27. Dallas Keuchel

Dallas Keuchel joined the Houston organization as a seventh-round selection in the 2009 draft out of the University of Arkansas, a left-hander whose path to the big leagues was defined by a rapid three-year climb through the minors alongside fellow prospects Jose Altuve and J.D. Martinez. After debuting in 2012, he transitioned from a struggling young starter into the definitive ground-ball specialist of the American League, providing a specialized sinking fastball that few hitters could elevate.

The climb toward Keuchel’s historic 2015 peak was a study in high-frequency improvement and tactical refinement. After enduring a difficult introduction to the majors, he evolved into a frontline starter by 2014, earning his first of five career Gold Glove Awards for his elite defensive reliability. This period of rapid growth served as the essential lead-in to his most dominant run, showing that when a pitcher pairs a pinpoint changeup with focused intensity at the bottom of the strike zone, he can become a perennial award contender. By 2015, he had officially seized the role of the league’s premier southpaw, becoming a primary catalyst for the Astros' first postseason appearance in a decade.

That summer, he demonstrated a specialized ability to dismantle opposing lineups, recording a 20-8 record and a 2.48 ERA while leading the American League in wins and innings pitched. He showed the organization that he was a foundational winner, winning the Cy Young Award and finishing fifth in the MVP voting, a testament to his status as a certified ace. He possessed a rare, durable quality that allowed him to toss three complete games and two shutouts, providing the steady-state production required to turn Houston into a powerhouse. While he battled through injuries in the following years, he returned to All-Star form in 2017, posting a 14-5 record and a 2.90 ERA to help secure the franchise’s first-ever World Series title.

After amassing a 76-63 record and 945 strikeouts while wearing the Houston colors, Keuchel rejected a qualifying offer from the club, leading to a long wait on the open market due to draft-pick compensation rules. He eventually signed a one-year deal with the Atlanta Braves in June 2019.