Here are the 9 worst trades in Cubs franchise history
9. Jon Garland to White Sox (1998)
Cubs receive: RP Matt Karchner
White Sox receive: SP Jon Garland
The Cubs, holding a wild-card position, sought to bolster their bullpen ahead of closer Rod Beck. Karchner started 1998 as the White Sox closer, but he held a 5.15 ERA (4.18 FIP) and 1.418 WHIP at the time of the trade.
The Cubs ultimately made the postseason, but Karchner wasn’t any better on the North Side (5.14 ERA, 6.13 FIP, 1.389 WHIP). He last pitched in 2000, while Garland — the No. 10 overall pick in 1997 — went on to have a 13-year career. He won 18 games in both 2005 and ’06, helping the White Sox win the World Series in the former.
8. Eloy Jimenez and Dylan Cease to White Sox (2017)
Cubs receive: SP José Quintana
White Sox receive: OF Eloy Jimenez, SP Dylan Cease, 1B Matt Rose, INF Bryant Flete
The Cubs were looking to acquire a cost-controlled starter. They did that, getting Quintana and his team-friendly contract. He posted a 3.74 ERA with the Cubs in 2017, and without him, they may have missed the postseason a year after winning the World Series.
Quintana has been inconsistent the past two seasons, not what the Cubs envisioned when they surrendered their top two prospects. Jimenez hit 31 home runs as a rookie last season, and while Cease struggled, there’s still a ton of promise there. Had the Cubs kept the two, maybe they would have traded one or both of them later for a more valuable return.
This wasn’t a good deal, but it hasn’t been a complete flop (ducks). In a few years, however, this could go down as an all-timer.
7. Rafael Palmeiro and Jamie Moyer to Rangers (1988)
Cubs receive: CL Mitch Williams, P Paul Kilgus, P Steve Wilson, INF Curt Wilkerson, INF Luis Benitez, OF Pablo Delgado
Rangers receive: LF Rafael Palmeiro, P Jamie Moyer, P Drew Hall
You don’t see many nine-player trades these days. Cubs general manager Jim Frey desperately wanted a closer (more on that in a bit) and getting one (Williams) cost him one of the club’s most promising young players in Palmeiro.
Palmeiro hit .307 in 1988, second best in the National League. He went on to hit 569 career home runs, while Moyer pitched until he was 49 in 2012. Williams spent two seasons in Chicago, making the All-Star team in 1989 before leaving for the Phillies in 1991.
Even with Palmeiro’s eventual connection to steroids — he was suspended for a positive test in 2005 — this trade isn’t remembered kindly.
6. Josh Donaldson to A’s (2008)
Cubs receive: SP Rich Harden, RP Chad Gaudin
A’s receive: SP Sean Gallagher, OF Matt Murton, OF Eric Patterson, C Josh Donaldson
The Cubs added Harden to match the Brewers’ acquisition of CC Sabathia. In 12 starts with the Cubs that season, the oft-injured right-hander sported a 1.77 ERA (3.08 FIP) and 0.972 WHIP. He wasn’t nearly as good in 2009 (4.09 ERA, 4.35 FIP, 1.340 WHIP) and departed as a free agent in the offseason.
Donaldson was only a Single-A catcher at the time and was hitting .217/.276/.349 leading up to the deal. Now, he’s a three-time All-Star and one-time MVP, holding a career .273/.369/.509 line with 219 home runs in nine big league seasons.
Surrendering Donaldson may warrant including this trade in the top five, but the Cubs got some value out of Harden, at least.
5. DJ LeMahieu to Rockies (2011)
Cubs receive: 3B Ian Stewart, RP Casey Weathers
Rockies receive: OF Tyler Colvin, 2B DJ LeMahieu
No sugarcoating this one — it was a bad trade. Stewart was meant to replace Aramis Ramirez, who left for the Brewers in free agency, at third base. He played in 55 games in 2012, hitting .201/.292/.335 with five homers and 17 RBIs before undergoing season-ending wrist surgery in July.
