[1] After going unselected in the Major League Baseball (MLB) draft out of high school, Ryan enrolled at the Centenary College of Louisiana and played for the Gentlemen.

As a sophomore pitcher, Ryan threw seven complete games while racking up 100.2 innings pitched for the season.

[2] When Ryan decided to transfer to the University of Louisiana at Lafayette in the fall of 1996, the team used him as a relief pitcher, filling the role of their spot starter, in addition to playing outfield and first base.

[3] He quickly became one of UL Lafayette's best hitters, so the team moved Ryan into their starting first base position midway through the season.

[6] He earned yet another promotion before the season ended to the Chattanooga Lookouts of the Southern League finishing the year with a 2.06 ERA in 33 games with 10 saves.

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.

[10] In 2005, Ryan had a spectacular season as closer for Baltimore, going 1–4 with a 2.43 ERA while converting 36 of 41 save opportunities in 69 relief appearances.

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 five-year, $47 million contract with the Toronto Blue Jays on November 28, 2005.

[12] At the time, that was the largest contract for a reliever in Major League Baseball history, surpassing Mariano Rivera's four-year, $40 million deal with the Yankees from 2001 to 2004.

During the 2006 All-Star Game held on July 10 in Pittsburgh, Pennsylvania, Ryan pitched the scoreless eighth inning and earned the win for the American League.

[11] On May 10, 2007, the Blue Jays announced that Ryan underwent Tommy John surgery in his left elbow and would be out for the remainder of the 2007 season.

[17] Despite his arm not being fully healed and his slider's reduced effectiveness, he still managed to save an impressive 32 games for the Jays, placing sixth in the American League.

On April 23, Ryan was placed on the 15-day DL with problems in his throwing shoulder, more specifically a strained trapezius muscle.