The Chicago Cubs’ starting rotation for the 2025 season showcases a blend of experienced and emerging pitchers. Leading the staff are left-handers Shota Imanaga and Justin Steele. Imanaga had an impressive rookie season in 2024, achieving a 15-3 record with a 2.91 ERA and earning an All-Star selection. Steele continued his consistent performance, posting a 3.07 ERA over 24 starts.
Right-hander Jameson Taillon adds veteran depth to the rotation. In 2024, he recorded a 12-8 record with a 3.27 ERA across 28 starts, marking one of his best seasons.
The Cubs further strengthened their pitching staff by signing veteran left-hander Matthew Boyd to a two-year, $29 million contract. Boyd returned from Tommy John surgery in 2024 and posted a 2.28 ERA over 11 starts with Cleveland, including a strong postseason performance.
For the fifth starter role, right-hander Javier Assad is a leading candidate. Assad transitioned to a starting role in 2024, finishing with a 7-6 record and a 3.73 ERA. His ability to generate ground balls and limit home runs makes him a reliable option.
Additional depth options include right-handers Colin Rea, Ben Brown, and Jordan Wicks. Rea, who joined the Cubs on a one-year deal, worked 167 2/3 innings for the Brewers in 2024 and is familiar with manager Craig Counsell from their time in Milwaukee. Brown and Wicks, both promising young arms, offer potential impact if they can maintain health and consistency.
The Chicago Cubs have been active in trade discussions to acquire a dominant right-handed starting pitcher to balance their left-handed-heavy rotation. Recent reports indicate that the Cubs are focusing on bolstering their pitching staff after trading outfielder Cody Bellinger. They have shown interest in several pitchers, including:
- Dylan Cease: The Cubs are considered a “team to watch” in the trade market for Cease, who is currently with the San Diego Padres. Cease, originally drafted by the Cubs in 2014, posted a 3.47 ERA with 224 strikeouts in 189.1 innings last season. Acquiring him would provide a proven frontline starter to pair with Shōta Imanaga.
- Jesús Luzardo: The Cubs have been in talks with the Miami Marlins about acquiring left-handed starter Luzardo, who struck out 208 batters in 178 2/3 innings in 2023. However, adding another lefty to the rotation may not address the need for a right-handed starter.
- Luis Castillo: Reports indicate that the Cubs have shown interest in Mariners right-hander Castillo, who is owed $68.25 million over the next three years. Acquiring Castillo would provide a dependable right-handed ace to balance the rotation.
In a recent trade proposal by Athlon Sports, the Chicago Cubs are suggested to trade for right-handed pitcher Dylan Cease from the San Diego Padres. Cease, who has been a consistent subject of trade rumors, posted a 3.47 ERA with 224 strikeouts in 189.1 innings last season. Acquiring him would provide the Cubs with a proven frontline starter to pair with Shōta Imanaga.
This proposal highlights the Cubs’ ongoing efforts to strengthen their starting rotation and achieve a better balance between left- and right-handed pitchers as they prepare for the upcoming season.
In a recent trade proposal, the Chicago Cubs are considering sending right-handed starter Jameson Taillon to the New York Yankees. In return, the Cubs would receive reliever Ian Hamilton and pitching prospect Will Warren. This move aims to bolster the Yankees’ starting rotation depth while providing the Cubs with bullpen support and a promising young arm.
Taillon, who previously pitched for the Yankees before joining the Cubs, has a career record of 51-35 with a 3.84 ERA over seven seasons. Hamilton, a right-handed reliever, posted a 3.62 ERA over 32 appearances last season, and Warren, a 24-year-old prospect, recorded a 3.15 ERA with 140 strikeouts in Double-A.
The New York Yankees are facing significant challenges in their starting rotation as they approach the 2025 MLB season. Ace pitcher Gerrit Cole underwent Tommy John surgery earlier this month and is expected to miss the entire season. Additionally, reigning American League Rookie of the Year Luis Gil has been diagnosed with a high-grade right lat strain, sidelining him for at least six weeks before he can resume throwing.
In response to these setbacks, the Yankees have signed veteran left-hander Ryan Yarbrough to a one-year contract worth $2 million, with up to $500,000 in incentives. Yarbrough, 33, pitched exclusively in relief last season for the Los Angeles Dodgers and Toronto Blue Jays, achieving a 3.19 ERA over 98 2/3 innings in 44 games.