Stewart spent 2013 in the minor leagues, and that June he tweeted the Cubs were letting him “rot” and “might as well release me.” Two weeks later, they did.
Theo Epstein and the Cubs’ new front office brass were down on LeMahieu's lack of pull power. Eight years later, he’s a three-time All-Star with three Gold Gloves on his mantle. And while he’s benefited from playing at Coors Field and Yankee Stadium, Lemahieu is a career .302 hitter with a .354 on-base percentage.
4. Dennis Eckersley to A’s (1987)
Cubs receive: OF Dave Wilder, INF Brian Guinn, RP Mark Leonette
A’s receive: CL Dennis Eckersley, INF Dan Rohn
Eckersley was an effective starter for the Cubs (3.63 ERA, 3.24 FIP, 1.170 WHIP) from 1984-86 but turned into a Hall of Fame closer in Oakland. The right-hander saved 320 games from 1987-95, posting a 2.74 ERA, 2.44 FIP and 0.953 WHIP.
Eckersley made four All-Star teams, won a Cy Young and MVP award and finished in the top six in voting for both awards three other times. Collectively, Wilder, Guinn and Leonette never appeared in a single big league game.
This trade was bad, but it’s not like the Cubs traded their own future Hall of Famer closer. Oh, wait…
3. Lee Smith to Red Sox (1987)
Cubs receive: SP Al Nipper, RP Calvin Schiraldi
Red Sox receive: CL Lee Smith
Remember when I said Cubs GM Jim Frey desperately wanted a closer? He had one in Smith, but when the closer reportedly asked to be traded, Frey (who managed the Cubs from 1984-86) obliged.
Smith saved 298 games from 1988-97, posting a 3.15 ERA. He made five All-Star teams during that span, finishing top five in the Cy Young voting three times. Meanwhile, the Cubs used seven different closers across the same span, the final 10 seasons of Smith's career.
Nipper and Schiraldi weren’t all that bad but had short tenures in Chicago. Either way, the Cubs didn’t get a good enough return for Smith, who was elected into the Hall of Fame last year — wearing a Cubs cap, funny enough.
2. Bill Madlock to Giants (1977)
Cubs receive: OF Bobby Murcer, 3B Steve Ontiveros and RP Andy Muhlstock
Giants receive: 3B Bill Madlock, INF Rob Sperring
Madlock, who won back-to-back NL batting titles in 1975 and ’76, sought a multi-year contract extension worth $200,000 annually. The Cubs balked, dealing him to San Francisco while handing Murcer a five-year deal worth $320,000 annually (both totals per the New York Times).
Madlock hit .294 with a .355 OBP in 11 seasons post-trade, making two All-Star teams. Murcer was an All-Star each season from 1971-75, but he hit .270 with a .367 OBP in parts of three seasons on the North Side. The Cubs dealt him to the Yankees in June 1979 to shed his contract.
Third base was a revolving door for the Cubs until they acquired Aramis Ramirez in July 2003.
1. Lou Brock to Cardinals (1964)
Cubs receive: SP Ernie Broglio, P Bobby Shantz and OF Doug Clemens
Cardinals receive: OF Lou Brock, RP Jack Spring and P Paul Toth
This trade is widely considered the worst in MLB history, and it even has its own Wikipedia page. (Yikes.)
Brock posted modest numbers from 1961-64 with the Cubs (.257, .306 OBP) and Broglio went 18-8 with a 2.99 ERA (3.70 FIP) and 1.168 WHIP in 1963. It seemed the Cubs were the clear winners of the trade, only Broglio was out of baseball after 1966, his age-30 season.
Brock hit .297 with a .347 OBP in 16 seasons with St. Louis. He stole 888 bases, leading all of baseball six times and the NL another two. He made six All-Star teams, finishing his career with 3,023 hits and 938 swiped bags — then the most in MLB history.
Brock won two World Series with St. Louis, and the Cubs suffered a 38-season postseason drought post-1945. Not only did they trade a future Hall of Famer, but they traded him to their No. 1 rival. Ouch.