About a month ago, I created a GIF retrospective on Mariano Rivera's career, wherein I created or linked to the 42 best GIFs of his Yankee tenure. That task was a bit of an undertaking, and with all due respect, Andy Pettitte's career has not featured as many incredible moments as Mo's career (not many MLB careers even come close to Mo). However, I felt that the ol' southpaw deserved some due, so while there are not 46 GIFs in this post, here is a solid collection of GIFs which chronicle Andy Pettitte's 18 years in baseball.
Early pickoff prowess
In his first playoff game, the rookie Pettitte picked off two Mariners, including the first baseman who would eventually receive approximately 50 of his 107 career pickoffs, Tino Martinez.
The '96 home opener was in the snow, but it didn't faze the 23-year-old Pettitte, who pitched well in a 7-3 win. He went on to finish runner-up for the AL Cy Young Award in '96 as the Yankees won their first AL pennant in 15 years.
World Series hero
Pettitte was awful in the '96 World Series opener against the Braves, but with the series tied at two on the road, he dominated the defending champions with 8 1/3 scoreless innings. Most famously, he worked out of a first and third, no out jam in the sixth on two comebackers. He made almost 500 starts after this, but he was likely never better than he was on this night at Atlanta-Fulton County Stadium's finale.
Swept off their feet
Memories of second-half struggles in '98 were erased on a fantastic night in San Diego, when Pettitte threw 7 1/3 scoreless to finish off the four-game World Series sweep of the Padres. He made Ken Caminiti look so bad that the '96 NL MVP struck out and corkscrewed into the ground.
Andy vs. the lolMets
Pettitte pitched to a 1.98 ERA in two World Series starts against the Mets in the 2000 Subway Series, adding two more playoff pickoffs in the process thanks to Mike Piazza and Kurt Abbott.
The Yankees mistakenly allowed Pettitte to walk as a free agent after 2003, and he spent three years with the Houston Astros. Yankee fans like to forget this period, as Pettitte's former teammates failed to make the World Series each year, and in '05, Pettitte was outstanding in pitching the Astros to their first National League pennant. They were swept by the White Sox in the World Series, but Pettitte left his Game 2 start in the seventh with a 4-2 lead.
Andy at the bat
Andy wasn't much of a hitter during his career, only notching 30 hits* in 261 career plate appearances. However, he made his last playoff hit count, as back with the Yankees in '09, he blooped a game-tying single in Game 3 of the World Series against defending Series MVP Cole Hamels. Even Andy seemed a little shocked by it. The Yankees went on to win the game, 8-5.
*Only somewhat related, but Pettitte hit one homer in his career: a solo shot to right field at Houston's Minute Maid Park off the Dodgers' Chan Ho Park on August 11, 2006. A thousand Internet points to whoever can unearth this video.
Five fingers, five rings
Pitching on just three days' rest for the first time in three years, Pettitte closed out the '09 World Series with 5 2/3 innings of four-hit ball; the Yankees won, 7-3 to make Pettitte and his longtime teammates Derek Jeter, Mariano Rivera, and Jorge Posada champions for the fifth time.
After a year of retirement in 2011, Pettitte came back for two more years beginning with a run to the ALCS with the Yankees in 2012. Although a line drive to the leg limited him to 14 starts on the year including postseason, he pitched to a 2.93 ERA on the year in 89 innings. In the 44th and final playoff start of his career, he limited the powerful Tigers to two runs in 6 2/3 innings. Not bad for a 40-year-old who spent a year and a half away from the game. He finished his 18-year career in 2013 by throwing a complete game five-hitter in his final start.