The Toronto Blue Jays’ Best Trade Deadline Trades of All-Time


The Toronto Blue Jays have had a history of impactful trades throughout the franchise’s 37 years of existence.

Whether the Blue Jays were acquiring a player to help put them get over the top during their glory days, or trading away a promising prospect for an average pitcher like Esteban Loaiza, the Blue Jays have done it all at the trade deadline.

While not all the trades have worked out in favour of the Blue Jays, let’s be honest: no team has had every trade work out for them.

With the trade deadline set to take place tomorrow, let’s take a look back at the Blue Jays’ best trade deadline acquisitions over the years. While not every trade was a home run, these trades in particular helped the Blue Jays franchise in an impactful way.

5. July 31, 1997: Toronto Blue Jays acquire outfielder Jose Cruz Jr. from the Seattle Mariners for pitchers Mike Timlin and Paul Spoljaric

During the 1997 season, general manger Gord Ash sold a pair of established deliverers for young, up-and-coming outfielder Jose Cruz Jr.

Cruz would belt 14 home runs and steal 14 bases in his first 55 games with the Blue Jays. Although Cruz would never live up to the hype, he showed flashes of excellence during the 2000 and 2001 seasons, where he would record his only 30/30 season.

After the Blue Jays in 2003 via free agency, Cruz Jr. would go on to play for seven different teams to round out his career, never regaining his 30/30 form.

4. July 31st, 1993: Toronto Blue Jays acquire outfielder Rickey Henderson for pitcher Steve Karsay and outfielder Jose Herrera

March 31, 2014; Oakland, CA, USA; Oakland Athletics former player Rickey Henderson after throwing out the ceremonial first pitch before an opening day baseball game against the Cleveland Indians at Coliseum. The Indians defeated the Athletics 2-0. Mandatory Credit: Kyle Terada-USA TODAY Sports

Blue Jays general manager Pat Gillick acquired speedster Rickey Henderson from the Oakland Athletics in 1993 to help push the team to their second straight World Series title.

Henderson brought a gaudy resume with him to Toronto, as he was a 10-time all-star, AL MVP and ALCS MVP before joining the Blue Jays in 1993. Although most of Henderson’s accolades were collected on other teams, he was a part of one of the most historic plays in Blue Jays history – the “touch-em-all” Joe Carter home run.

While Henderson never posted the statistics with the Blue Jays like he did for other teams, he did post a .356 on base percentage, as well as great defence.

3. July 31, 2009: Toronto Blue Jays acquire third basemen Edwin Encarnacion, pitchers Zach Stewart and Josh Roenicke from the Cincinnati Reds for third basemen Scott Rolen

May 18, 2014; Arlington, TX, USA; Toronto Blue Jays designated hitter Edwin Encarnacion (10) bats during the game against the Texas Rangers at Globe Life Park in Arlington. Mandatory Credit: Kevin Jairaj-USA TODAY Sports

When this trade first happened, the Blue Jays looked to be coming out on the short-end of this deal. Pitcher Josh Roenicke was a train wreck in Toronto posting a 6.38 ERA and allowing 26 earned runs in 36.2 innings pitched. Zach Stewart lasted all of three starts, and third basemen Edwin Encarnacion was struggling mightily at the plate, leading to a demotion to AAA Las Vegas.

Fast-forward to now and this deal looks like a steal for the Blue Jays.

Edwin Encarnacion has blossomed into one of the league’s most fearsome hitters, amassing 121 home runs and 339 RBIs since 2011. During that time, Encarnacion has easily cemented himself as one of the Blue Jays’ cornerstone players heading into the future.

2. August 27, 1992: Toronto Blue Jays acquire pitcher David Cone from the New York Mets for second basemen Jeff Kent and outfielder Ryan Thompson

Blue Jays general manager Pat Gillick made an aggressive move by acquiring starting pitcher David Cone for highly touted second base prospect Jeff Kent.

While Cone turned out to be merely a rental player, he did help the Blue Jays clinch a post-season birth, and would help anchor their rotation en route to the franchise’s first World Series championship.

Cone would leave the Blue Jays at the end of the season, but his impact on the Toronto Blue Jays was undeniable. Without Gillick making the deal for Cone, it’s debatable whether the Blue Jays would have won their first World Series.

Although Jeff Kent would turn out to be a phenomenal player, Roberto Alomar was entrenched at second base for the Blue Jays, so the deal for Cone made sense.

1. August 21, 2008: Toronto Blue Jays acquire third basemen/outfielder Jose Bautista from the Pittsburgh Pirates for catcher Robinson Diaz

Jul 11, 2014; St. Petersburg, FL, USA; Toronto Blue Jays right fielder Jose Bautista (19) at bat against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

While the Blue Jays didn’t expect much more than a temporary replacement for the injured Scott Rolen when they initially made this trade, they got significantly more than just a depth player. To be honest, the Blue Jays could have never dreamed of the return Bautista has delivered.

Parting with a mid-level prospect like Robinson Diaz was an absolute bargain when you look back at this trade, especially since Diaz only played 49 games for the Pirates and Bautista has evolved into one of the league’s best sluggers.

On top of becoming an elite slugger, here are some of the accolades the man now known as “Joey Bats” has won with the Blue Jays: Silver Slugger Award, Hank Aaron Award, two-time AL all-star, two-time home run derby candidate, two-time 40 home run hitter, and the leader of the Toronto Blue Jays’ clubhouse.

I think it’s safe to say Jose Bautista is not only one of the biggest trade steals in Blue Jays history, but in MLB history as well.