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A look at Cubs trades in the expansion era: 2019

Some deals were made to try to put the Cubs back in the postseason.

Photo by Nuccio DiNuzzo/Getty Images

As would happen again in September 2023, the Cubs had a playoff spot in hand in September 2019, only to go on a nine-game losing streak that was one of the worst collapses in franchise history.

Some of these deals might look a bit different in hindsight had the Cubs made the playoffs.

March 9: Acquired Donnie Dewees from the Royals for Stephen Ridings

Or, more accurately, RE-acquired Dewees, as the team had traded him to Kansas City a little more than two years earlier for Alec Mills.

Dewees never played in the major leagues. Ridings never pitched for the Royals, so for the two teams involves this was a nothing deal. Ridings, who was the Cubs’ eighth-round pick in 2016 from Haverford College, eventually pitched in five MLB games for the Yankees in 2021. He was released by the Mets last June.

July 15: Acquired Martin Maldonado from the Royals for Mike Montgomery

This was one strange trade. Montgomery had originally been a No. 1 pick of the Royals (36th overall) in 2008 out of high school in California, but they traded him to the Rays four years later in the deal where they got Wade Davis. Then he went from Tampa Bay to Seattle in 2015 for Erasmo Ramirez, and later to the Cubs.

Montgomery posted a 4.67 ERA and 1.529 WHIP in 16 games (14 starts) for the Royals in 2019 and 2020, for 0.5 bWAR. Eventually he wound up in KBO in Korea, where he went ballistic after being ejected for delaying a game:

He pitched in the Mets system in 2022 and the Dodgers system last year.

As for Maldonado, he had been a very good defensive catcher who could hit, at least for a bit of power (15 doubles and six home runs for the Royals in 74 games) and the reason the Cubs made this deal was that they were hurting for a catcher in July 2019 because Willson Contreras had gotten hurt again and the team was desperate for anyone to back up Victor Caratini while Contreras was out, and they didn’t know how long Contreras would be out at the time.

And then Joe Maddon simply wouldn’t play Maldonado. He started four games and went 0-for-11 with five strikeouts. He seemed very unhappy and the team appeared to be not real happy with him, either. The last game he played in was July 22. Contreras was activated July 24 (with Addison Russell optioned to Iowa as the corresponding move) and Maldonado sat on the bench, not even pinch-hitting, before he was traded away.

July 30: Acquired David Phelps from the Blue Jays for Thomas Hatch

This was a desperation trade. The Cubs needed relief help, and Phelps did pitch well: 3.18 ERA, 0.3 bWAR in 24 games. Then he left as a free agent, and pitched for the Brewers, Phillies and back to the Jays again before hanging ‘em up after 2022.

Hatch had been the Cubs’ third-round pick out of Oklahoma State in 2016. He had middling results as a starter in the Cubs system, but the Jays eventually put him in the bullpen. He threw well for them in the 2020 pandemic season, not so much after that, and in 2023 was with the Pirates.

Hatch posted 0.1 bWAR in Toronto so I guess the Cubs “won” this deal.

July 31: Acquired Nick Castellanos from the Tigers for Alex Lange and Paul Richan

Again, this is a deal that Cubs fans would probably have been okay with, even with Castellanos leaving as a free agent after the season, if they had made the postseason. But they didn’t.

And that was certainly not Castellanos’ fault. He played very, very well for the Cubs, batting .321/.356/.646 with 21 doubles and 16 home runs in just 56 games. Many Cubs fans wanted the team to keep him. They didn’t. He signed a four-year contract with the Reds, wasn’t good the first year, was much better the second, then opted out and signed a five-year deal with the Phillies. Again, he had a rough first season in Philly, though played well in the 2022 postseason, and was better the second.

Should the Cubs have kept Castellanos? It’s a reasonable question.

As for Lange, who had been a first-round pick (30th overall) of the Cubs in 2017, it took two years but he finally made the Tigers as a reliever. In 2023 he became their closer, posting 26 saves in 32 opportunities.

Paul Richan, the Cubs’ second-round pick in 2018, never played in the majors.

July 31: Acquired Tony Kemp from the Astros for Martin Maldonado

Maldonado’s 16-day, four-game stint as a Cub is one of the shortest in franchise history for anyone with as much MLB experience as he has — he played in 448 games with the Astros after the deal, posting 1.9 bWAR and getting a World Series ring with them in 2022. He’ll be playing for the White Sox in 2024. It just made no sense for the Cubs to trade for him for that short period while Contreras was out. They probably should have just recalled Taylor Davis to back up Caratini.

Kemp, who had been a reasonably good infielder in Houston, hit .183/.258/.305 in 44 games with the Cubs and had -0.1 bWAR. During that nine-game losing streak that put the Cubs out of contention, he was rung up looking on this pitch that wasn’t even close to being a strike [VIDEO].

That’s just how it went for the Cubs in that stretch. Kemp played reasonably well for the A’s through 2023 after being traded there following the 2019 season.

July 31: Acquired Brad Wieck from the Padres for Carl Edwards Jr.

Edwards, who pitched very well for the Cubs through 2018, was terrible in 2019 (8.47 ERA in 22 games), and it was thought a change of scenery for both pitchers might help.

He didn’t do much in San Diego, and drifted through stints in Seattle, Atlanta and Toronto before landing in Washington in 2022. He had two good years there (3.07 ERA in 89 games, 1.9 bWAR) and is currently a free agent. The Cubs ought to think about bringing him back. He’s only 32.

Wieck looked pretty good at times for the Cubs, but had multiple injury issues and a heart problem that kept him off the field after 2021. He is, as far as I can tell, still in the Cubs organization, even though he hasn’t been on the field since ‘21.

The Cubs made no player-for-player trades in calendar year 2019 after the Wieck deal.

Most of these deals were meh. The Castellanos trade, viewed just for what he gave to the Cubs, was a good one — but then there’s the letting him go part. The photo at the top of this post shows Castellanos sitting in the dugout after the mind-boggling loss to the Cardinals in the last home game of 2019, perhaps thinking about what might have been. Overall I can’t give the 2019 deals more than a C.


Give the Cubs a grade for their 2019 trades.

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