Major League Baseball history is filled with trades that haunt teams for years, and several deals from the past six years stand out as particularly regrettable. Notable trades between January 1, 2017, and December 31, 2023, resulted in teams losing players who could still be under their control in 2025. Not included are trades that involved players who had already become free agents or were on the verge of free agency.

The Chicago Cubs’ decision to send Dylan Cease and Eloy Jiménez to the Chicago White Sox for Jose Quintana exemplifies a painful trade. While Quintana was expected to be a top pitcher, he failed to deliver, while Cease has developed into a Cy Young contender.

Another disastrous trade involved the St. Louis Cardinals dealing Sandy Alcántara and Zac Gallen to the Miami Marlins for Marcell Ozuna. Alcántara has become an elite pitcher, making this trade particularly stinging for the Cardinals, especially in light of their recent struggles.

Walker Buehler's move from the Los Angeles Dodgers to the Boston Red Sox marks a pivotal shift in his career. The right-handed pitcher, who secured the World Series title for the Dodgers against the New York Yankees, now aims to contribute significantly to the Red Sox and help them ascend in the American League East. Buehler's free agency followed a challenging recovery from Tommy John surgery, which kept him sidelined for nearly two years.

His 2024 season with the Dodgers was marked by a 5.38 ERA across 16 games, yet he found his form in the playoffs with 10 scoreless innings, including a flawless ninth inning in the World Series. This inconsistency led to a one-year, $21.05 million deal with Boston as he strives to prove his value.

The Boston Red Sox have engaged in preliminary contract extension discussions with left-hander Garrett Crochet, acquired from the Chicago White Sox during the offseason. While the talks are in early stages, no agreement appears imminent. Crochet remains under contract through the 2026 season, alleviating immediate pressure for the Red Sox. However, securing a deal before he pitches this season could yield a more favorable contract.

In his first full season as a starter in 2024, Crochet recorded a 6-12 record with a 3.58 ERA, striking out 209 batters in 146 innings, earning him an All-Star selection. After a stint in the bullpen since his debut in 2020, he has faced injuries, particularly from Tommy John surgery. The Red Sox aim to bolster their rotation, featuring Crochet alongside Walker Buehler, Brayan Bello, Tanner Houck, and Lucas Giolito.

The Boston Red Sox are exploring the possibility of implementing a six-man rotation for the 2025 season, a significant shift aimed at enhancing their starting pitching depth. Chief Baseball Officer Craig Breslow has expressed openness to various solutions following the acquisition of pitcher Garrett Crochet and the signing of free agents Patrick Sandoval and Walker Buehler. Breslow emphasized the necessity of having more than five dependable starters, especially given the team's struggles in the previous season when injuries and trades significantly weakened their pitching staff.

Last season, the Red Sox faced a major setback when they lost potential aces Chris Sale and Lucas Giolito, leading to a lack of depth in their starting rotation. This resulted in a disappointing second half of the season, ultimately keeping the team out of playoff contention for the third consecutive year. In response, Breslow has taken proactive steps to bolster the rotation by bringing in new talent, including the hard-throwing Crochet, who had a challenging season with the Chicago White Sox, and Buehler, a two-time All-Star recovering from surgery.

Breslow highlighted the potential of these new additions to elevate the team's rotation from good to elite. Buehler's postseason performance, despite a tough regular season, showcased his capability to deliver under pressure, while Sandoval is expected to contribute following his recovery. Alongside these newcomers, the Red Sox have a promising group of pitchers, including Giolito and others, giving Breslow confidence in their depth. He also mentioned a focus on balancing the team's left-handed hitters and addressing the bullpen's needs. Notably, Breslow confirmed that first baseman Triston Casas is not on the trading block, as they are eager for him to return to full health.