A continuing series examining past Cubs trades, and whether they moved the needle to creating a winning team.
The *Epstein/Hoyer Contention trades – Year 6
*Epstein resigned in November of 2020
After the best run for the Cubs in 100 years, including 4 straight playoff seasons, 3 NLCS appearances and a World Championship, 2019 had been a splash of cold water. Not even a heroic performance by Nick Castellanos could get the Cubs back to the playoffs, and we had to watch the Cardinals take the NL Central title and the Brewers secure a Wild Card. The only silver linings was seeing the Nationals beat both of them in the playoffs.
But things could certainly get worse, as the World was hit with a global pandemic, and the postponed baseball season was the least of all of our worries. The Cubs had made only one off-season trade before the season, shipping off Tony Kemp to acquire Alfonso Rivas. But with the late start to the season, not trades were amde until the end of August, which was the new trade deadline.
2020 In-Season Trades
Date: August 30, 2020
Cubs trade: Jose Martinez (-0.6)
Rays trade: Pedro Martinez (minors)
WAR comparison: Rays 0.0 – Cubs -0.6 (Cubs -0.6)
Intangibles: None
Analysis: The 2020 Cubs really needed someone who could hit left-handed pitching to pinch hit and DH, and found a cheap option with Jose Martinez from the Rays. As disasters go, this was fairly high up there. The only positive was that Martinez did not get too many at bats, and the player he was traded for never reached the majors. Martinez went 0 for 21 with a walk and seven strikeouts, which added up to a .045 OPS. Needless to say, he was left off of the postseason roster.
https://www.espn.com/mlb/story/_/id/29772907/sources-cubs-acquire-dh-jose-martinez-rays
Date: August 31, 2020
Cubs trade: Ronny Simon (0.0)
Diamondbacks trade: Andrew Chafin (1.5) and cash
WAR comparison: Cubs 1.5 – Diamondbacks 0.0 (Cubs +1.5)
Intangibles: Chafin was then flipped to the A’s for two players, including a very young reliever named Daniel Palencia. Simon was flipped for OF/1B Jordan Luplow, who had a 0.0 WAR in 234 PAs for the DBacks in 2022, and left as a free agent.
Analysis: Chafin was a very nice addition, and while he only pitched in 4 games in the regular season, and for 1 out in the postseason, he followed it up with a very solid 2021. He managed a 1.5 WAR and 2.06 ERA in 43 games in 2021. Simon finally made it to the majors in 2025, but managed a .574 OPS for the Marlins (who waived him) and the Pirates.
https://www.espn.com/mlb/story/_/id/29780646/trying-address-things-done-particularly-well-cubs-gm-jed-hoyer-adds-lefty-relievers-righty-hitters-deadline
Date: August 31, 2020
Cubs trade: Zach Bryant (minors)
Red Sox trade: Joel Osich (-0.5)
WAR comparison: Red Sox 0.0 – Cubs -0.5 (Cubs -0.5)
Intangibles: None
Analysis: Osich was awful for the Cubs, as he allowed 6 runs (3 earned) in only 2.2 innings over 4 games. It’s actually impressive he managed a -0.5 WAR in such a short amount of time. His FIP was 1.32 compared to an ERA of 10.13, perhaps the largest variance between those 2 numbers I’ve ever seen – but it was an EXTREMELY small sample size. The cost was minimal, as Bryant has not gotten past AA, although he is was still in the Red Sox farm system as of 2025.
Date: August 31, 2020
Cubs trade: Zach Short (-0.3)
Tigers trade: Cameron Maybin (0.1)
WAR comparison: Cubs 0.1 – Tigers -0.3 (Cubs +0.4)
Intangibles: Maybin went 0-2 with a strikeout as a pinch hitter in the 2020 playoffs. He was re-signed by the Cubs in the offseason, but was sold to the Mets before 2021 started, and he retired after 9 games there. Short was waived by the Tigers in 2023 and picked up by the Mets.
Analysis: Maybin was more effective as a right handed pinch hitter/outfielder for the Cubs, platooning with Jason Heyward in right field against left-handed pitchers. His .669 OPS wasn’t too impressive, but was an upgrade from what the Cubs had been getting. Short played in 177 games for the Tigers over 3 seasons, but managed a paltry .174/.266/.308 slash line.
