![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://cdn.bleacherreport.net/images_root/slides/photos/000/693/350/100073658_original.jpg?1296779342)
Andy Pettitte Retires: 10 Pitchers New York Yankees Will Look To
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://static01.nyt.com/images/2013/09/29/sports/sub-jp-yankees/sub-jp-yankees-articleLarge.jpg?quality=75&auto=webp&disable=upscale)
With a Win, the Ending to Pettitte's Illustrious Career Is
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://cdn.bleacherreport.net/images_root/slides/photos/000/692/449/2650368_original.jpg?1296763072)
Andy Pettitte Retires: The 10 'Most Clutch' Performances of His
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://lookaside.fbsbx.com/lookaside/crawler/media/?media_id=1948826845300065&get_thumbnail=1)
Andy Pettitte's Greatest Moments
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://i.ytimg.com/vi/ucA9pnHB-7w/hq720.jpg?sqp=-oaymwEhCK4FEIIDSFryq4qpAxMIARUAAAAAGAElAADIQj0AgKJD&rs=AOn4CLAbIaNS8bH9YN1yX-uoPp-gy6JkIg)
Andy Pettitte wins his 200th game as a Yankee
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://lookaside.fbsbx.com/lookaside/crawler/media/?media_id=205150715096721&get_thumbnail=1)
Andy Pettitte's Greatest Moments
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://i.ytimg.com/vi/wm4wFXK2YGs/maxresdefault.jpg)
Andy Pettitte returning to the New York Yankess
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](http://bronxpinstripes.com/wp-content/uploads/2015/08/51710167.jpg)
Pettitte's 5 Best Playoff Wins
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://cdn.bleacherreport.net/images_root/slides/photos/000/692/646/72454771_original.jpg?1296773264)
Andy Pettitte Retires: The 10 'Most Clutch' Performances of His
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://cdn.bleacherreport.net/images_root/slides/photos/000/693/368/102922515_original.jpg?1296779619)
Andy Pettitte Retires: 10 Pitchers New York Yankees Will Look To
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://cdn.bleacherreport.net/images_root/slides/photos/000/693/690/53051281_original.jpg?1296787562)
Yankees' Andy Pettitte Announces Retirement: A 5-Time World
![Generations collide: Andy Pettitte wins 250th, watches Yanks draft](https://i.ytimg.com/vi/YUPHEs9QbLg/hqdefault.jpg)
Yankeeography: Andy Pettitte