10 biggest trades in Cubs history

November 22nd, 2018

Across baseball, perhaps no transaction sparks more fan and media debate than the trade. And with nearly a century and a half of baseball played on the north side of Chicago, there might be no place richer with examples of deals gone good and bad, hits and misses, some shaping the franchise for years to come.

Which worked? Which didn't? With this as a backdrop, MLB.com is taking a look back. Here are the 10 trades that made the biggest impact on the Cubs' long and storied history.

1. Bowa for de Jesus, with a famous throw-in

Cubs got from Phillies: 2B Ryne Sandberg, SS Larry Bowa

Cubs gave up: SS Ivan de Jesus

Date: Jan. 27, 1982

Ryne Sandberg was a 21-year-old, former 20th-round Draft pick with 13 games of big league experience when the Cubs sent the useful but unspectacular de Jesus to Philadelphia for him and Bowa in 1982, at which point Chicago was in the midst of a 37-year postseason drought. Bowa was the headliner here, and he contributed regularly for three seasons. But it was Sandberg who became a star, won National League MVP Award honors while helping snap that drought two years later, and turned into arguably the best second baseman in club history. He anchored the Cubs infield for 15 seasons and was inducted to the Hall of Fame in 2005.

2. Fergy to the Friendly Confines

Cubs got from Phillies:
RHP Ferguson Jenkins, OF Adolfo Phillips, 1B John Herrnstein

Cubs gave up: RHP Larry Jackson, RHP Bob Buhl

Date: April 21, 1966

Jenkins showed promise as a rookie in 1966 with the Phillies, but Philadelphia surely didn't expect him to blossom like he did in Chicago. If they had, the Phillies certainly wouldn't have shipped away Jenkins for five combined seasons of Jackson and Buhl, who were both out of baseball by the time Jenkins captured the NL Cy Young Award in 1971. That was his fifth of eventual six consecutive 20-win seasons Jenkins would rattle off in Chicago, where he spent 10 of his 19-year Hall of Fame career.

3. Sutcliffe, second-half savior

Cubs got from Indians:
RHP Rick Sutcliffe, RHP George Frazier, C Ron Hassey

Cubs gave up: OF Joe Carter, OF Mel Hall, RHP Don Schulze, RHP Darryl Banks

Date: June 13, 1984

One of the most famous midseason deals in baseball history, and one that worked for both sides. The Cubs got everything they needed in Sutcliffe, who went 16-1 with a 2.69 ERA after the trade to grab the NL Cy Young Award and power Chicago into the postseason. The right-hander spent seven more seasons on the North Side, making two All-Star teams. But getting Sutcliffe required the Cubs to part with a bundle headlined by a top prospect named Joe Carter, who went on to have a pretty nice career and make some significant postseason memories of his own.

4. Sammy from the South Side

Cubs got from White Sox: OF Sammy Sosa, LHP Ken Patterson

Cubs gave up: OF George Bell

Date: March 30, 1992

One year after signing Bell in free agency, the Cubs sent the former MVP across town for an inauspicious package: a career reliever and Sosa, who'd hit just 28 home runs in 302 games over three seasons for the White Sox. Then Sosa became Slammin' Sammy.

Sosa grew into a legit run producer over his first five seasons with the Cubs, but nothing prepared Chicago for what was to come. Sosa hit 292 home runs and drove in 705 runs from 1998-2002 -- capturing two home run titles, an MVP and becoming one of the sport's main attractions in the process. He ended up hitting 545 home runs across 13 years on the North Side and remains perhaps the most exciting player in club history, even if his legacy is muddled by the corked bat incident of '03 and suspicion of performance enhancing drug use, which has crippled his Hall of Fame chances.

5. Three-Finger Brown comes to town

Cubs got from Cardinals: RHP Mordecai Brown, C Jack O'Neill

Cubs gave up: C Larry McLean, RHP Jack Taylor

Date: Dec. 12, 1903

The Cubs needed to unload Taylor after he accused team president James Hart for throwing games, leading to one of the 20th century's first blockbusters -- a deal that netted Chicago one of the premier Deadball Era aces in Brown. Also known as "Three-Finger," Brown took advantage of a pitching hand mangled by a childhood accident with farming machinery to throw a unique curveball that baffled hitters.

