5 of the worst trade deadline deals in Blue Jays history

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.