A continuing series examining past Cubs trades, and whether they moved the needle to creating a winning team.
The Epstein/Hoyer Contention trades – Year 5
2018 had been about as frustrating as could be for a winning team. A 95-win season was spoiled by an improbable run by the Milwaukee Brewers that tied up the division lead on the final day. Then, back-to-back losses in 1-game playoff games, including a 1-0 defeat at the hands of Kyle Freeland and the Colorado Rockies was the rotting cherry on top of a ruined sundae.
The Cubs had done very little on the trade front, dumping Tommy LaStella and picking up Rowan Wick. While they would sign Craig Kimbrel to a free-agent deal during the season, the big pickup in the offseason was Daniel Descalso – not exactly impressive. Although, they did not lose too many players: Jesse Chavez, Daniel Murphy and Justin Wilson being the key losses. In addition to Descalso, they also added Bad Brach, Kendall Graveman and Xavier Cedeno to bolster the bullpen.
2019 In-Season Trades
Date: July 15, 2019
Cubs trade: Mike Montgomery (0.5)
Royals trade: Martin Maldonado (-0.4)
WAR comparison: Royals 0.5 – Cubs -0.4 (Cubs -0.9)
Intangibles: Maldonado was flipped after 4 games to the Astros for Tony Kemp. None of those players made any playoff appearances for either team.
Analysis: World series hero Mike Montgomery’s time with the Cubs had grown sour in 2019. He wanted to be a starter, but they wanted him to be a reliever. The Cubs had two good catchers in Willson Contreras and Victor Caratini, but Contreras had suffered a minor foot injury, and the Cubs needed a temporary backup. So it made sense that two weeks later, at the trade deadline, Maldonado was moved on to the Astros. Montgomery got his wish to go back to starting – with 13 starts for the Royals. But he only made 1 start and 3 appearances in 2020 before a lat strain cost him the rest of the season. He signed with several other teams – the Dodgers, Yankees and Mets (twice) – but did not get back to the majors. We’ll get to Maldonodo soon.
https://www.espn.com/mlb/story/_/id/27199307/cubs-acquire-catcher-maldonado-royals
But any talk about Mike Montgomery gives an excuse to post this:
https://www.mlb.com/video/montgomery-on-getting-final-out-c1211087083
Date: July 30, 2019
Cubs trade: cash
Giants trade: Derek Holland (-0.3) and cash
WAR comparison: Giants 0.0 – Cubs -0.3 (Cubs -0.3)
Intangibles: None
Analysis: The free agents the Cubs had signed to help the bullpen were terrible. Key signings Craig Kimbrel and Brad Brach had a 6.52 and 6.13 ERA respectably. And holdovers Mike Montgomery and Carl Edwards, Jr. had not fared much better. So they went far and wide to bolster the bullpen. Holland was not good, with a 6.89 in 20 appearances for the Cubs. One
https://www.espn.com/mlb/story/_/id/27263925/cubs-acquire-holland-giants-recall-happ
Date: July 30, 2019
Cubs trade: Thomas Hatch (0.1)
Blue Jays trade: David Phelps (0.3)
WAR comparison: Cubs 1.0 – Nationals 0.1 (Cubs +0.9)
Intangibles: Hatch pitched in 2 games for the Toronto Blue Jays in the 2020 playoffs, logging two perfect innings. The Jays were swept in two games by the Rays.
Analysis: Phelps was not bad for the Cubs, with a 3.63 ERA over 17 innings in 24 appearances. Hatch was a 3rd round pick in 2016, who I barely remembered. He did pitch for the Twins last season – but then again, who didn’t.
https://www.espn.com/mlb/story/_/id/27288022/cubs-acquire-reliever-phelps-blue-jays
Date: July 31, 2019
Cubs trade: Carl Edwards, Jr. (-0.2)
Padres trade: Brad Wieck (0.8)
WAR comparison: Cubs 0.8 – Padres -0.2 (Cubs +1.0)
Intangibles: None
Analysis: I still wish Edwards would have been able to close out the World Series Game 7 victory, instead of Montgomery. But after three good seasons with the Cubs, things went south. He had a 5.87 ERA in 2019 before being traded, and then only appeared in 2 games for the Padres. He had a brief stint with the Mariners in 2020, and split 2021 between Atlanta and Toronto. There was a brief resurgence with the Nationals in 2022 and 2023 (89 games with a 3.07 ERA) but only 5 appearances in the past 2 seasons (including time in the minors for the Cubs in 2024). It’s a bit surprising that a guy with a 3.56 lifetime ERA has not gotten more opportunities, but his control has been an issue, even when he was good.
