Andy Pettitte: Three Years with the Astros that Changed Yankees’ History

The best pitcher in New York Yankees’ history was Whitey Ford. The Yankees’ little gamecock won 236 games during his illustrious career.

Andy Pettitte finished his career with 240 wins. Pettitte will always be identified as a Yankee, but the three seasons he spent with the Houston Astros cost him the chance to pass Ford as the Yankees’ all-time leader in wins.

We will never know if Pettitte would have remained with the Yankees when he became a free agent following the 2003 season, which was one of his best, if the Yankees had shown him more respect.

Pettitte won 21 games and did his best to prevent the Yankees from losing the 2003 World Series.

On Nov. 5, 2003, general manager Brian Cashman announced that the Yankees would allow Pettitte to test the free agent market. Despite the fact that Pettitte had not formally filed for free agency, Cashman did present him with any offers..

Once again, the son of a Kentucky horse trainer who was friends with George Steinbrenner demonstrated his acumen when he told reporters that he was not concerned by the presence of the Houston Astros in negotiations.

“You expect to have a competition on your hands when a player of Andy’s ability is available. We’d love to keep Andy. We’ll have out discussion, put our best foot forward and hope for the best.”

One might ask why Mr. Cashman didn’t make an offer when only the Yankees were allowed to negotiate with Mr. Pettitte.

After the World Series, future Hall of Fame manager Joe Torre told Pettitte to do what was best for his family. The Yankee left-hander said that he would call Torre. He never did.

A few days after he filed for free agency, Pettitte passed a physical for the Astros. On Dec. 16, he signed a three-year, $31.5 million contract with the Astros. The fact that Pettitte would be close to his family played a major role in his decision.

“He’s one of the special ones,” Brian Cashman stated. In an attempt to fill the void, Cashman made a deal with the Los Angeles Dodgers to obtain Kevin Brown. What a move.

In his three seasons with the Astros, Pettitte won 37 games. He was injured much of the 2004 season, winning only six times, but he won 17 games in 2005 and 14 his last season with the Astros.

Yankees’ history might have been different if they had retained Pettitte.

There was no way Pettitte could have helped the Yankees in the 2004 playoffs since his season ended in August when he had elbow surgery, but let’s examine the third game of the first playoff round in 2005.

The Yankees scored seven runs against the Anaheim Angels but lost 11-7. Aaron Small was their starting pitcher.

Does anyone think seven runs might have been enough if Andy Pettitte had started for the Yankees? Since the Angels won the series, three games to two, Pettitte might have led the Yankees into the next playoff round.

If Pettitte had remained with the Yankees, he would have eclipsed Whitey Ford’s 236 wins. The fans would not have loved or respected him more, but it would have been nice for him if he had the record.

From a purely baseball perspective, both the Yankees and Pettitte were hurt when he left. What a shame.


Kepner, Tyler. “Cashman Allows Pettitte to Test Free-Agent Market.” New York Times. 5 Nov 2003. p. D2.

Kepner. Tyler. “Yankees Lose Part of Their Core As Pettitte Signs With Astros.” New York Times. 12 Dec. 2003. p.A1.