Here are the 13 best trades in Cubs franchise history
Honorable mention: Milton Bradley to Mariners (2009)
Cubs receive: SP Carlos Silva, $9 million in cash
Mariners receives: RF Milton Bradley
I recently named Bradley as the worst free agent signing in team history. The Cubs signed the mercurial outfielder ahead of the 2009 season, and his numbers dropped dramatically from 2008. He criticized the Cubs in September 2009 in a newspaper interview, getting suspended for the rest of the season after.
Silva had a rough second half in 2010 but posted a 3.45 ERA in 17 first half outings. Ultimately, the Cubs traded a controversial player, and rather than paying for him to go away, got paid (to cover Silva's contract). Pretty solid move.
13. Aroldis Chapman from Yankees (2016)
Cubs receive: CL Aroldis Chapman
Yankees receive: P Adam Warren, OF Billy McKinney, OF Rashad Crawford, SS Gleyber Torres
Chapman came up huge multiple times in the 2016 postseason, tossing 2 2/3 innings in Game 5 of the World Series and 1 1/3 in both Games 6 and 7. Fans mostly remember Rajai Davis banging a two-run blast of him in Game 7 to knot the score at 6, but Chapman shut Cleveland down in the ninth, leading to the Cubs taking the lead for good in the tenth.
Torres has emerged into a superstar-in-the-making in New York, but the Cubs knew this was a possibility when trading him. Chapman was worth the cost, as there may not be a championship without him.
12. Dexter Fowler from the Astros (2015)
Cubs receive: CF Dexter Fowler
Astros receive: INF Luis Valbuena, P Dan Straily
The Cubs acquired a key cog to their championship team for a hitter coming off a career year and a swingman. Fowler was a catalyst for the Cubs offense in 2015-16, hitting .261/.367/.427 while serving as the leadoff man.
Fowler was a starter in the 2016 All-Star game, and the Cubs went 46-13 in 2016 when he got on base to leadoff a game. The Cubs' worst stretch that season came when Fowler missed a month with a hamstring injury.
He also hit the first ever leadoff home run in a World Series Game 7, kick-starting the Cubs championship-clinching win.
11. Derrek Lee from Marlins (2003)
Cubs receive: 1B Derrek Lee
Marlins receive: 1B Hee-Seop Choi, P Mike Nannini
Following their 2003 championship, the Marlins conducted a mass sell-off to save money, and the Cubs happily took Lee off their hands.
Lee — who helped the Marlins beat the Cubs in that infamous 2003 NLCS — spent six and a half seasons in Chicago, slashing .298/.378/.524 with 179 homers. He made two All-Star games, won two Gold Gloves and a Silver Slugger. He was in the mix for the 2005 NL Triple Crown.
Choi, an average hitter, played two more big league seasons before returning to South Korea, where he played through 2015. Coincidentally, Lee’s dad — Leon — scouted and signed Choi for the Cubs.
10. Kyle Hendricks from Rangers (2012)
Cubs receive: SP Kyle Hendricks, 3B Christian Villanueva
Rangers receive: SP Ryan Dempster
After a trade with the Braves fell through, Theo Epstein pivoted to the Rangers shortly before the deadline, viewed as a lesser deal at the time. Not anymore.
Hendricks’ 3.14 ERA since 2014 is tied for No. 14 in baseball. He won MLB’s ERA title in 2016, later outpitching Clayton Kershaw in the pennant-clinching game. He started Game 7 of the World Series, allowing an earned run in 4 2/3 innings before Joe Maddon shockingly pulled him.
Hendricks is the Cubs’ most steady starter and Dempster retired in 2014. The Cubs eventually non-tendered Villanueva.
9. Rick Sutcliffe from Indians (1984)
Cubs receive: SP Rick Sutcliffe, RP George Frazier, C Ron Hassey
Indians receive: OF Mel Hall, OF Joe Carter, SP Don Schulze, SP Darryl Banks
Acquiring Sutcliffe helped push the Cubs back into the postseason for the first time since 1945. The Red Baron, in the midst of a rough year with Cleveland (5.15 ERA, 15 starts), went on a torrid run with the Cubs. In 20 starts, he went 16-1 with a 2.69 ERA, winning the NL Cy Young Award despite spending a chunk of the season in the AL.
The Cubs came a game shy of the World Series, blowing a 2-0 series lead in the NLCS. Sutcliffe spent seven more seasons in Chicago, posting a 3.74 ERA in 193 outings — all but three as a starter.
8. Mordecai Brown from Cardinals (1903)
Cubs receive: SP Moredecai Brown, C Jack O’Neill
Cardinals receive: SP Jack Taylor, C Larry McLean
The dead ball era was extremely pitcher friendly, but Brown put up some video game numbers in 10 seasons with the Cubs. “Three Finger’ sported a 1.80 ERA in 346 games (241 starts) with a pristine 0.998 WHIP. He tossed 48 shutouts, 13 ahead of Hippo Vaughn for most in franchise history.
The Cubs won four pennants during Brown’s tenure, winning back-to-back World Series (1907-08).
Taylor pitched two and a half seasons with St. Louis before returning to the Cubs in 1906. McLean left St. Louis after the 1904 season.
