Five-time World Series winner Andy Pettitte, one of baseball's most accomplished pitchers and a man whose reputation took a hit when he admitted taking a performance-enhancing drug, is about to call it a career.
Pettitte, 38, will announce his retirement Friday, according to the New York Yankees, with whom he won all his World Series titles and played 13 of his 16 Major League seasons.
The left-handed Louisiana native and Texas resident will finish his career with a 240-138 record and 3.88 ERA in 479 starts with the Yankees (1995-2003 and 2007-10) and the Houston Astros (2004-2006).
He is one of just 26 pitchers to complete his career 100 or more games over .500. Of the 19 Hall of Fame-eligible pitchers who have reached that plateau, only one, "Parisian" Bob Caruthers, who played from 1884 to 1892, is not in the Baseball Hall of Fame, according to the Yankees.
Pettitte also is the all-time winningest pitcher in postseason history, going 19-10 with a 3.83 ERA in 42 starts, according to the Yankees. He won World Series titles with the Yankees in 1996, 1998, 1999, 2000 and 2009. He appeared in the World Series two other times as a Yankee and once as an Astro, in 2005.
Pettitte was named in a 2007 report - written by a group led by former Sen. George Mitchell - on illegal use of performance-enhancing drugs in baseball. The report became the basis of a hearing two months later by the House Committee on Oversight and Government.
Pettitte has admitted using growth hormone twice, in 2002 and 2004.
He also has been a key figure in a case against former pitcher and teammate Roger Clemens. Clemens is charged with obstruction of justice, perjury and making false statements on suspicion of lying to Congress about whether Clemens used performance enhancing drugs.
In a sworn statement to the House committee, Pettitte said Clemens admitted using the hormone during a conversation the two had in 1999 or 2000. Clemens has said that Pettitte misheard the conversation.
The two men were close friends before falling out as a result of the federal investigation. Clemens' trial is scheduled for July, and prosecutors could call Pettitte to testify.
On SI.com, Tom Verducci writes of Pettitte's joy for the game and how his devotion to his team made for a successful career, and Cliff Corcoran writes about the difficult task the Yankees have in trying to replace Pettitte in the starting rotation.
CNN's Paul Courson contributed to this report.