33. Gerrit Cole

Gerrit Cole joined the Houston organization in January 2018 via a blockbuster trade with the Pittsburgh Pirates, a move that sent four players—including Joe Musgrove and Colin Moran to the National League. While Cole was a former All-Star in Pittsburgh, he arrived in the Space City with a reputation as a talent waiting to be fully unlocked. For two historic seasons in a Houston uniform, he transitioned from a solid starter into a tactical nightmare for hitters, proving that a high-velocity arm paired with modernized pitch sequencing could dominate.

Upon his arrival in 2018, he demonstrated a specialized ability to miss bats at a historic rate, leading the American League in strikeouts per nine innings (12.4). He surged to a 15-5 record and a 2.88 ERA in his debut year, finishing fifth in the Cy Young voting and providing the high-frequency production needed to push the Astros back to the ALCS. This period of rapid growth served as the essential lead-in to his 2019 campaign, showing that when a pitcher pairs a triple-digit heater with an elite spin rate, he can become a foundational force that alters the geometry of the strike zone.

Cole’s journey reached a historic peak of efficiency and outlier value during the 2019 season. That summer, he evolved into a statistical titan, leading the American League in ERA (2.50), strikeouts (326), and ERA+ (186). He demonstrated a specialized ability to carry a workload in the modern game, recording a 20-5 record and a microscopic 0.895 WHIP. He showed the organization that he was a big-game performer by navigating the 2019 postseason with a 4-1 record and a 1.72 ERA, nearly single-handedly propelling the club to within one game of a second World Series title. Though he narrowly finished as the runner-up to teammate Justin Verlander for the Cy Young Award, his season remains a benchmark for single-season greatness in the 21st century.

He departed following the 2019 World Series, as Cole signed a landmark nine-year contract with the New York Yankees.  In Houston, Cole compiled a 35-10 record, 602 strikeouts, and a 2.68 ERA.