BREAKING NEWS: Chicago Cubs sign A Good Starting Four in the Rotation to increase their chances returning to the postseason in 2025

The Chicago Cubs could be aiming to acquire another top-tier pitcher for their rotation this offseason. With solid depth and a strong farm system, the team has multiple avenues to enhance the roster and boost their chances of making a postseason run in 2025.

Cubs prospect Kevin Alcantara looking to heat up in Arizona Fall League -  Chicago Sun-Times

Cubs May Be Looking to Add “Ace” in Offseason

A Good Starting Four in the Rotation

The Cubs’ rotation this year included four main starters, led by Shota Imanaga, who posted an impressive 15-3 record with a 2.91 ERA, 1.021 WHIP, and 174 strikeouts over 173 1/3 innings. Imanaga, along with Justin Steele, Jameson Taillon, and Javier Assad, combined for 39 wins and 22 losses across 100 starts.

The remaining starts were handled by Kyle Hendricks (24 starts) and a group of young pitchers like Jordan Wicks, Hayden Wesneski, and Ben Brown. However, that group struggled in 2024, going 10-21 due to injuries and inconsistent performance.

Arrivals and Departures

Kyle Hendricks’ time with the team appears to be nearing its end, while Jordan Wicks, Hayden Wesneski, and Ben Brown will compete for the fifth spot in the rotation. Additionally, a wave of top prospects—Matt Shaw (ranked 22nd), Owen Caissie (33rd), Moises Ballesteros (41st), Kevin Alcantara (69th), and Cam Smith (99th)—will be pushing for roster spots.

This mix of departures and emerging talent gives the Cubs’ front office several options for shaping the team’s future. However, based on the club’s history, certain choices seem more probable than others.

Tapping An Elite Free Agent Class

Cubs’ $40 million manager Craig Counsell has recently issued a challenge to the entire organization. He is expected to meet with President of Baseball Operations Jed Hoyer this offseason, with discussions potentially focusing on acquiring a top-tier starter. This could involve exploring a promising free-agent market.

Notable options include Braves lefty Max Fried (71 wins and 3 Gold Gloves since 2019), Orioles ace Corbin Burnes (15-9), Giants lefty Blake Snell (2-0 with a 1.03 ERA and a no-hitter since July 9), Padres lefty Tanner Scott (9-6 with a 1.75 ERA), and Dodgers righty Jack Flaherty (13-7).

However, Cubs ownership has historically been reluctant to spend heavily on high-caliber pitchers, often preferring to develop talent internally.

From Japan, With Love

Another potential option for the Cubs could be targeting the Japanese pro league for a quality pitcher. Roki Sasaki, 23, stands out as a strong candidate, offering top-tier talent at a relatively affordable price due to MLB’s international player contract rules.

Under these rules, contracts for players under 25 with less than six years of experience in foreign major leagues are capped. Sasaki, who has posted an impressive 1.95 ERA over four seasons with the Chiba Lotte Marines, could be a realistic and cost-effective option for the Cubs.

Bringing Up Young Arms

Wicks, Brown, and Wesneski each displayed progress this season, but injuries and inconsistency prevented them from securing a spot in the Cubs’ rotation. Veteran Kyle Hendricks ended up making most of the starts in the fifth spot. If Wicks, 25, can regain his form next season, he would provide the Cubs’ rotation with another left-handed option.

Barring another setback from injury, the Cubs’ number two prospect Cade Horton will challenge for the spot in the spring of 2025. Other likely pitching candidates include Jack Neely (#18), and Michael Arias (#19).

A Talent for Talent Trade

The Cubs’ farm system is rich in talent at both infield and outfield positions, but many of those spots on the major league roster are already secured by players with solid contracts or strong performances. This creates a challenge for prospects like outfielders Owen Caissie and Kevin Alcantara, and infielder Matt Shaw, as they may struggle to find playing time.

Cubs management understands they can’t hold onto prospects indefinitely, making a trade likely. This could open the door to acquiring a quality starting pitcher. While top prospects alone may not be enough to secure elite arms like Corbin Burnes or Jack Flaherty, they could be enough to bring in veterans like Blake Snell or Max Fried. Whether it’s landing an ace or making other key moves, the Cubs are in a prime position to make the deals necessary to elevate their competitiveness next season.

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