5 Worst Blue Jays Trades in Team History

The worst trades in Toronto Blue Jays history combine disappointing prospect packages and misjudged win-now moves. Some of these deals looked fine at the time and aged poorly, while others always looked like front-office mistakes. 

Bad trades have lengthened Blue Jays odds to win the division for years to come. Watching players succeed on another team is painful for fans, particularly if the player(s) they were dealt for don’t live up to expectations.

What Are the Worst Blue Jays Trades?

1. Esteban Loaiza for Michael Young and Dawrin Cubillan

Michael Young was hitting well in the lower levels of the minors when he was traded to the Texas Rangers with Darwin Cubillán in July 2000. Young went on to be selected for seven All-Star games and amass a 25.9 bWAR as a Ranger.

Esteban Loaiza had been a middling pitcher before arriving in Toronto. He posted a 95 ERA+ over two-and-a-half seasons as a Jay with a mediocre 1.45 WHIP.

2. Gabriel Moreno and Lourdes Gurriel Jr. for Daulton Varsho

None of these players were among the AL MVP favourites in baseball odds, but it still represents a major win for the Arizona Diamondbacks.

Daulton Varsho has a 91 OPS+ as a Blue Jay and woeful batted-ball metrics. The Diamondbacks sold high on him as a hitter. His defence is elite, but this was a high price to pay for a glove-first outfielder.

Lourdes Gurriel Jr. has hit 42 home runs and 57 doubles over two seasons in Arizona. Gabriel Moreno is a Gold Glove catcher with excellent plate discipline under team control for half a decade when this trade was made in December 2022. 

3. Roy Halladay for Travis d’Arnaud, Kyle Drabek, and Michael Taylor

It’s hard to get proper value when trading away a future Hall of Fame pitcher like Roy Halladay. 

The return of Travis d’Arnaud, Kyle Drabek, and Michael Taylor seemed fine when it was announced in December 2009. Drabek was an elite pitching prospect. Taylor was used immediately to acquire hitting prospect Brett Wallace, and d’Arnaud was on his way to becoming one of the best catching prospects in the sport.

Drabek, though, generated a -0.1 bWAR over 39 pitching appearances (30 starts) with an 81 ERA+. D’Arnaud was included in the disappointing R.A. Dickey trade three winters later, having not made the majors with the Jays. 

Wallace was traded for Anthony Gose before the 2010 trade deadline, and Gose was ultimately flipped for Devon Travis. 

4. Josh Donaldson for Julian Merryweather

Coming off a calf injury and only a couple of months away from free agency, the Jays would never get a haul for Josh Donaldson at the waiver trade deadline in 2018. 

The return of Julian Merryweather as a player to be named later from Cleveland was still very underwhelming, however. 

Donaldson only played 16 regular season games for Cleveland after the trade. However, he had a 127 OPS+ and 9.2 bWAR over the next three seasons, while Merryweather had a 75 ERA+ across 47 appearances as a Jay.

5. David Wells and Matt DeWitt for Mike Sirotka, Brian Simmons, Kevin Beirne, and Mike Wiliams

David Wells wasn’t happy in Toronto after the 2000 season, despite winning 20 games and finishing third in Cy Young voting. The Blue Jays decided to trade Wells and Matt DeWitt to the Chicago White Sox for a package built around Mike Sirotka.

Wells was heading into his age-38 season. DeWitt had an 84 ERA+ over 24 MLB appearances. 

This deal was still a terrible one for the Jays. 

Sirotka arrived with a fully torn labrum and a partially torn rotator cuff. He never pitched in the majors again after being traded to the Jays. Brian Simmons, Kevin Beirne, and Mike Williams combined for -0.7 bWAR as Blue Jays.