5 of the worst trade deadline deals in Blue Jays history

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.