The Five Most Important Cubs' Midseason Trades Since 2000

[Paul Niemiec]

Image courtesy of © Ken Blaze-Imagn Images

The trade deadline is a week away, and we are looking at the most promising Cubs team since… 2020?... 2019?... 2018? There were hints of competitiveness in 2023, and a slight increase was observed in 2024. Now, they look like a team that can make a deep playoff run, but the roster isn’t complete yet. They need help if they want to reclaim the division from a rejuvenated Milwaukee team. It has been years since the Cubs looked like genuine buyers, so it should be an exciting time for fans. In the spirit of trade season, let's look back on some of the most meaningful mid-season moves the Cubs have made over the last 25 years. This only covers mid-season trades, so that you won't find discussions about moves like Derrek Lee or Kyle Tucker in here. 

July 2nd, 2013: Cubs Trade for Jake Arrieta & Pedro Strop from Baltimore
This wasn’t a deadline deal, but this is one of the first trades that helped pry open the championship window. Once upon a time, Baltimore had a three-headed monster of young pitching prospects in the pipeline: Brian Matusz, Chris Tillman, and Jake Arrieta. Well, the three-headed monster was just in theory. This is because, even as late as the late 2000s, Baltimore still struggled to develop pitching. Arrieta had a 5.46 ERA across 348 innings from 2010 to 2023, and his prospect stock was fading fast. Baltimore could not afford to keep him around when they were eying a playoff spot in 2013. Scott Feldman, who went back to Baltimore along with Steve Clevenger, had a 3.46 ERA across 91 innings at the time of the trade. At the time, this was seen as Baltimore trading for a dependable, yet unspectacular, veteran starter and only giving up a young pitcher in desperate need of a change of scenery. A season and a half later, Arrieta won the N.L. Cy Young, and we all know what he helped accomplish the following season. Arrieta is the star of the deal, but Pedro Strop became one of the most reliable Cubs relievers we have seen since 2000. He owns a 2.88 ERA across eight seasons with the team, and posted the lowest WHIP of his career (.887) in 2016. 

---

July 23rd, 2003: Cubs Trade for Aramis Ramirez from Pittsburgh
There is a strong argument that this is the best trade that Jim Hendry made as General Manager of the Cubs. At the time of the trade, Ramirez was a 25-year-old third baseman who posted negative WAR in four out of five seasons, but had one season with 4.1 WAR, a .300 batting average, and 34 homers. The Cubs were fighting for first place in the division but had a glaring hole at third base (sound familiar?), and the Pirates were well under .500. Pittsburgh also had aging speedster Kenny Lofton on their roster, who was completely disposable. Corey Patterson went down with an injury, and the tandem of Ramon Hernandez and Mark Bellhorn was not holding down the hot corner. This trade filled center field for a competitive 2003 season (all I will say about 2003) and also happened to give them an .887 OPS, 234 home runs, and a .294 batting average at third base for the next nine seasons. Of the three players the Cubs gave up, only infielder Bobby Hill reached the majors, where he put up 0.3 WAR from 2002-2005. 

---

July 17th, 2017: Cubs Trade for Jose Quintana from White Sox
Did you think I was only going to cover winning trades? No, the title says most memorable, which could be positive or negative. The Cubs were coming off a bit of a World Series hangover in 2017, and while they were still division champs, that magical feel from 2016 was fading. Reclamation project Eddie Butler, nor Mike Montgomery, were doing an adequate job at holding down the 5th starter spot following the departure of Jason Hammel. The Cubs' rotation as a whole seemed to be a shell of its former self in 2017, so a mid-to-front-line rotation arm was needed. Enter Jose Quintana, a 2016 All-Star, and owner of a 3.51 ERA over his previous six seasons with the White Sox. Quintana was also under team control for four more seasons, so this was as much of a “win later” move as it was a win-now move. Plain and simple, Quintana never quite figured it out for the Cubs. He was not bad, as evident by his 4.24 ERA over 78 starts, but he was not the same guy he was on the South Side. In hindsight, this deal worked out to be not as ugly as originally thought. Former number one Cubs prospect Eloy Jimenez was about as big of a bust as anyone in recent memory, most recently being released by the Rays without playing a major league game for them. The Cubs had ideas of using #4 prospect Dylan Cease as a reliever, so maybe he would not have had the same career trajectory if he stayed on the North Side. You have to think this could come full circle for the Cubs, with Cease set to be a free agent after this season, but that is a whole different article.

