A continuing series examining past Cubs trades, and whether they moved the needle to creating a winning team.
The Epstein/Hoyer Contention trades – Year 3
The Cubs acquired Alec Mills and Wade Davis in the offseason, but did very little in free agency, adding Jon Jay, Zac Rosscup, Koji Uehara, Brett Anderson and Brian Duensing. At the time of the All-Star break, they were under .500 and 5.5 games behind the Brewers in the NL Central, and their opportunity to defend their World Championship seemed precarious. They would ultimately make a trade that would define the next few seasons.
Here are some of the previous entries in this series:
- Introduction
- Epstein/Hoyer rebuild year 1 (2012)
- Epstein/Hoyer rebuild year 2 (2013)
- Epstein/Hoyer rebuild year 3 (2014)
- Epstein/Hoyer Contention year 1 (2015)
- Epstein/Hoyer Contention year 2 (2016)
2017 In-Season Trades
Date: May 8, 2017
Cubs trade: Matt Szczur (0.0)
Padres trade: Justin Hancock (0.3)
WAR comparison: Cubs 0.3 – Padres 0.0 (Cubs +0.3)
Intangibles: None
Analysis: The Cubs needed to DFA Szczur to make room for a bullpen arm. Hancock did not pitch until 2018, and even then pitched sparingly in his only season on an MLB roster.
https://www.espn.com/espn/wire?section=mlb&id=19339968
Date: June 26, 2017
Cubs trade: Zac Rosscup (0.0)
Rockies trade: Matt Carasiti (0.0)
WAR comparison: Cubs 0.0 – Rockies 0.0 (Cubs +0.0)
Intangibles: None
Analysis: Rosscup made 33 appearances for the Cubs in 2015, but none in 2016 and 1 in 2017. He only pitched in 9 games for the Rockies in 2017, and then bounced around with the Dodgers, Mariners, Blue Jays, back to the Dodgers, and finally back with the Rockies for 4 games in 2021. Carasiti never pitched for the Cubs in the majors, pitching in Japan in 2018, briefly for the Mariners in 2019 and the back to the Rockies in 2023 and 2024.
https://www.espn.com/mlb/story/_/id/19745320/rockies-acquire-lefty-rosscup-cubs-righty-carasiti
Date: July 3, 2017
Cubs trade: Miguel Montero
Blue Jays trade: PTBNL or cash
WAR comparison: Cubs 0.0 – Blue Jays -0.6 (Cubs +0.6)
Intangibles: None
Analysis: Montero was brought on in 2015 to be the Cubs regular catcher. He had made the All-Star team twice with the Diamondbacks, but he had to split time with David Ross, who was Jon Lester’s personal catcher. Willson Conteras’ emergence in 2016 cut into his playing time even more, and he was critical of the team even after winning a World Series: https://www.espn.com/mlb/story/_/id/17973532/chicago-cubs-catcher-miguel-montero-critical-manager-joe-maddon-role-team-postseason
Ross had retired, but Contreras took on the job as primary catcher. Things hit a tipping point after Montero was critical of Jake Arrieta after a start, and he was designatedto assignment and then traded: https://www.espn.com/mlb/story/_/id/19758582/cubs-designate-catcher-miguel-montero-assignment-anthony-rizzo-blasts-montero-jake-arrieta-comments
https://www.espn.com/mlb/story/_/id/19797257/toronto-blue-jays-acquire-catcher-miguel-montero-chicago-cubs
Despite the acrimonious end to his tenure, Montero will probably be remembered for two big postseason moments in 2016:
Date: July 13, 2017
Cubs trade: Bryant Fleet (minors), Matt Rose (minors), Dylan Cease (11.5), Eloy Jimenez (5.6)
White Sox trade: Jose Quintana (3.6)
WAR comparison: White Sox 17.1 – Cubs 3.6 (Cubs -13.5)
Intangibles: As mentioned above, at the All-Star Break the Cubs were at 43-45, 5.5 games out of first in the NL Central, and looked in danger of missing the playoffs. The acquisition of Quintana stabilized the roatation and gave the signal that the front office was willing to make the big move to try to defend the title. The Cubs ended up winning the division, and Quintana had a good start in the NLDS. Unfortunately, he was awful in the NLCS against the Dodgers, and that was the last time he pitched in the playoffs for the Cubs. One of the biggest reasons the Cubs acquired him was that he had three additional years of control at a reasonable price, but his ERA was over 4 in each of those 3 years, when it had been under 4 in 5 of 6 seasons for the White Sox. The end of his tenure saw him pitching in only 4 games in 2020 due to cutting his hand in a dishwashing accident: https://www.espn.com/mlb/story/_/id/29399821/cubs-jose-quintana-hurt-washing-dishes-surgery
Meanwhile, Cease and Jimenez were supposed to be the catalysts for the great White Sox revival of the 2020s. Cease, to be fair, was very good for several seasons. Jimenez had his moments, but injuries have completely derailed his career. And the White Sox made the playoff for 2 seasons, in 2020 and 2021 before slipping back to .500 in 2022, and then over 100 losses in each of the past 3 seasons. Cease was amazing in 2022, and finished 2nd in the Cy Young voting, but came back to earth and was traded for 3 pitching prospects and an outfield prospect. Drew Thorpe was the key to the deal, having been acquired by the Padres from the Yankees in the Juan Soto deal. He was identified as a top-100 prospect, and was MLB Pipeline prospect of the year in 2023. Unfortunately, he needed Tommy John Surgery in 2025, so his log-term outlook is a bit fuzzy. Two other prospects in the deal are #17 and #27 in the White Sox top 30. If Thorpe, or one of the other prospects hit, the Quintana deal will look even better for them, and it already looks good. https://www.espn.com/mlb/story/_/id/39726085/padres-finalizing-trade-white-sox-rhp-dylan-cease-sources-say
Jimenez was traded to the Orioles for Trey McGough, and was later released.
