He resigned as general manager of the Twins on October 1, 2007, but returned to his former post on November 7, 2011, until being relieved of his duties on July 18, 2016.

His playing career started with promise: Ryan posted a 10–0 record and 1.70 ERA in 43 games at Class A Wisconsin Rapids in 1973.

After graduating from the University of Wisconsin–Madison in 1979, with a degree in physical education,[4] Ryan quickly earned respect as an evaluator of talent in baseball.

Ryan's organization relies heavily on constant scouting and analysis of every player in major and minor league baseball.

Things started looking up for Ryan only a couple of months later, when he traded veteran Dave Hollins to the Seattle Mariners for a player to be named later.

In 1998, he sent the disgruntled Chuck Knoblauch to the New York Yankees for four players, including two future All-Stars: shortstop Cristian Guzman and pitcher Eric Milton.

At the end of the year, he traded for future Cy Young Award winner Johan Santana, who was picked up in the Rule 5 Draft by the Florida Marlins from the Houston Astros.

His most recent trades affecting the current team were in December 2005, when he received second baseman Luis Castillo from the Florida Marlins for two minor leaguers.

[7] He was replaced by assistant general manager Bill Smith, but remained in the Twins organization as a senior adviser.

[7] On November 7, 2011, Twins owner Jim Pohlad fired Smith after a 99-loss season - the first time that the Twins had fired a general manager since relocating from Washington, D.C. Ryan, who had remained with the team in a consultant role since stepping down as GM after the 2007 season, returned to the job, officially on an interim basis.

On October 6, 2012, Ryan announced that he had removed the "interim" from his title and would return as Minnesota's long-term general manager for the 2013 season.