7. Anthony Rizzo from Padres (2012)
One of the more lopsided trades on this list. After marketing Cashner as one of the faces of their future in 2011, the Cubs traded him for the eventual face of the franchise.
Rizzo is one of the best all-around first baseman in baseball, a leader in the clubhouse and an exemplary person off the field. In eight seasons as a Cub, he's hit .277/.376/.496 with 217 home runs. He’s made three All-Star teams, won three Gold Gloves, finished in the top 4 of MVP voting twice and led the Cubs to a championship.
Cashner spent four and a half seasons with the Padres posting a 3.67 ERA in 130 outings (97 starts). Not bad, but the Cubs would do this trade every time.
6. Kiki Cuyler from Pirates (1927)
Cubs receive: OF Kiki Cuyler
Pirates receive: INF Sparky Adams, OF Pete Scott
Another lopsided deal. Cuyler finished second in the NL MVP voting in 1925, and the Cubs got him for Adams (who left Pittsburgh after 1929) and Scott (whose career ended after 1928).
Cuyler spent seven and a half seasons on the North Side, hitting .325/.391/.485 while scoring 155 runs in 156 games in 1930. He helped Chicago win pennants in 1929 and 1932 and was elected into the Hall of Fame in 1968, properly donning a Cubs cap.
5. Sammy Sosa from White Sox (1992)
Cubs receive: RF Sammy Sosa
White Sox receive: P Ken Patterson, LF George Bell
Steroids or no steroids, this trade has to be near the top of this list. Sosa hit 545 of his 609 career home runs with the Cubs. He won the NL MVP award in 1998, when he hit 66 home runs — still the Cubs' franchise record for a single season. He made seven All-Star teams and earned six Silver Slugger awards.
Sosa’s been estranged from the Cubs for more than a decade, and his tenure ended on a sour note — he left the team’s final game in 2004 shortly after first pitch.
Regardless, he’s one of the best players in team history, and the 1998 home run race vs. Mark McGwire produced one of the most exciting summers in baseball history.
4. Aramis Ramirez and Kenny Lofton from Pirates (2003)
Cubs receive: 3B Aramis Ramirez, CF Kenny Lofton
Pirates receive: INF José Hernández, P Matt Bruback, 2B Bobby Hill
The Cubs capitalized on Pittsburgh’s desire to shed payroll, adding two key lineup pieces for their eventual run to the NLCS. Lofton settled in as the Cubs leadoff man, hitting .327 with a .381 OBP in 56 games.
Ramirez spent eight and a half seasons with the Cubs and was a fixture in the middle of the order. He hit .294/.356/.531 and is sixth on the club’s all-time home run list (239). He made two All-Star teams.
For who they gave up, Pittsburgh acquiring three players who didn’t make much of a mark is astonishing.
3. Fergie Jenkins from Phillies (1966)
Cubs receive: SP Fergie Jenkins, CF Adolfo Phillips, 1B/OF John Herrnstein
Phillies receive: SP Larry Jackson, SP Bob Buhl
It’s hard not putting one of the best pitchers in Cubs history higher on this list. Jenkins pitched for the Cubs from 1966-73 and 1982-83, posting a 3.20 ERA and 1.123 WHIP. He threw 154 complete games (29 shutouts), made three All-Star games, won a Cy Young Award and finished in the top 3 of voting four other times.
Jackson posted a 2.95 ERA in parts of three seasons with Philly; Buhl posted a 4.93 in two and retired after 1967.
Jenkins was elected to the Hall of Fame in 1991. The Cubs retired his No. 31 alongside Greg Maddux in 2009.
2. Jake Arrieta and Pedro Strop from Orioles (2013)
Cubs receive: SP Jake Arrieta, RP Pedro Strop
Orioles receive: SP Scott Feldman, C Steve Clevenger
There’s a case to be made this is No. 1. Feldman had a nice half season with the Cubs (3.46 ERA, 15 starts) but Arrieta and Strop became North Side mainstays.
Arrieta never put it together in Baltimore (5.46 ERA, four seasons) but evolved into the Cubs’ ace and eventual Cy Young winner. His 2015 second half was one for the ages: 15 starts, 0.75 ERA, 0.727 WHIP. In total, he posted a 2.73 ERA and 1.034 WHIP in five seasons — plus a 3.08 ERA and 1.082 WHIP in nine postseason starts.
Strop will go down as one of the best Cubs relievers ever. He posted a 2.90 ERA and 1.048 WHIP from 2013-19. He made 411 career appearances, No. 6 in franchise history. His 120 holds are most in franchise history, and it’s not even close. (Carlos Marmol is second with 83.)
1. Ryne Sandberg from Phillies (1982)
Cubs acquire: 2B Ryne Sandberg, SS Larry Bowa
Phillies acquire: SS Ivan de Jesus
Sandberg was considered a throw-in for this deal because Bowa wanted out of Philadelphia. That's funny, looking back on it. Bowa had an unproductive Cubs tenure across four seasons, and de Jesus spent three mediocre years in Philadelphia.
Sandberg played 15 seasons in Chicago (1982-94, 1996-97), hitting .285/.344/.452 with 282 home runs (No. 5 in Cubs history). He made 10 All-Star teams, won nine Gold Gloves, seven Silver Sluggers and the 1984 NL MVP award. He was inducted into the Hall of Fame in 2005 and is one of the best Cubs of all-time.