On May 16, 2007, Casey was voted in 2007 as "the friendliest player in baseball" by fellow players in a Sports Illustrated poll. He garnered 46% of the vote with the second place vote being split between Jim Thome and Mike Sweeney with only 7% each. Casey was also regarded as among the slowest-running players in the game, grounding into 27 double plays in the 2005 season. This tied him with A. J. Pierzynski for the record of most grounding in double plays by a National League left-handed batter in a season. Pittsburgh Pirates On December 8, 2005, Casey was traded to his hometown Pittsburgh Pirates for left-handed pitcher Dave Williams. On April 14, 2006, Casey left a game against the Chicago Cubs after suffering two fractures of the transverse process in his lower left back. He was placed on the disabled list on April 15. After a rehab assignment with the Altoona Curve, Casey returned to the Pirates lineup. During an injury plagued 59-game tenure for the Pirates, Casey hit .296 with three home runs and 29 RBI. Detroit Tigers On July 31, 2006, Casey was traded to the Detroit Tigers for minor league pitcher Brian Rogers. During the 2006 American League Championship Series against the Oakland Athletics, he partially tore his left calf muscle in Game 1. After coming back from his torn calf in Game 2 of the World Series, Casey became the hottest hitter for the Tigers, belting two home runs and batting .432 in five games. His .432 batting average was one of the best in Tigers' postseason history. Casey has been active in Big Brothers and Make-A-Wish Foundation, as well as the "Casey's Crew" program, where he provided free high-priced tickets to disadvantaged youth. Casey credits his Christian upbringing in Pittsburgh's affluent Upper St. Clair suburb for his generosity. After being told by Dave Dombrowski and Jim Leyland that he would not be re-signed, Casey still praised Mike Ilitch, Dombrowski, and Jim Leyland for giving him the opportunity to come play for Detroit. Casey said "They let me know. I've had a great time with this team, the greatest year and a half of my career. It was great. But I understand the situation." Boston Red Sox On February 5, 2008, the Boston Red Sox announced they had signed Casey to a one-year deal. On April 9, 2008, Red Sox third baseman Mike Lowell