5 of the worst trade deadline deals in Blue Jays history

When it comes to making deals at the MLB trade deadline, the key to success for any team is to make sure that the player(s) they receive in return end up being impactful for the organization. Whether it be for a contending team or a rebuilding team, "losing" a trade can have major impacts on the team for years to come.

For the Toronto Blue Jays, they have lost several trades at the deadline over the years, and some that they would clearly like a re-do on. As a result, we will take a look back at 5 of the worst trade deadline deals in Blue Jays history and, at the same time, sincerely hope that they won’t make a similar mistake this time around in 2025.

For the purpose of this piece, trade deals that were made within a couple of weeks prior to the trade deadline will still be considered a trade deadline deal.

5 of the worst trade deadline deals in Blue Jays history

2023 – Blue Jays acquired INF Paul DeJong and cash from the St. Louis Cardinals in exchange for P Matt Svanson

Compared to some of the big-name players that the Jays have moved or acquired at the trade deadline over the years, the one involving Paul DeJong might not be one of the most prominent ones made by Toronto. But it will forever be remembered due to the atrocity in his performance as a result of the acquisition.

When Bo Bichette was injured right before the eve of the trade deadline, the Jays scrambled to find his temporary replacement by trading for DeJong of the St. Louis Cardinals. In exchange they sent young pitching prospect Matt Svanson. However, the veteran infielder bombed out completely in his short tenure with Toronto.

In 13 games of action, DeJong recorded just three hits for a .068 average, .136 OPS, one RBI and a whopping 18 strikeouts in 44 total at-bats. With that, the Jays had no choice but to rush Bichette back from injury and ultimately designated DeJong for assignment just a little over two weeks after joining the club. By accumulating a -77 wRC+, he was hands-down one of the worst hitters the Jays had in franchise history. 

If that wasn’t bad enough, Matt Svanson has ascended from High-A to the majors in just a span of two years while evolving into a dominant reliever in the Cardinals organization. This season with St. Louis, he has posted a solid 3.12 ERA, 0.81 WHIP, along with 24 strikeouts in 26 innings pitched over 17 appearances and has become a trusted arm coming out of their bullpen. The Jays, who are currently pursuing bullpen help, could have used Svanson to solidify their relief corps.

2000 – Blue Jays acquired P Esteban Loaiza from the Texas Rangers in exchange for INF Michael Young and P Darwin Cubillan

The 2000 Blue Jays had a legitimate shot of making the playoffs for the first time since winning the World Series in 1993. They needed to add to their rotation and turned to the Texas Rangers as their trade partner, getting Esteban Loaiza in exchange for two young prospects.

It was a curious move at the time, since Loaiza was in the middle of a less-than-stellar season in which he compiled a 5.37 ERA and 1.53 WHIP in 20 games that included 17 starts with the Rangers. In the end, he would have a solid finish to his 2000 campaign with the Jays, posting a 5-7 record and a 3.62 ERA and 1.32 WHIP in 14 starts down the stretch.

However, Toronto would miss out on the playoffs in the end by 4 1/2 games. Loaiza would go on to have two more underwhelming seasons with the Jays before leaving via free agency following the 2002 season and becoming the ace for the Chicago White Sox the very next season.

As for the pieces going the other way, Cubillan didn’t materialize into much, but Young on the other hand would become a permanent fixture in the Rangers’ lineup while evolving into a legitimate MLB star for more than a decade.

Young was an All-Star seven times, along with capturing Gold Glove honours in 2008 and finishing in the top 10 in AL MVP voting twice. Eventually retiring with a career batting average of .300  and OPS of .787. The Blue Jays sure missed out on a potential franchise cornerstone with the puzzling deal.

2018 – Blue Jays acquired UTIL Brandon Drury and OF Billy McKinney from the New York Yankees in exchange for P J.A. Happ 

It was a rebuilding year for Toronto and at the 201 deadline they had a huge trade chip in J.A. Happ. With three consecutive seasons of double digits in wins between 2016-2018, including a 20-win season, Happ had become a proven winner.

The Blue Jays had the potential to help fast-track their rebuild by trading Happ, but they only managed to turn him into Brandon Drury and Billy McKinney in the trade with the Yankees. Happ would go on to shine for New York by going a perfect 7-0 with a 2.69 ERA and 1.05 WHIP down the stretch in 2018. Ultimately, he would help the Yankees reach the postseason for three consecutive years between 2018 to 2020.

As for the players that the Jays received, both Drury and McKinney would have underwhelming three-year tenures with the club, prolonging their rebuild as a result. Fortunately, the arrivals of Vladimir Guerrero Jr. and Bo Bichette would finally help turn the franchise’s fortunes around.

2003 – Blue Jays acquired OF Bobby Kielty from the Minnesota Twins in exchange for OF Shannon Stewart

The Blue Jays and the Twins both had records above .500, but weren't considered playoff contenders by the time the deadline rolled around. So it's strange the Blue Jays felt the need to deal away one of their longest-tenured players at the time in Shannon Stewart. In exchange, the Twins sent outfielder Bobby Kielty.

Stewart had been a mainstay in the Jays lineup for over a decade, posting a strong career .298 average, .805 OPS, with 595 runs scored, 222 doubles, 74 home runs, 370 RBIs and 166 stolen bases in 907 games with Toronto. 

By joining the Twins, Stewart provided that much-needed spark to the top of their lineup as he led Minnesota to a division title in three of the four seasons that he spent with the organization. More significantly, he managed to maintain his elite production more or less in line with his career numbers.

As for Kielty, he would last only the rest of the 2003 season with the Jays, amassing just a .233 average along with four home runs and 25 RBIs in 62 games. He would then be traded to the Oakland Athletics that very offseason for pitcher Ted Lilly, who would have three decent yet unspectacular run with Toronto between 2004 to 2006. It sure felt that the Jays failed to get full value from a stalwart like Stewart when all was said and done.

1995 – Blue Jays acquired P Marty Janzen, P Jason Jarvis, and P Mike Gordon from the New York Yankees in exchange for P David Cone

Many Jays fans might only remember David Cone in his first go-around with Toronto in helping the team capture their first ever World Series title in 1992 despite having to give up promising prospect Jeff Kent in the trade transaction in the process.

But Cone actually had a second stint with the Jays in 1995. Although Toronto fell out of contention early, the star right-hander still led the Jays pitching staff with a 9-6 record and a 3.38 ERA and 1.18 WHIP and became a hot commodity at the trade deadline.

In the end, Toronto would deal Cone to their rivals in the Yankees for three young pitching prospects in Marty Janzen, Jason Jarvis and Mike Gordon. Both Jarvis and Gordon never made it past Double-A as their MLB dreams ended before it even started.

As for Janzen, the main prize in the return, he did eventually make it to the big show with the Jays, but would only appear in 27 total games and compiling a dismal 6.39 ERA and 1.71 WHIP. He would then spend pretty much the rest of his professional baseball career in the minors and independent leagues.

As for Cone, in his six seasons with the Yankees, he posted a 20-win season in 1998, along with becoming an All-Star twice and finishing in the top 6 in AL Cy Young voting twice. More importantly, he would help the Jays arch rivals win the World Series FOUR times during those six years, making the trade one of the worst deadline deals ever made by Toronto.