signed a three-year contract with the Chicago Cubs and pitched his way to an ERA of 3.38. He was one of the more consistently used relievers on a pitching staff that often struggled. He was used mainly in 7th and 8th inning situations in tandem with Bob Howry with Eyre being used more often in lefty vs. lefty situations. Eyre has noted that Lou Piniella could not remember his name for the longest time and called him "Stevie" for a while, jokingly, even after he learned Scott's real name. According to Cubs play-by-play broadcaster Len Kasper, Piniella has since begun intentionally pronouncing his name "Stevie Aye-er." During a game against the Houston Astros on September 12, , Eyre left the Cubs’ bullpen, and wandered around Minute Maid Park. WGN’s cameras eventually spotted him watching the game through an opening in the stadium’s score board. On June 15, , in a game against the Toronto Blue Jays, Eyre allowed a 1-out sac fly run, ending his streak of 33 consecutive appearances without allowing a run, a Cubs franchise record. Philadelphia Phillies (2008–2009) On August 5, 2008, Eyre was designated for assignment to make room for Kerry Wood, who was coming off the disabled list. He was traded to the Philadelphia Phillies two days later for Brian Schlitter. However, the move allowed Eyre to win his first World Series ring when the Phillies won the 2008 World Series. In November, 2008, following the World Series, Scott re-signed with the Phillies as a free-agent, and was signed through the 2009 season. On November 12, 2009, Eyre was granted free agency. Retirement Eyre announced his retirement from MLB on January 8, 2010. He finished his career with a 28–30 record and a 4.23 ERA in 617 games with five teams across 13 major league seasons. He said that the decision was not because the Phillies declined to offer him a contract for the 2010 season, but that "I had most of this retirement thing planned out ... I think even if [the team] would have offered me a better contract, I still don't think I would have taken it." After his retirement, Eyre began coaching the baseball team at Saint Stephen's Episcopal School in Bradenton, Florida, where his son played as a first baseman and designated hitter. Beginning in 2015, Eyre regularly faced his brother Willie, who became the coach for the rival Canterbury