These injuries have prompted the Yankees to explore various roster adjustments to maintain competitiveness in the upcoming season.
Acquiring veteran right-hander Jameson Taillon would significantly bolster the New York Yankees’ starting rotation, especially in light of recent injuries. With ace Gerrit Cole sidelined for the 2025 season due to Tommy John surgery, the Yankees’ rotation depth has been compromised.
Currently, the Yankees’ right-handed starter options include Marcus Stroman, Carlos Carrasco, and Clarke Schmidt. Stroman has been solidifying his role, preparing for his final spring training start before the regular season. Carrasco and Schmidt provide additional depth but have had varying levels of consistency.
Taillon, who previously pitched for the Yankees after being acquired from the Pittsburgh Pirates in 2021, has a track record of resilience and performance. His experience and familiarity with the organization could make him a valuable asset to the rotation if a trade were to occur.
Jameson Taillon’s performance has evolved over recent seasons, reflecting his adaptability and resilience on the mound.
2024 Season with the Chicago Cubs:
In 2024, Taillon delivered a strong performance for the Chicago Cubs, starting 28 games and achieving a 3.27 ERA over 165.1 innings. Notably, on September 28, he pitched seven scoreless innings against the Cincinnati Reds, leading the Cubs to a 1-0 victory.
A significant factor in Taillon’s success was his strategic shift to increase the use of his cutter, throwing it 25.1% of the time compared to 11.3% in 2022. This adjustment diversified his pitching arsenal and leveraged the Cubs’ defensive strengths. Additionally, his walk rate was impressively low at 4.9%, placing him in the top seven percent in the league.
Tenure with the New York Yankees (2021–2022):
Prior to joining the Cubs, Taillon pitched for the New York Yankees during the 2021 and 2022 seasons. In 2021, he recorded an 8-6 record with a 4.30 ERA over 29 starts, accumulating 140 strikeouts in 144.1 innings. A highlight of his tenure was being named the American League Pitcher of the Month in July 2021, posting a 1.16 ERA during that period.
In 2022, Taillon continued to be a reliable presence in the Yankees’ rotation. On June 2, he pitched seven perfect innings against the Los Angeles Angels before surrendering a hit in the eighth inning.
Overall, Taillon’s journey reflects his ability to adapt and perform across different teams and seasons, contributing significantly to his respective clubs’ pitching staffs.
Will Warren, currently ranked as the New York Yankees’ fifth-best prospect, has shown both promise and areas for development in his recent performances. After a challenging MLB debut in 2024, where he recorded a 10.32 ERA, Warren demonstrated significant improvement during the 2025 spring training. He posted a 4.19 ERA with 19 strikeouts over 19 innings, earning him the role of the Yankees’ No. 4 starter for the upcoming season.
In a proposed trade scenario, Warren would join the Chicago Cubs, providing him with an opportunity to further develop without the immediate pressure of starting in the major leagues. This environment could be conducive to refining his skills and building confidence for future contributions at the MLB level.
Acquiring Ian Hamilton could provide a significant boost to the Chicago Cubs’ bullpen, which is currently facing several uncertainties as the regular season approaches. Hamilton, a right-handed reliever, posted a 3.82 ERA over 37.2 innings with the New York Yankees in the 2024 season.
The Cubs’ bullpen has experienced challenges during Spring Training, with recent performances highlighting areas of concern. In a recent game against the Atlanta Braves, multiple relievers struggled, including Ryan Pressly and Porter Hodge. Ryan Brasier, in particular, allowed four runs on four hits in just one-third of an inning, placing his roster spot in jeopardy.
Currently, the Cubs’ bullpen options include pitchers such as Ryan Brasier, Ben Brown, Porter Hodge, Julian Merryweather, Tyson Miller, Nate Pearson, Ryan Pressly, and Caleb Thielbar. Notably, Thielbar is the only left-handed pitcher among them, which may prompt the Cubs to seek additional left-handed options or right-handers with effective splits against left-handed hitters.
Integrating a pitcher like Hamilton, who has demonstrated reliability and effectiveness, could help stabilize the bullpen and address some of these concerns as the Cubs prepare for the upcoming season.
