16. John Lackey

John Lackey joined the Angels organization as a second-round pick in 1999 out of Grayson County College, a big right-hander who would quickly become the backbone of the rotation. He reached the major leagues in 2002 and immediately made history as a rookie, where in a winner-take-all Game 7 against the Giants, he became the first rookie in 93 years to start and win a World Series clincher, tossing five innings of one-run ball.

Between 2003 and 2006, he bridged the gap to his elite 19-win peak by proving he could handle a heavy workload year after year. He recorded at least 14 wins in three of those four seasons and consistently sat near the top of the league leaderboard in starts. 

In 2005, he reached the 199-strikeout mark, a career-best at the time, while posting a 3.44 ERA. He followed that with another 190 strikeouts in 2006, providing the steady production required to lead the staff through the transition following the departures of veteran arms like Jarrod Washburn. This stretch of reliable, high-volume pitching served as the essential lead-in to his 2007 ERA title and cemented his status as the unquestioned ace of the staff.

John Lackey’s departure from Anaheim following the 2009 season was primarily a matter of the organization’s hesitation to match the market’s valuation of his longevity. While Lackey had been the anchor of the staff for nearly a decade, the Angels management grew wary of his long-term durability after he missed the first six weeks of both the 2008 and 2009 seasons due to recurring elbow and forearm issues.

The tension began to surface during spring training in 2009 when the club offered Lackey a three-year extension worth approximately $40 million. Lackey, who had previously signed a team-friendly deal to help the club remain competitive, viewed the offer as a sign that the front office did not see him as a top-tier ace. He made it clear that he would not accept another hometown discount and entered free agency seeking a contract that reflected his status as a workhorse.

The Boston Red Sox eventually stepped in with a five-year, $82.5 million contract, an offer that included both more money and more guaranteed years than the Angels were willing to provide. With the Angels, Lackey compiled a 102-71 record, 1,201 strikeouts, and the 2002 World Series Game 7 victory.