With Toronto Blue Jays general manager Alex Anthopoulos’ contract set to expire on October 31, TSN.ca takes a look back at the 38-year-old’s time with the team.

October 3, 2009: Anthopoulos, 32-years-old at the time, is named general manager of the Blue Jays, replacing J.P. Ricciardi. Anthopoulos joined the Blue Jays organization in 2003 as a scouting coordinator.

December 16, 2009: Anthopoulos trades ace Roy Halladay to the Philadelphia Phillies for pitcher Kyle Drabek, catcher Travis d’Arnaud and outfielder Michael Taylor. Taylor was quickly traded to the Oakland Athletics for prospect Brett Wallace.

December 22, 2009: Anthopoulos acquires Brandon Morrow from the Seattle Mariners in exchange for reliever Brandon League and outfielder Johermyn Chavez.

July 14, 2010: Anthopoulos trades shortstop Alex Gonzalez and minor leaguers Tim Collins and Tyler Pastornicky to acquire infielder Yunel Escobar and pitcher Jo-Jo Reyes from the Atlanta Braves.

July 29, 2010: Anthopoulos sends Wallace to the Houston Astros in exchange for centre fielder Anthony Gose.

October 3, 2010: The Blue Jays finish the 2010 season with an 85-77 record, fourth in the American League East – 11 games back of the Tampa Bay Rays.

January 21, 2011: Anthopoulos trades veteran outfielder Vernon Wells to the Los Angeles Angels for catcher Mike Napoli and outfielder Juan Rivera. Napoli was quickly traded to the Texas Rangers for pitcher Frank Francisco. Rivera was dealt to the Los Angeles Dodges for a player to be named later or cash considerations.

Embedded ImageJuly 28, 2011: Anthopoulos ships pitchers Zach Stewart and Jason Frasor to the Chicago White Sox to acquire starter Edwin Jackson and infielder Mark Teahen. Anthopoulos then traded Jackson to the St. Louis Cardinals along with relievers Marc Rzepczynski and Octavio Dotel, outfielder Corey Patterson and three players to be named later or cash for outfielder Colby Rasmus and relievers Brian Tallet, P.J. Walters and Trevor Miller.

August 23, 2011: Infielders Aaron Hill and John McDonald are traded to the Arizona Diamondbacks for Kelly Johnson.

September 28, 2011: The Blue Jays finish the 2011 at 81-81, finishing fourth in the AL East for the second straight year. The team finished 16 games back of the New York Yankees in their division and 10 games back of a wild card spot.

Embedded ImageJune 4, 2012: Anthopoulos selects pitcher Marcus Stroman with the team’s second pick of the first round, 22nd overall. The team used their first pick of the round, 17th overall, on outfielder D.J. Davis.

October 3, 2012: The Blue Jays finish the 2012 season at 73-89, finishing the season fourth in the AL East for the third straight year.

November 8, 2012: Free-agent infielder Maicer Izturis signs a three-year contract with the Blue Jays. Anthopoulos also acquires pitcher Esmil Rogers from the Cleveland Indians for Mike Aviles and Yan Gomes.

November 13, 2012: Anthopoulos makes a blockbuster deal with the Miami Marlins to acquire to four-time All-Star shortstop Jose Reyes, pitchers Mark Buehrle and Josh Johnson, catcher John Buck and Emilio Bonifacio for Escobar, pitcher Henderson Alvarez, catcher Jeff Mathis and four prospects (Andy Hechavarria, Jake Marisnick, Anthony DeSclafani and Justin Nicolino). Toronto also received more than $8 million cash from the Marlins.

November 16, 2012: Free-agent outfielder Melky Cabrera signs a two-year, $16 million contract with the Blue Jays.

November 20, 2012: Anthopoulos hires John Gibbons as manager of the Blue Jays, replacing John Farrell, who left the Jays to manage the Boston Red Sox.

December 17, 2012: Anthopoulos completes his second blockbuster trade in just over a month, acquiring reigning NL Cy Young winner R.A. Dickey from the New York Mets in exchange for d’Arnaud, Buck, pitcher Noah Syndergaard and outfielder Wuilmer Becerra. The Blue Jays also received catchers Josh Thole and Mike Nickeas from the Mets.

September 29, 2013: The Blue Jays finish the season last in the AL East with a 74-88 record.

June 5, 2014: Anthopoulos selects pitcher Jeff Homan and catcher Max Pentecost in the first round of the MLB draft.

September 28, 2014: The Blue Jays finish the 2014 season at 83-79, third in the AL East.

November 18, 2014: Anthopoulos signs catcher Russell Martin to a five-year, $82 million contract.

Embedded ImageNovember 28, 2014: The Blue Jays acquire All-Star third baseman Josh Donaldson from the Oakland Athletics in exchange for third baseman Brett Lawrie, shortstop Franklin Barreto and pitchers Kendall Graveman and Sean Nolin.

July 28, 2015: Anthopoulos trades Reyes, Hoffman and pitchers Miguel Castro and Jesus Tinoco to the Colorado Rockies to acquire five-time All-Star shortstop Troy Tulowitzki and reliever LaTroy Hawkins.

July 30, 2015: The Blue Jays acquire ace David Price from the Detroit Tigers for a trio of left-handed pitching prospects; Daniel Norris, Matt Boyd and Jairo Labourt.

July 31, 2015: Anthopoulos acquires outfielder Ben Revere from the Philadelphia Phillies in exchange for pitchers Jimmy Cordero and Alberto Tirado.

September 26, 2015: The Blue Jays clinch a playoff spot for the first time since 1993.

Embedded ImageSeptember 30, 2015: The Blue Jays clinch the AL East with a 15-2 blowout win over the Baltimore Orioles.

October 14, 2015: The Blue Jays defeat the Texas Rangers in Game 5 of the American League Divisional Series to advance to the American League Championship Series.

October 23, 2015: The Blue Jays lose 4-3 to the Kansas City Royals in Game 6 of the ALCS, eliminating them from the playoffs.