Five biggest trade deadline deals by the Cubs, Sox
After taking a two-week break from High Five normalcy because of the Olympics, we’ve got some catching up to do.
While the Cubs and White Sox were somewhat quiet at the MLB trade deadline in July, that hasn’t always been the case.
This week’s High Five looks at five blockbuster deals made by the teams since the trade deadline went into effect in the mid 1980s.
We’re bright-siding again, so you won’t see the Cubs’ Lou Brock-for-Ernie Broglio deal from 1964 or the White Sox’s infamous “White Flag” purge that saw the 1997 team dismantled despite being only three-and-a-half games out of first place.
5. 2017
The biggest trade in cross-town history came as the Cubs were trying to win a second straight World Series title.
On July 13, the Cubs acquired starting pitcher Jose Quintana from the Sox and sent four players to the South Side including top prospects Dylan Cease and Eloy Jimenez.
The Cubs got a solid middle-of-the-rotation lefty on a club-friendly deal in exchange for players who were too young to make an impact during the championship window.
The White Sox acquired what was thought to be two future cornerstone players. Cease became the ace of the staff, finishing second in the Cy Young Award voting in 2022. Jimenez was a more highly-touted prospect, but injuries never allowed him to match his first season with the Sox when he slugged 31 homers in 2019.
4. 1984
Technically, this shouldn’t count because it came a couple years before the trade deadline went into effect. But it’s too big to ignore.
On June 13, the Cubs swung for the fences by trading four players, including future two-time World Series champion Joe Carter, to Cleveland for starting pitcher Rick Sutcliffe.
Sutcliffe had been scuffling a bit with Cleveland, but became dominant with the Cubs. He went 16-1 with a 2.69 ERA and won the Cy Young Award. The Cubs claimed the National League East Division title for the first time before falling to the Padres in a heartbreaking NL Championship Series.
3. 2004
The White Sox struck a month early to grab one of the biggest prizes of the deadline — starting pitcher Freddy Garcia.
It wasn’t enough to overtake the Twins for the American League Central title, but the White Sox were building to something much bigger. Garcia went 14-8 in 2005, pitched a complete-game victory in the ALCS and threw seven shutout innings in the World Series clincher against Houston.
Garcia won 17 games for the Sox in 2006 before being traded to the Phillies in the offseason.
2. 2004
The White Sox weren’t done after the Garcia trade. In a true deadline deal on July 31, they acquired starting pitcher Jose Contreras from the Yankees for Esteban Loaiza, who had finished second the year before in the Cy Young voting.
Contreras, who went 15-7 in 2005, started the opener of all three playoff series and pitched at least seven innings in each including a complete game in the clinching win over the Angels in the ALCS.
1. 2013
The Cubs were sellers at the deadline and went on to lose nearly 100 games, but a July deal forever changed the franchise.
Baltimore, trying to contend in the brutal AL East, got starting pitcher Scott Feldman and catcher Steve Clevinger from the Cubs for struggling starter Jake Arrieta and reliever Pedro Strop.
Three years later, Arrieta and Strop were critical in helping the Cubs win the World Series for the first time since 1908.
Arrieta, who earned the Cy Young Award in 2015, went 18-8 in 2016 and won two World Series games. Strop was one of the league’s top setup relievers, posting a 2.84 ERA in 54 appearances.