Oct 13, 2026 9:30 PM
From Alex Bregman’s blockbuster arrival to Michael Conforto’s bench heroics, we grade the high-stakes roster moves that defined the North Siders’ latest pursuit of postseason glory.
The Chicago Cubs didn’t need to address their offense much last offseason.
They already had a core of Carson Kelly, Michael Busch, Nico Hoerner, Dansby Swanson, Ian Happ, Pete Crow-Armstrong, and Seiya Suzuki. The Cubs were likely looking for one high-level starter and a few backup options in free agency.
That’s exactly how last offseason played out, as the Cubs signed Alex Bregman (high-level starter) and a few backup options (Michael Conforto and Tyler Austin). Let’s look at each move and grade it.
Alex Bregman
The Cubs swung big in free agency by signing Bregman to a massive five-year, $175 million deal. The team needed another solid hitter at the top of the lineup and got exactly that with the 11-year veteran.
Bregman slashed .265/.355/.464 with 28 home runs, 33 doubles, two triples, 93 RBI, and three stolen bases in his first season with the Cubs. Although he struggled a bit in the first half, the 32-year-old third baseman figured it out down the stretch and finished with an impressive 5.8 WAR.
This was obviously a nice pickup for the Cubs last offseason. He’s exactly the type of hitter that the North Siders needed, and he stepped up in plenty of key spots throughout the year.
Grade: A
Michael Conforto
The Cubs signed Michael Conforto to a Minor League contract with an invitation to Major League spring training last offseason. Conforto eventually made his way onto the Opening Day roster after a solid spring.
Conforto really played his role well with the Cubs. He was that fourth outfielder who saw a lot of pinch-hit opportunities. The lefty-swinging outfielder thrived in that role, hitting .300 with five home runs and 10 RBI as a bench bat.
Conforto was a nice pickup by the Cubs. He was a reliable bat off the bench and posted solid all-around numbers. The 33-year-old slashed .240/.331/.469 with 15 home runs, 17 doubles, and 45 RBI across 113 games.
Grade: A
Tyler Austin
When the Cubs signed Tyler Austin in the winter, they expected him to back up Busch for the season. Austin spent the last few seasons playing in the Nippon Professional Baseball (NPB) Organization, where he hit .280 with 12 home runs and 31 RBI across 72 games in his last season there.
However, Austin underwent a right knee patellar tendon debridement procedure in spring training that caused him to miss the entire season. He could have been a nice right-handed bat off the bench, but his injury kept him out of 2026.
Grade: N/A
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