and storied history.

With such a wealth of history, it is a daunting task to try to identify the best trades in the club's many seasons. When famous acquisitions such as Pete Alexander and Gary Matthews are among those that did not make the cut, you know the list is lengthy. Fans undoubtedly have opinions on the deals that did not work out in Chicago's favor. (Lou Brock says hello.)

This exercise is about the swaps that did pay dividends for the North Siders. With that in mind, here are our Top 10 trades in Cubs history:

1. Reeling in Ryno
Cubs got from Phillies: SS Larry Bowa, 2B Ryne Sandberg
Cubs gave up: SS Ivan de Jesus
Date: Jan. 27, 1982

Sandberg was considered a throw-in part of this trade, but he finished his career as one of the greatest second basemen in MLB history. Over 15 seasons with the Cubs, Sandberg amassed 282 homers, 403 doubles and 2,385 hits. The Hall of Famer was a seven-time Silver Slugger Award winner, nine-time Gold Glove Award recipient, 10-time All-Star and took home the National League Most Valuable Player Award in 1984. The Phillies, meanwhile, got three underwhelming seasons out of de Jesus.

2. Bell for Sosa
Cubs got from White Sox: LHP Ken Patterson, OF Sammy Sosa
Cubs gave up: OF George Bell
Date: March 30, 1992

The White Sox swung this trade for Bell with the idea of utilizing the veteran slugger -- coming off a strong 1991 tour with the Cubs -- as a designated hitter. The crosstown deal sent a raw talent in Sosa to the Cubs, who watched him turn into one of the game's all-time great power hitters. Sosa belted 545 of his 609 career homers on the North Side, where he made seven All-Star teams and won the NL MVP in '98. That summer, Sosa and Cardinals slugger Mark McGwire captivated the baseball world while chasing down Rogers Maris' previous single-season homer mark of 61 in '61.

3. Finding Fergie
Cubs got from Phillies: OF John Herrnstein, RHP Ferguson Jenkins, OF Adolfo Phillips
Cubs gave up: RHP Bob Buhl, RHP Larry Jackson
Date: April 21, 1966

Jenkins showed promise in his debut with the Phillies, but he blossomed when the Cubs landed the righty and put him in their rotation. He spent parts of 10 seasons with Chicago, piling up 167 wins with a 3.20 ERA with the North Siders. Along the way, he made three All-Star teams and finished in the top three in NL Cy Young Award voting four times, including winning the award in 1971. Jenkins was enshrined in the Hall of Fame in '91. For Philadelphia, Jackson was most noteworthy, posting a 2.95 ERA over 752 1/3 innings over parts of three seasons.

4. Adding Three Finger
Cubs got from Cardinals: RHP Mordecai Brown, C Jack O'Neill
Cubs gave up: C Larry McLean, RHP Jack Taylor
Date: Dec. 12, 1903

"Three Finger" Brown spent 10 of his 14 seasons with Chicago, during which he fashioned a 1.80 ERA. Statistics from that early era look much different than today, but it is still remarkable to see 48 shutouts and 206 complete games over 2,329 innings with Chicago. The Hall of Famer also played a key role in the Cubs' back-to-back World Series triumphs over Detroit in 1907-08, giving up no runs over 20 innings. On the other side of the coin, Taylor was brilliant for St. Louis in 1904 (2.22 ERA in 352 innings), but his career was done by '08.

5. Baltimore swap
Cubs got from Orioles: RHP , RHP and international bonus cash
Cubs gave up: RHP , C Steve Clevenger
Date: July 2, 2013

This wound up being a flop for the Orioles, who only got an underwhelming half-season out of Feldman and nothing to write home about from Clevenger over a few Major League tours. Arrieta, on the other hand, blossomed into a frontline starter and Strop a bullpen fixture with the Cubs. Arrieta went 68-31 with a 2.73 ERA in parts of five seasons with Chicago, winning the 2015 NL Cy Young Award with a 22-6 ledger and 1.77 ERA. In '16, he went 2-0 with a 2.38 ERA in two World Series starts to help lead the Cubs to their first championship since 1908.

6. Acquiring Kiki
Cubs got from Pirates: OF Kiki Cuyler
Cubs gave up: INF Sparky Adams, OF Pete Scott
Date: Nov. 27, 1927

The Cubs netted Cuyler in the prime of his Hall of Fame career, which included playing in the 1929 and '32 World Series with Chicago. Cuyler was with the Cubs for eight of his 18 seasons, in which he hit .321 with 128 homers, 157 triples, 328 steals, 394 doubles, 1,304 runs scored and an .860 OPS. He scored 155 runs in 156 games in '30 and was an All-Star with the Cubs in '34. Combined, Pittsburgh only received three years of production between Adams and Scott.

7. The Red Baron
Cubs got from Indians: RHP George Frazier, C Ron Hassey, RHP Rick Sutcliffe
Cubs gave up: RHP Darryl Banks, OF Joe Carter, OF Mel Hall, RHP Don Schultze
Date: June 13, 1984

Cleveland netted six productive seasons out of Carter (126 steals, 151 homers and 530 RBIs) and eventually flipped him to the Padres in '89 to land catcher Sandy Alomar and second baseman Carlos Baerga. The Cubs' acquisition of Sutcliffe, however, produced one of the great Cy Young stories in history. After posting a 5.15 ERA for the Indians to start the '84 campaign, Sutcliffe went 16-1 with a 2.69 ERA down the stretch after joining the Cubs. That showing helped the righty win the NL Cy Young Award that year, in which he helped Chicago reach the NL Championship Series. Over eight years with the Cubs, the Red Baron went 83-65 with a 3.74 ERA.

8. Raiding the Pirates
Cubs got from Pirates: OF Kenny Lofton, 3B Aramis Ramirez
Cubs gave up: RHP Matt Bruback, INF Jose Hernandez, INF Bobby Hill
Date: July 23, 2003

Third base had been a turnstile for the Cubs for decades prior to Ramirez's arrival in the '03 trade with Pittsburgh. The deal helped fortify Chicago's roster for the '03 run to the NLCS, but it also gave the franchise an eight-time Opening Day third baseman. Over parts of nine seasons with the Cubs, Ramirez hit .294 with 239 homers and an .887 OPS, earning two All-Star nods and one Silver Slugger along the way. None of the players on the Pittsburgh side of the deal panned out.

9. Landing Rizzo
Cubs got from Padres: RHP Zach Cates, 1B
Cubs gave up: RHP , OF Kyung-Min Na
Date: Jan. 6, 2012

Cashner went 28-43 with a 3.67 ERA in five seasons with San Diego, hardly living up to the kind of return that would have made this trade less lopsided. Rizzo joined the Cubs and soon became a fan favorite, earning a place on multiple All-Star teams, turning in Gold Glove-caliber defense and becoming a lock for 30-homer, 100-RBI seasons. Rizzo joined a young Cubs core that helped end the franchise's 100-plus year World Series drought with the '16 victory over Cleveland.

10. The Derrek deal
Cubs got from Marlins: 1B Derrek Lee
Cubs gave up: 1B Hee-Seop Choi, RHP Mike Nannini
Date: Nov. 24, 2003

The Cubs turned the page on the Choi era with this trade, which brought in an impact bat and defender in Lee. Over parts of eight seasons with Chicago, Lee hit .294 with 179 homers, 574 RBIs and a .903 OPS. He made two All-Star teams, won two Gold Gloves and finished third in NL MVP voting in 2005. For the Marlins, Choi only lasted part of one season, while Nannini never reached the Majors.