Andy Pettitte retired from Major League Baseball with 256 regular season wins, 219 of those with the Yankees. In the postseason, he secured 19 more victories while pitching 276.2 innings of playoff baseball. However, as the Trade Deadline loomed in 1999, many doubted that Pettitte’s career would reach such heights.
To put it plainly, Pettitte had a rough year in 1999. Compounding the issue, he had reached his arbitration years and was poised to earn a significant salary, projected to exceed $7 million for 2000, according to Buster Olney. With just three days remaining before the deadline, Pettitte took the mound against the White Sox with a 5.57 ERA.
Teams like Seattle, Cincinnati, Houston, and Detroit, along with others, were eyeing the 27-year-old with interest, particularly the Phillies, who came close to acquiring him. Unfortunately, Pettitte had another poor outing, and the Yankees suffered a lopsided loss to the struggling White Sox.
