The Blue Jays weren't necessarily expecting big things from Bautista at the time, but they needed him as a temporary midseason replacement for the injured Scott Rolen. They only had to part with a fringe catching prospect to get the deal done, and his versatility at first base, right field and second base kept Bautista on the team even after Rolen returned.
Two years later, Bautista made franchise history by hitting 54 home runs in a single season. He has been one of the elite power hitters in the game since, and this trade likely goes down as the most lopsided trade the Blue Jays have made regardless of the time of year.
2. Sept. 22, 1987: Blue Jays acquire right-handed pitcher Juan Guzman from the Dodgers for second baseman Mike Sharperson.
Blue Jays general manager Pat Gillick thought he was making a deal for Jose Offerman but instead got stuck with Guzman at the last minute. That turned out to be great news for the Blue Jays as Guzman went a combined 40-11 with a 3.28 ERA in his first three seasons in Toronto.
All three of those years included a spot in the postseason and Guzman became a dominating presence during Toronto's glory years. Guzman also won the American League ERA crown in 1996 while Sharperson only received regular playing time for three years of his career.
3. Aug. 27, 1992: Blue Jays acquire pitcher David Cone for second baseman Jeff Kent and outfielder Ryan Thompson.
This is one of those rare trades that worked out for both teams. Cone went 4-3 with a 2.55 ERA down the stretch to help lead the Blue Jays into the postseason. Once there, he played a pivotal role in helping the club capture its first of two World Series championships.
Cone departed at the end of the season, but it's debatable whether Toronto would have won it all if Gillick hadn't pulled the trigger on this deal. The cost was high as Kent went on to have an outstanding career, but with Roberto Alomar firmly entrenched at second base, it made perfect sense for both sides to part ways.
4. July 31, 2009: Blue Jays acquire third baseman Edwin Encarnacion, right-handed pitcher Zach Stewart and right-handed pitcher Josh Roenicke from the Reds for Rolen.
The Blue Jays' primary targets were Stewart and Roenicke, but the only way Cincinnati would agree to the trade was if Toronto would also take Encarnacion. That was the deal breaker, because of Encarnacion's salary and the fact the Reds needed to create a starting spot at third for Rolen.
It took Encarnacion a couple of years to put everything together, but by 2012, he was one of the best power hitters in the game. He hit 42 homers and drove in 110 runs while following it up the next year with an All-Star campaign.
5. July 31, 1997: Blue Jays acquire outfielder Jose Cruz Jr. from the Mariners for right-handed pitcher Mike Timlin and left-handed pitcher Paul Spoljaric.
The Blue Jays sold high on a pair of relievers to acquire one of the best young outfielders in the game at the time of the deal. Cruz burst onto the scene earlier that season by hitting 12 homers in just 49 games for the Mariners and proceeded to hit an additional 14 in his next 55 with Toronto.
The production didn't quite meet the hype later on in his career, but Cruz still managed to enjoy six successful seasons in Toronto. The highlight came in 2001, when he hit 34 homers while also stealing 34 bases.