His father was an infielder for Loyola Marymount University and holds the school's single-season record for the most hits with a wooden bat.

[citation needed] In 2003, Ryan entered the MLB amateur draft and was selected in the seventh round (215th overall) by the St. Louis Cardinals.

In 2006, Ryan suffered a wrist injury in spring training limiting him to 28 games spread among four stops in the minors.

Ryan was originally called up on and made his major league debut for the Cardinals on June 2, 2007, against the Houston Astros.

His first major league home run was a game-winner in the top of the 11th inning off of Scott Schoeneweis of the New York Mets on June 26, 2007.

On August 20, 2009, in the second inning of the Cardinals and Padres Game, Ryan hit his first career grand slam off of San Diego pitcher Tim Stauffer.

By the end of the 2009 regular season, Ryan's defense at shortstop had been recognized as a major factor in the Cardinals' divisional title.

However, in February 2010, he underwent a procedure to debride dead tissue from his right wrist performed by Dr. Steven Shin in Los Angeles.

[5] On July 26, 2011, Ryan broke up CC Sabathia's bid for a perfect game with a base hit with one out in the seventh inning.

On August 2, 2011, during a game against the Oakland Athletics, alert play by Ryan led to the unusual result of his reaching third on an infield hit.

[7] On June 8, he entered as a defensive replacement in the ninth inning of the Mariners' combined no-hitter against the Los Angeles Dodgers and made one of the game's closest putouts by throwing Dee Gordon out at first base.

As of May 2, 2014, he was on the 15-day disabled list with cervical spine nerve damage and was playing rehab games at AA Trenton.

[13] On December 17, 2015, the Yankees officially announced that Ryan had been the player to be named later in their trade with the Chicago Cubs for shortstop Starlin Castro.

[15] On February 2, 2016, the Washington Nationals signed Ryan to a minor league contract with an invitation to spring training.

On December 19, 2016, Ryan signed a minor league deal with the Detroit Tigers, worth $625,000, which included an invite to spring training.

[20] He spent the 2017 season with the Triple–A Toledo Mud Hens, playing in 112 games and hitting .236/.324/.326 with 4 home runs and 28 RBI.