As announced yesterday, Yankees pitcher Andy Pettitte will once again be retiring. I imagine this time it is for good. I watched a few of his starts this season and no matter if he was good or bad, getting outs seemed like a bit of a struggle for him this season and while he may have shown some age, he pitched some good games for a team that is all but certain to spend October on the golf course.
Pettitte won many big games for the Yankees over the years but he wasn't always so well thought off in the Yankees organization. He had had a really tough first half in 1999 which irritated George Steinbrenner and sparked a debate within the organization on if he should be traded. The 1999 Phillies were in such of pitching at the deadline and it's unclear who stepped down from the trade that was in place but it seemed possible even probable that Pettitte would be dealt to the Phillies for prospects Reggie Taylor and Adam Eaton.
Obviously this trade never happened. Reggie Taylor turned into a player to be named later in 2002 (Hector Mecado) in a trade to the Reds. Adam Eaton turned into a horrible season of Andy Ashby in 2000 but of course he did return to pitch horribly for the Phillies in their valiant 2007 campaign for the National League East and would eventually win a World Series ring by riding the pine in the 2008 postseason. Andy Pettitte would pitch for three more championship Yankees clubs, makes two more trips to the All Star Game, and became the winningest pitcher in postseason history.
It's always fun to look at what could have been with these trades and what actually was. Sure Pettitte wasn't the greatest pitcher ever but he was a very good pitcher for a very successful franchise and one wonders if Steinbrenner and Brian Cashman had their way in 1999 if the Yankees would be as successful as they were. Either way, it's been a great career for Pettitte and the Phillies made out alright without him in the end too.