The future Hall of Famer helped lead the Cubs to four pennants in five years, including two World Series titles in 1907-08, and finished with a .691 win percentage and 1.75 ERA over his first nine-year tenure in Chicago. Taylor went just 43-49 in three seasons with St. Louis before returning to the Cubs.

5. Brock for Broglio

Cubs got from Cardinals: RHP Ernie Broglio, OF Doug Clemens, LHP Bobby Shantz

Cubs gave up: OF Lou Brock, RHP Paul Toth, LHP Jack Spring

Date: June 15, 1964

Lopsided for the wrong reasons from the Chicago perspective, this trade still lands a spot on this list for its significance: It is considered among the biggest heist in baseball history. By now, the specifics are well documented. Though a former win champion and coming off a productive season, Broglio sputtered in Chicago and was out of baseball by age 30. Brock, meanwhile, found his feet in St. Louis, immediately led the Cardinals to a World Series title, and blossomed into one of the most dynamic players ever. The deal will resonate in the storied Cubs-Cardinals rivalry for as long as there is one.

7. The Arrieta trade

Cubs got from Orioles: RHP , RHP

Cubs gave up: RHP , C Steve Clevenger

Date: July 2, 2013

A failed prospect in Baltimore, Arrieta was shipped to Chicago with the Orioles eying a playoff push and Feldman working on his best season in years. His became a classic reclamation story: Arrieta emerged as one of the most dominant starters in baseball, won the 2015 NL Cy Young Award and went 64-29 with a 2.67 ERA across parts of five seasons in Chicago. Feldman regressed in Baltimore, the Orioles missed the playoffs, and the righty bounced between three teams over the next five years before calling it a career.

8. Riz for Cash

Cubs got from Padres: 1B

Cubs gave up: RHP

Date: Jan. 6, 2012

As the executive who drafted Rizzo in Boston, Theo Epstein knew the player he was getting when he acquired the first baseman in what looked like an even swap for highly touted prospects at the time. So did GM Jed Hoyer, who developed Rizzo in the Padres farm system. That prior knowledge ended up making what amounted to their first major trade in Chicago a lopsided one.

Rizzo turned into an All-Star slugger and centerpiece of the Cubs' 2016 World champion team, while Cashner never put it together in San Diego and put up below-league average production throughout his career.

9. The Kiki Cuyler coup

Cubs got from Pirates: OF Kiki Cuyler

Cubs gave up: INF Sparky Adams, OF Pete Scott

Date: Nov. 28, 1927

The speedy Cuyler was already a star when the Cubs snagged him from the Pirates for Adams, a similar-style but inferior player. So why did Pittsburgh send Cuyler away? It had nothing to do with his play. The future Hall of Famer repeatedly clashed with Pirates manager Donie Bush, so much so that he sat out the entire 1927 World Series before management cut its losses. The Cubs were the beneficiaries: Cuyler won three stolen bases titles from 1928-30, and hit .325 while notching three 200-hit seasons across the eight years he'd spend on the North Side.

10. A good deal for Aramis

Cubs got from Pirates:
3B Aramis Ramirez, CF Kenny Lofton, cash

Cubs gave up: INF Jose Hernandez, RHP Matt Bruback, INF Bobby Hill

Date: July 23, 2003

The Cubs had a glaring need at third base at the time, but it was an injury to young center fielder Corey Patterson that paved the way for this deal, perhaps the best of Jim Hendry's tenure as GM. Patterson's injury made Lofton, an aging veteran on an expiring contract with the non-contending Pirates, a fit. And he was sensational down the stretch, hitting .327 with 12 stolen bases to help propel the Cubs to the postseason.

But it was Ramirez who gave the deal lasting impact. In hindsight, the Pirates were shortsighted: Ramirez rebounded from the sophomore slump he suffered through in 2002 to become one of the most productive offensive players in Cubs history, hitting .294/.256/.531 with 239 home runs and 806 RBI across nine seasons manning the hot corner.