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When a team acts as a buyer at the MLB trade deadline, it usually signals a clear push for postseason contention. The Chicago Cubs embraced that role this season, executing one of their most aggressive deadline strategies in recent years. Their primary need was pitching, and they addressed it emphatically.
Initial grades were assigned to each move at the time. Now, with the NL Wild Card Series just days away, it's time to reassess whether these trades have positioned the Cubs for a deep October run or left them with regrets.
Kevin Gausman: Mixed Results in Chicago
The Cubs' first major addition was right-hander Kevin Gausman, a frontline starter acquired from the Toronto Blue Jays. The 35-year-old, set to hit free agency after the season, has not met the lofty expectations placed upon him. Once projected to lead the Cubs in WAR for the remainder of the season, Gausman has posted a 5.04 ERA over eight starts and 44.1 innings. He had a 4.38 ERA in 23 starts with Toronto before the trade.
Gausman's September has been a roller coaster: a seven-inning, one-run gem against Milwaukee, followed by a four-inning, six-earned-run debacle versus the same team, and then a 5.2-inning, two-earned-run outing against Atlanta. His postseason track record is solid, with a 3.83 ERA in 56.1 playoff innings over his 14-year career, including a World Series run with the Blue Jays last season. How he performs in October will be closely watched.
Prospects Sent to Toronto
In exchange for Gausman, the Cubs sent infielder Ty Southisene and outfielder Brett Bateman to Toronto. Southisene is now the Blue Jays' No. 17 prospect and is hitting .262 with an .809 OPS in High-A. Bateman has made his MLB debut and become an everyday outfielder for Toronto, slashing .320/.394/.413 (.807 OPS). He could have been a Rookie of the Year candidate with a full season of playing time. The Cubs likely saw no clear path for a 24-year-old center fielder given their current star at the position.
Instant grade: B+ Re-grade: B
Clay Holmes and Tyrone Taylor: A Tale of Two Impacts
The Cubs made a bold move to acquire right-hander Clay Holmes and outfielder Tyrone Taylor. Holmes, 33, had a limited 2026 sample due to a shin fracture, but in August he was stellar, posting a 1.55 ERA in five starts and 29 innings. However, he has struggled in three September starts, allowing 16 earned runs in 15.1 innings, including a six-earned-run outing against Cincinnati.
Interestingly, Taylor has arguably been the more impactful addition. The Cubs had tried a similar platoon approach last year with Willi Castro, which failed miserably (.170 average, .485 OPS in 34 games). Taylor, however, has thrived, slashing .343/.387/.493 (.879 OPS) in 28 games. He has already accumulated 0.9 bWAR as a Cub, while Holmes has 0.3.
In return, the Mets received infielder Jefferson Rojas, once the Cubs' top prospect. The 21-year-old hit .308 with a 1.037 OPS in Triple-A after the trade and could be in the majors by Opening Day next season. While it's too early to judge Rojas's big-league future, the immediate impact of Holmes and Taylor on a playoff-bound team is what matters now.
Instant grade: A- Re-grade: A
Braxton Garrett: A Perplexing Acquisition
The Cubs' acquisition of left-hander Braxton Garrett from the Miami Marlins raised eyebrows. Garrett had pitched only 4.1 innings in 2026 with a 14.54 ERA, though he had a 2.90 ERA in 77.2 innings at Triple-A for the Marlins. Since joining the Cubs, he has yet to appear in the majors and has struggled at Triple-A Iowa with a 4.11 ERA in 30.2 innings. Under team control through 2028, Garrett's future with the club is uncertain, but for now, this trade has had minimal impact.
Miami received infielder Jonathon Long and right-hander Jace Beck. Long, formerly the Cubs' No. 13 prospect, hit .275 with 16 homers and an .816 OPS in combined Triple-A stints. Beck, signed to a minor league deal last offseason, struggled in Triple-A for both organizations (6.60 ERA with the Cubs, 6.66 with the Marlins).
Instant grade: B- Re-grade: D+
Ryan Zeferjahn: Upside Amid Struggles
Reliever Ryan Zeferjahn, acquired from the Los Angeles Angels, was viewed as a high-upside arm under club control through 2030. However, his 16.1 innings with the Cubs have been disappointing: a 4.96 ERA (up from 3.66 with the Angels) and a 1.53 WHIP (up from 1.20), with two blown saves in 18 appearances. Still, Zeferjahn has been lights-out in his last seven games, posting a 1.42 ERA and two saves. If he carries that into the postseason, Cubs fans will quickly forget his August struggles.
The Angels received catcher/first baseman Moises Ballesteros and right-hander Mason McGwire. Ballesteros, a fan favorite in Chicago, has struggled in Los Angeles, hitting .208 with a .560 OPS. McGwire, son of MLB legend Mark McGwire, was also part of the deal.
Instant grade: C+ Re-grade: B+
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