[2] After the conclusion of his playing career, Ricciardi became a coach in the New York Yankees farm system in the early 1980s before joining the Oakland Athletics organization in 1986 as a minor league instructor and scout.

Ricciardi made his break into the front office in 1996, when he became special assistant to Athletics general manager Sandy Alderson.

Under new general manager Billy Beane, who was hired in 1997 and had been Ricciardi's former teammate with the Little Falls Mets,[3] his role became director of player personnel.

[7] After arriving in Toronto, one of Ricciardi's first deals was to send hard-throwing reliever Billy Koch to the Athletics for third baseman Eric Hinske and pitcher Justin Miller.

Delgado became a free agent in the off-season, and for financial reasons the Blue Jays did not seriously pursue re-signing him; the Florida Marlins eventually inked him to a contract.

Ricciardi's arrival in Toronto had been greeted with great optimism and enthusiasm after the team had suffered through several disappointing seasons.

Ricciardi was given more freedom to move after Blue Jays owner Ted Rogers expanded the team's payroll to $210 million over three years prior to the 2005 season.

[9] While Romero would have modest success, even being named to the 2011 MLB All-Star Game as a Blue Jay before eventually being released by the team, Tulowitzki would have the better career, winning multiple awards with the Colorado Rockies.

Coincidentally, Tulowitzki would join the Blue Jays 10 years later in a trade executed by Riccardi's successor, Alex Anthopoulos.

After the 2005 season (in which the Blue Jays posted an 80–82 record), Ricciardi began working to improve Toronto's pitching, signing free agent starter A. J. Burnett and closer B.J.

The additions paid significant dividends for the team in 2006, as the Blue Jays finished second in the tough American League East with an 87–75 record.

Seeking to upgrade the everyday lineup as well, Ricciardi signed a two-year contract with experienced slugger and designated hitter Frank Thomas.

Ricciardi also signed veteran shortstop Royce Clayton as a "stopgap" measure to shore up the middle infield for the 2007 season.

"[10] Despite the lack of hitting on his 2008 ball club, Ricciardi had assembled one of the more effective pitching staffs in Major League Baseball, bolstered by bullpen pick-ups such as Scott Downs, Brian Tallet, Jesse Carlson, and Shawn Camp.

The day before Blue Jays players had gone public with criticism over Gaston's managing style, and had asked for a meeting with team president Paul Beeston.