---

July 30th, 2021: Cubs Trade Javier Baez, Trevor Williams to Mets for Pete Crow-Armstrong
Nick Madrigal, Codi Heuer, Alexander Canario, Caleb Kilian Alexander Vizcaino, and Pete Crow-Armstrong were the haul acquired over that 24-hour period, where we saw Anthony Rizzo, Kris Bryant, Baez, and Craig Kimbrel traded, signaling the end of an era. Before 2025, would we have considered these moves a success four years later? Probably not, but that was then, and this is now. Madrigal, Heuer, Canario, Killian, and Vizcaino have produced a combined 4.2 WAR for their careers up to this point (with Vizcaino not appearing in the majors). Crow-Armstrong is at 8.1 career WAR, with 5.9 of that coming in 2025. I think every Cubs fan would happily accept nothing from the five players acquired besides Crow-Armstrong if they knew that he would become a star. Currently challenging Ohtani for the MVP race, Crow-Armstrong has exceeded scouts’ expectations by becoming one of the best bats in baseball. A former first-round high school pick, he was projected to be a plus defender who could become a major league regular if he could hit consistently. The Cubs initially wanted pitcher Matt Allan from the Mets, but they refused to include him in the package. Allan’s career has since been put on hold due to a hodgepodge of injuries. Crow-Armstrong's emergence, combined with many other bright spots on the 2025 team, is why the Cubs are returning to serious contender status in the National League. It is heartwarming to see a direct lineage between this group and the championship core. 

---

July 25th, 2016: Cubs trade for Aroldis Chapman from Yankees
Last but certainly not least, we have what should be considered the greatest trade in Cubs history, whether it was a rental or not. The Cubs were 59-38, leading the division by 7.5 games, when they made the trade. Chapman was a candidate to be traded all season by the retooling Yankees and was widely viewed as the final piece to put the Cubs over the top in a season where Vegas had their odds at winning the World Series at 4 to 1. They rode Chapman hard in the playoffs; he pitched 15 ⅔ innings, which was more than starting pitcher John Lackey. With all due respect to the other relievers like Hector Rondon, Pedro Strop, Travis Wood, and Mike Montgomery, this team likely does not win without Chapman. Game four of the NLDS, where Chapman struck out the side to end it, might have looked a lot different with Strop on the mound. The same can be said about game five of the World Series, where he had an eight-out save, striking out four. Chapman did not come cheap, as Gleyber Torres was the Cubs’ top prospect at the time and knocking on the door of the big leagues. With hindsight being 20/20, this trade was a pure win for the Cubs. Gleyber had his 38-homer 2019 season and two All-Star appearances with New York, but outside of that, he has been an above-average but far from a star player.

Other Notable Trades:

July 8th, 2008: Cubs trade for Rich Harden from Athletics
The Cubs needed another starter for their playoff-bound team in 2006. In the trade for Harden, they parted with future MVP Josh Donaldson.

July 31st, 2019: Cubs trade for Nick Castellanos from Tigers
Although the Cubs missed the playoffs due to their late-season collapse, Castellanos hit .321/.356/.646 with a 1.002 OPS over 51 games. 

July 31st, 2023: Cubs trade for Jeimer Candelario from Nationals
Although the Candy Man was not very good for the Cubs, this marked a return to being deadline buyers after the championship core was traded. They fell short of the playoffs, but it was nice to see a competitive season.

View full article