Wieck was decent enough for the Cubs, but the tall left-hander had injury issues, and was never much of a factor.
https://www.mlbtraderumors.com/2019/07/cubs-trade-carl-edwards-jr-padres.html
Date: July 31, 2019
Cubs trade: Paul Richan (minors) and Alex Lange (1.2)
Tigers trade: Nick Castellanos (1.7) and cash
WAR comparison: Cubs 1.7 – Tigers 1.2 (Cubs +0.5)
Intangibles: Lange was still with the Tigers through 2025, but has not pitched in the playoffs the last two seasons. He was recently released and picked up by the Royals. Castellanos did everything he could to get the Cubs close to the playoffs, but it wasn’t enough.
Analysis: Perhaps one of the best rental trades the Cubs have ever made (as the renter) – but the fact that the Cubs still fell short of the postseason puts a damper on it. Castellanos absolutely raked with the Cubs, slashing .321/.356/1.002 and hitting 16 home runs in only 51 games. Overall, he’s had a fairly mediocre career, averaging just over 1.0 WAR over 13 years. But he’s timed his best seasons very well. After blowing up with the Cubs, he got a 2-year $30 million from the Reds. He only produced a .784 OPS in the shortened 2020 season, but then came back in a big way in 2021, with 34 homers, 100 RBI and a .939 OPS. This convinced the Phillies to give him a 5-year, $100 million deal. He managed only a 1.2 WAR over the first 4 seasons, including a -0.8 in 2025. Many wanted the Cubs to re-sign him after his heroics in 2019, but is probably best that they did not. He was never a great defender, but he’s only gotten worse, and his offense has not made up for it.
https://www.espn.com/mlb/story?id=27298027&src=desktop
Here are some of the highlights – including getting to hear Thom Brennaman mispronounce his name a couple of times.
Date: July 31, 2019
Cubs trade: Martin Maldonado (2.0)
Astros trade: Tony Kemp (-0.1)
WAR comparison: Astros 2.0 – Cubs -0.1 (Cubs -2.1)
Intangibles: Maldonado was a free-agent but re-signed with the Astros. Despite his limited offensive production, he was counted on in the postseason for 6-straight years, racking up 202 plate appearances. His postseason slash line of .169/.253/.249 is amazingly low, but his defense framing and pitcher-handling must have been enough.
Kemp was traded in the off-season to the Athletics.
Analysis: Maldonado was not really necessary, as Contreras came back from injury. Kemp did not do very much for the Cubs, only appearing in 4 games.
https://www.espn.com/mlb/story/_/id/27295620/cubs-trade-catcher-maldonado-astros-kemp
Pre-2020 Season Trades
Date: January 13, 2020
Cubs trade: Tony Kemp (3.5)
Athletics trade: Alfonso Rivas III (0.4)
WAR comparison: Athletics 3.5 – Cubs 0.4 (Cubs -3.1)
Intangibles: None
Analysis: Kemp was a good utility player for the A’s for a few years, including playing in 147 games in 2022. His production fell of drastically in 2023, and he played sparingly in 2024.
Rivas seems like a decent prospect, but while he was good at getting on base, (.388 OBP in 2021) he did not slug. He was released in 2023, playing for the Padres and Pirates that season.
https://www.espn.com/mlb/story?id=28477663&src=desktop
WAR Scorecard for 2019 in-season and post season
Gained WAR: 2.4
Lost WAR: 9.2
NET: -6.8
Updated Scorecard for Epstein/Hoyer:
Gained WAR: 124.4
Lost WAR: 80.1
NET: +44.3
The Cubs somehow had a negative WAR for all three of the trades that sent Montgomery for Maldonado, Maldonado for Kemp, and Kemp for Rivas. And while the Castellanos trade was very good, it was also short lived. The Cubs finished third in the Central at 84-76, 7 back of the NL Central champion Cardinals and 5 games behind the Brewers, who were the second wild card team. They Rivas trade was the only one that made in the offseason before 2020.
Cubs in 7 
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