July is fast approaching and with it inevitably comes the flying of trade rumors. The Chicago Cubs still aren't solidified in where they'll land this year - at three games below .500 and behind two NL Central competitors, they're not in the best position for a run. At only three games behind the Brewers and Reds who are tied at the top, however, it would be easy for Jed Hoyer and company to make an excuse to do some light buying this year.
Trade deadlines have been a touchy subject for Cubs fans over the past two years. 2021 and 2022 saw major sell-offs that sent franchise faces and valuable pieces to greener pastures as the team built for the future. Whether as buyers or sellers, however, the Cubs have a long history of shaking it up with midseason deals. Some of these have vastly improved the team's fortunes and brought franchise favorites to town, while others are still sources of derision today.
As we head toward an uncertain 2023 trade season, let's take a look back at three of the best, and two of the worst, deal the Cubs have made at and around the trade deadline.
#1 Best: Cubs acquire Jake Arrieta and Pedro Strop from Baltimore for Scott Feldman
It's hard to find a better trade season deal than landing both a rotation and relief ace in a total steal. That's what the Cubs accomplished in 2013 when they picked up both Jake Arrieta and Pedro Strop for the low low price of Scott Feldman in an early July swap with Baltimore.
From the Orioles' side of things, it's a disaster deal in hindsight. After posting a 3.46 ERA in Chicago, his ERA rose to a mediocre 4.27 in Baltimore. He would also only stick around for the second half of that season before walking and signing with the Astros. The Cubs, meanwhile, would get years of valuable service out of Arrieta and Strop. Arrieta would become the team's ace, winning a Cy Young in 2015 and posting a 2.67 ERA in his four full seasons with the team. Strop, meanwhile, would become a bullpen stalwart with a 2.90 ERA in his six full seasons after 2013.
Of course, both pitchers would be key pieces to the 2016 World Series roster, helping the Cubs form a deadly pitching staff that would be the envy of the league. Both were solid in their appearances against Cleveland, playing their part in breaking the 108-year championship drought.