In a career that has spanned seven years, Ryan has compiled a 16-19 record with 465 strikeouts and a 3.54 ERA in 381 1/3 innings pitched.

Ryan started his career as a left-handed specialist. His inability to command his pitches, combined with a history of difficulty facing right-handed batters, prevented him from acquiring a larger role in the bullpen. However, his eccentric, three-quarter, slingshot-like delivery has made him a dominant force against left-handed batters.

More recently, Ryan has been able to not only control his pitches better, but also add tailing movement to his low-90s fastball. This movement, combined with his already-devastating slider, has helped his success rate against right-handed batters. During his years with Baltimore, he translated this success into a larger role in the Orioles' bullpen. By the middle of 2004, he secured the primary setup role. By the end of the year, he took flamethrower Jorge Julio's job as the closer. The baseball world has also recognized his new-found success, and his abilities as a reliever are widely considered to be among the best in baseball. In 2005, Ryan had a spectacular season as closer for Baltimore, converting 36 of 41 save opportunities and compiling a 2.43 ERA and appearing in the All-Star Game.

Ryan became one of the most coveted free agents in Major League Baseball during the 2005 off-season. After considering an offer to rejoin the Orioles, as well as visiting with other potential suitors such as the Cleveland Indians and New York Yankees, Ryan signed a 5-year, $47-million contract with the Toronto Blue Jays on November 28, 2005. At the time, that was the largest contract for a reliever in Major League Baseball history, surpassing Mariano Rivera's 4-year, $40-million deal with the Yankees from 2001-2004.