Reviewing the Cubs' 2025 Trade Deadline Moves

[Jeremy Tecktiel]

Image courtesy of © David Banks-Imagn Images

 

As we near July and get into the full swing of trade season, it's worth going back and looking at the 2025 trade deadline to review how it went for the Cubs. Jed Hoyer and Carter Hawkins were busy, making four trades on deadline day last year in an effort to bolster their championship hopes. Let’s go through them one by one. 

Trade 1: 

• Cubs get: RHP Andrew Kittredge
• Orioles get: INF Wilfri De La Cruz

Kittredge was exactly what the Cubs hoped for when they acquired him. He provided 21 2/3 quality innings over the final two months and appeared in five of the Cubs' eight playoff games, even starting one game as an opener. Contending team trades lottery ticket for non-contending team’s reliever is among the most common trade archetypes, and that is exactly was this was. De La Cruz has been ok in his stateside debut this season at 18 years old, walking more than he has struck out but not doing a whole lot else. This trade will truly take years to evaluate, but I will call this a win for the Cubs, right now. They understood the risks and got what they paid for.

Trade 2:

• Cubs get: RHP Michael Soroka
• Nationals get: SS Ronny Cruz and OF Christian Franklin

A former top prospect who reached the majors at 20 years old but constantly struggled to stay healthy, Soroka was the only starter of the three pitchers the Cubs acquired. He had a solid if unspectacular first half in Washington, but he started 16 games after not having started more than 10 since 2019, his lone All-Star season. He started exactly one game in a Cubs uniform before coming out after two innings and going on the IL until mid-September, when he came back for a few appearances out of the bullpen.

Luckily, the Nationals' return has not been overwhelming since the trade. Ronny Cruz is scuffling in High-A this season with a sky-high strikeout rate. Christian Franklin was in Iowa last season and remains in Triple-A this season for the Nationals. It doesn’t look like he will be making much of an impact in the big leagues, and he would not have a role on this Cubs team. Call this one incomplete, because Soroka has pitched really well in 2026 with Arizona. Had he stayed healthy, he would have been exactly what the Cubs were looking for, but knowing the health risks, the Cubs did not give up too much.

Trade 3:

• Cubs get: UTIL Willi Castro
• Twins get: RHP Ryan Gallagher and RHP Sam Armstrong

The Cubs got in on the Twins' fire sale when they snagged Willi Castro to bolster their bench. It did not go as they had hoped. Castro really struggled on the North Side, with a .170/.245/.240 slash line in 110 plate appearances. He was on the playoff roster, but did not get a plate appearance despite coming in to two games.

Gallagher is a 23-year-old who has spent the bulk of this season in Triple-A for the Twins, with some pretty rough results over his 10 starts. Armstrong, 25, has made 14 starts at Double-A this year, with pretty average results. Castro was not good in a Cubs uniform and, although Gallagher and Armstrong have not been good, the Cubs probably wish they still had two extra depth arms in the upper minor leagues this season. It isn’t a disaster, but it probably isn’t one the Cubs would make again, with hindsight. 

Trade 4:

• Cubs get: LHP Taylor Rogers
• Pirates get: OF Ivan Brethowr

A steady presence out of the bullpen, the Cubs got the lefty Rogers twin from the Pirates. While he was not terrible, he got bit by the home run bug a little bit in his 17 2/3 innings of work in Cubbie blue, giving up four long balls. He pitched only one inning in the playoffs.

Brethowr, a college outfielder who was drafted in 2024 in the 7th round, was in High-A for the Cubs at the time of the trade, with an OPS just north of .700. He has played 22 games in Double-A for the Pirates with a .624 OPS in 2026. The Cubs did not risk a lot in this trade to bring in the veteran, and although he didn’t pitch all that well for the Cubs, it is unlikely to come back to bite them. 

After a year, the Cubs' deadline looks a bit like a wash. None of the four players they acquired remain in the organization, and only Kittredge made any real impact in the playoff run. They did not give up much value, but they also did not get the playoff impact they were hoping for. If the Cubs are looking for players at this year’s deadline who will impact their playoff run, they may have to give up a little more value from what is a fairly weak farm system. 

 

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