Pre-2021 Season Trades
Date: December 29, 2020
Cubs trade: Yu Darvish (8.8) and Victor Caratini (0.0)
Padres trade: Owen Caissie (-0.1), Ismael Mena (minors), Yeison Santana (minors), Reginald Preciado (minors) and Zach Davies (-1.0)
WAR comparison: Padres 8.8 – Cubs -1.1 (Cubs -9.9)
Intangibles: Darvish was given a new contract from the Padres in 2024, but most of his WAR was earned while on the contract from the Cubs. He has pitched in 3 post-seasons for the Padres, and was especially good in the 2022 postseason, going 2-1. Caratini was traded for Korry Howell and Brett Sullivan. Howell only reachec AA, and is nor in an Independent League. Sullivan played in 40 games over two seasons, with poor results (./206/,243/.299), and is now in the Rockies farm system.
On the Cubs side, Caissie has been flipped with Edgardo De Leon and Cristian Hernandez for Edward Cabrera.
Analysis: This trade – along with the inexplicable non-tender of Kyle Schwarber – marked the end of the Cubs contention era of 2015-2021. A last gasp, first-place run in the first half of 2021 turned out to be a mirage, and the Hoyer rebuild began in earnest in July of that season. The Cubs seemed desperate to cut costs and get out from under the remainder of Darvish’s contract, which the Padres were more than happy to take on. The ironic thing is that Darvish performed very well in those last two seasons of the Cubs deal (with the Cubs paying $3 million of the contract). He had 6.0 WAR in ’21 and ’22 combined, but only 2.8 WAR in the 3 injury-impacted seasons since (under a new 6-year, $108-million deal). And now it appears his career may be over. So, it Cubs may have been just a bit premature in predicting when age would derail his career.
For the Cubs, the trade results have been underwhelming. Davies – who was acquired to fill the Darvish’s spot in the rotation – was not good as a single-season stop-gap. And of the prospects they received, only Caissie has reached the majors. And he was recently traded away as part of a package for Edward Cabrera. That leaves 22-year-old Reginal Preciado, who was the #11 Cubs prospect in 2021 and 2022. But he’s only gotten as far as high-A in the Cubs system, and he is no longer in their current top 20 prospects according to Keith Law ($), and was not in the top 30 in 2025 according to MLB.com. With Willson Contreras under contract for 2 more seasons, Caratini must have been seen as expendable, but I wonder if the Cubs could have gotten a better return for him individually.
I’ve mentioned before that rentals typically give a big advantage to the team getting prospects. But this was more of a salary dump, which typically favors the team getting the player getting dumped – and that was definitely the case here.
The other huge off-season move was the resignation of Theo Epstein. He had accomplished his goal of bringing a World Series to Chicago, and with a potential rebuild on the horizon, it was a good time to pass over the reigns to Jed Hoyer. Sometime I wonder whether the Cubs would have had such stringent payroll restrictions if Epstein had stayed, as I think he would have had more leverage with ownership as opposed to the newly promoted Hoyer.
WAR Scorecard for 2020 in-season and post season
Gained WAR: 1.8
Lost WAR: -9.9
NET: -8.1
Final Scorecard for Epstein/Hoyer:
Gained WAR: 126.2
Lost WAR: 90.0
NET: +36.2
Winning a division title in a Covid-shortened season (in empty stadiums), but then getting swept by the Marlins in a best of 3 series was not the worst way for Theo Epstein to go out. But it wasn’t great.. I think almost all Cubs fans felt a great deal of appreciation for what Theo Epstein had accomplished, but there was definitely a feeling that either the party was over or was about to come to an end. The fact that Kyle Hendricks was the only player from 2016 who had a contract extension, and the Schwarber non-tender were both signs that a huge roster turnover was imminent.
But ultimately, the ability to get positive value from trades the Epstein and Hoyer made between 2012 and 2020 was one of the big reasons the Cubs were so successful in that era. Combined with the development of several home grown players (Baez, Bryant, Contreras, Happ, among others) and the signing of some key free agents (including Lester and Zobrist) made this version of the Cubs the most successful in my lifetime.
Cubs in 7 
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