Analysis: When the All-Star break hit in 2017, things were not looking good for the Cubs. The euphoria of a World Series title was fading, and a team that Cubs fans hoped would be competitive for years was looking like they might miss out on the playoffs. Something needed to happen. But the front office was not looking for a rental or band-aid. They wanted a starting pitcher with multiple years of control, and that was going to be very costly. In today’s terms, it would have been like giving up Horton and Shaw for MacKensie Gore (which sounds like it was the asking price).
But the results after the trade were great. The Cubs went on a 6-game winning streak including a win for Quintana in a shutout to drop the division deficit to 1.5 games. Another Quintana win in his second start brought the Cubs into a tie. And by July 30th, they had a 2.5 game lead. They went 49-25 in the second half of the season, winning the NL Central by 6 games. It’s the kind of thing you’d expect the Brewers to do, but they went 36-35 to close out the season, and missed the playoffs completely. And they’ve only missed the playoffs once since.
Without that great run, we would not have experienced one of the greatest and craziest games in Cubs history – the NLDS Game 5 win over Washington. And I think the commitment the front office showed by making the Quintana trade really helped the turnaround. Unfortunately, it might have been better to get a rental, as Quintana just did not live up to his previous performances during the last three years of his Cubs career.
Meanwhile, the loss of Cease, on of the few Cubs drafted pitcher who have seen great success in the Major Leagues over the past several years, really stings. There are many things that went wrong that led to the 2021 fire sale and brief rebuild, but not having a home grown top-line pitcher, like Cease, was certainly one of them. There are rumors that the Cubs might was to bring Cease back as a free agent, but I’d say that is unlikely at the moment.
Here are videos of the 2017 NLDS Game 5, just to get some of the bad taste of this trade out of our mouths:
Date: July 13, 2017
Tigers trade: Justin Wilson (0.4) and Alex Avila (0.7)
Cubs trade: Jeimer Candelario (7.8) and Isaac Parades (-0.5)
WAR comparison: Tigers (7.3) – Cubs (1.1) (Cubs -6.2)
Intangibles: Wilson pitched in two postseason games for the Cubs, giving up nothing in 1 total inning. Avila got a single in his only postseason at bat for the Cubs. Candelario has never been to the postseason with any team and Parades did not play in the postseason for the Tigers. The Cubs lost Wilson and Avila, and the Tigers lost Candelario to free agency, but the Tigers were able to trade Parades to the Rays for Austin Meadows. That trade did not work out for the Tigers, as Meadows has not played since 2023 due to mental health issues, while Parades did well with the Rays before being traded to the Cubs and then the Astros (trades we will address later).
Analysis: Wilson was not very good for the Cubs in 2017, with an 88 ERA+. But he was better – though not dominant – in 2018, with a 3.46 ERA. I think there was hope that he could take a higher leverage role in 2018 with Wade Davis leaving as a free agent, as he had been the closer for the Tigers. But Brandon Morrow and Pedro Strop took on the closer duties instead. Avila provided the Cubs with a backup catcher to replace Miguel Montero in 2017, and was solid, but nothing more. Candelario and Parades appeared to be redundant in the Cubs system, as Kris Bryant and Anthony Rizzo had first base and third base, respectively, locked down for the foreseeable future. Of course, that changed in 2021, and the Cubs brought both of the players back for brief stints. Ultimately, I think it was too much to give up for a relief pitcher and backup catcher, as Candelario provided several good seasons at 3rd for a struggling Tigers team. But the Cubs were desperate to fill holes in 2017 in order to compete, which is often why in the long-term, trades typically benefit the team selling at the deadline.
https://www.espn.com/mlb/story/_/id/20205067/chicago-cubs-land-detroit-tigers-closer-justin-wilson-catcher-alex-avila-trade
Pre-2018 Season Trades
Date: October 9, 2017
Cubs trade: Felix Pena (2.3)
Angels trade: Cash
WAR comparison: Angels 2.3 – Cubs 0.0 (Cubs -2.3)
Intangibles: None
Analysis: The Cubs wanted to clear roster space, so they DFA’d Pena and then traded him to the Angels for Cash. He had mild success with the Cubs, and then the Angels.
https://www.espn.com/mlb/story/_/id/20973439/los-angeles-angels-acquire-felix-pena-chicago-cubs
WAR Scorecard for 2017 in-season and post season
Gained WAR: 0.9
Lost WAR 22.0
NET: -21.1
Updated Scorecard for Epstein/Hoyer:
Gained WAR: 112.8
Lost WAR: 68.6
NET: +44.2
Another big hit to NET WAR gained through trades in 2017, as the Cubs were sacrificing good prospects to compete. If Quintana had continued on the trajectory from his White Sox days (12.6 WAR in the 3 years before coming to the Cubs vs 2.3 in the 3 full seasons after he was a Cub), the deficit wouldn’t look nearly as bad.
Shockingly, the Cubs mad only one minor trade between the deadline in 2017 and mid-season in 2018.
Cubs in 7 
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