When Alex Anthopoulos pulled the trigger on a massive 12-player deal with the Miami Marlins, he made one of the biggest deals - in terms of number of players - in major league history.
In terms of Blue Jays history, it's a trade that is right near the top of the list when it comes to changing the identity of the team.
The most memorable and impactful deal in franchise history happened on December 5, 1990 when the club dealt fan favourites Tony Fernandez and Fred McGriff to the San Diego Padres for Roberto Alomar and Joe Carter. Fernandez was a three-time All-Star who had spent most of the previous decade playing Gold Glove defence at shortstop with a strong batting average, while the power-hitting McGriff slugged 105 home runs over the previous three seasons.
It was a lot to give up, but general manager Pat Gillick had a pretty good idea of what he was getting back. Alomar, just 22, had already made an All-Star appearance and was a star in the making as a five-tool player with a ton of talent. Carter was already an established run producer, having averaged over 100 runs batted in per year over the previous five seasons, mostly with the Cleveland Indians.
Together of course, Alomar and Carter would become key elements to the Blue Jays' two World Series titles in 1992-93.
In fact, some of the biggest names the Blue Jays ever acquired were brought in as support during the championship era. In 1992, Toronto traded prospect Jeff Kent for former Cy Young winner David Cone. In 1993, Rickey Henderson was acquired at the trade deadline for pitcher Steve Karsay.
Pitcher David Wells was part of two of the Jays' more significant pitching deals. The New York Yankees traded him to Toronto along with Homer Bush and Graeme Lloyd in exchange for Roger Clemens on Feb. 18, 1999.
Just over two years later, Wells was dealt away in what is considered by most as one of Toronto's worst deals. The lefty was sent to the Chicago White Sox as part of a six-player deal that brought back another lefty, Mike Sirotka. Unfortunately for the Blue Jays, Sirotka arrived as damaged goods with significant shoulder injuries that prevented him from ever pitching in Toronto. A 15-game winner in 2000, Sirotka never pitched in the majors again.
The Blue Jays have made other significant deals. On Nov. 8, 1999, the team shipped popular outfielder Shawn Green to the Los Angeles Dodgers for Raul Mondesi and Pedro Borbon.
One of the biggest recent deals that the Blue Jays made happened when they traded ace Roy Halladay to the Philadelphia Phillies. On Dec. 16, 2009, Toronto dealt the righty along with cash in exchange for Kyle Drabek, Travis d'Arnaud, and Michael Taylor. Drabek has shown promise in limited appearances for the Blue Jays but is now coming back from Tommy John surgery. d'Arnaud is often considered the Jays' catcher of the future.
On Jan. 21, 2011, the Blue Jays sent star centre fielder Vernon Wells to the Los Angeles Angels for Mike Napoli and Juan Rivera. The move was largely seen as a way to save salary for the Jays, who had signed Wells to a back-loaded, seven-year, $126 million contract after the 2006 season. Wells was still owed over $80 million when he was dealt to the Angels.