Roy Halladay, a two-time Cy Young Award-winning pitcher who spent 16 years with Toronto and Philadelphia died when the plane he was piloting crashed into the Gulf of Mexico on Tuesday. He was 40.

Cardinal fans will remember his pitching duel with his good buddy Chris Carpenter in Game Five of the NLDS when his Philllies lost to the Cardinals 1-0, back in 2011.  In that game, Halladay pitched eight innings and allowed just six hits and a walk while striking out seven but came up on the losing end.

Carpenter who came up through the Blue Jays system with Halladay released a statement.

“I love him and Brandy and I am so sad for her and the kids! We grew up together. Went through good and bad times together. He was an amazing pitcher, competitor, teammate and friend. I have so many memories with him and his family. I will miss him”

Halladay was also the starting pitcher for the National League in the 2009 All-Star Game at Busch Stadium.