Blue Jays: 3 trades the franchise wishes they could have back

In 1990, Blue Jays General Manager Pat Gillick had a decision to make. He had to find room in the lineup for up-and-coming first baseman John Olerud and get his club, which had fallen to second place after advancing to the ALCS the previous year, over the imaginary hump.

Gillick swung a deal that changed the fortunes of the franchise. He dealt franchise icon Tony Fernández and Fred McGriff to the San Diego Padres for Joe Carter and Roberto Alomar. It was a big risk, but it worked out as the Blue Jays, with Carter and Alomar, went on to win consecutive World Series titles.

That trade worked out for the Blue Jays. But for every trade that turns out well, there is another that can come to haunt the club.

The Blue Jays have been on the wrong end of some deals that set the club back years. Future Hall of Famers and All-Stars headed out of Toronto, with little coming back in return.

Three trades, in particular, proved disastrous for the Blue Jays. Here are the three moves the club wishes they could do over again.

More Articles About Blue Jays Trade History:

No. 2 Saying goodbye to a franchise icon

For 12 years, Roy Halladay gave the Blue Jays everything they could’ve asked for.

He won 20 games twice. He won the Cy Young Award in 2003 and finished in the top-five four other times. By the end of 2009, he trailed only Dave Stieb in a number of franchise records: wins, ERA, strikeouts, shutouts, and WAR. He was the consummate workhorse, leading the league in complete games five times in a span of seven seasons.

But he had yet to accomplish one thing: pitch in the postseason. The Blue Jays constantly played in the shadow of the Yankees and Red Sox in the AL East. They won between 80 and 87 games seven times during the decade but never seriously contended for a playoff spot.

Halladay, with a year left on his contract, saw his time running out. After the 2009 season, when he won 17 games and finished third in the AL with a 2.79 ERA, he requested a meeting with new General Manager Alex Anthopoulos (who had only been on the job for a few months) and team president Paul Beeston.

“Look, if you guys are rebuilding, my clock is getting short. I don’t know how long I have and I don’t want to go through another rebuilding process. I would love nothing more than to win a World Series championship in Toronto, but I don’t know that I have that time,” Halladay said, as recounted by MLB.com’s Todd Zolecki in Doc, his 2020 biography of Halladay.

Halladay requested a trade. Anthopoulos connected with Phillies General Manager Ruben Amaro Jr. and, after much back-and-forth bargaining, the two sides agreed on a package: Halladay was sent to Philadelphia in exchange for Kyle Drabek, Travis d’Arnaud, and Michael Taylor.

Halladay further cemented his Hall of Fame status with the Phillies, winning yet another Cy Young Award, pitching a perfect game, and throwing only the second postseason no-hitter in history. The Blue Jays hoped Drabek, the son of 1990 Cy Young winner Doug Drabek, would step out of Halladay’s loft shadow. He never did.

Drabek was the 25th-ranked prospect in the league by Baseball America. He was the top pitcher in the Phillies system and was described as having the best curveball in the organization to go along with a low-90s fastball. He had a 3.19 ERA in 23 starts in the minors in 2009, striking out 8.5 batters per nine innings.

Drabek made his MLB debut in September 2010 and made 14 starts for the Blue Jays in 2011. His ERA ballooned to 6.06 and he was demoted to the minors in June before earning another September callup. In June 2012, while pitching against the Washington Nationals, Drabek felt a pop in his elbow and required Tommy John surgery. He appeared in just five more games with the Blue Jays, finishing his career in Toronto with an 8-15 record and a 5.27 ERA.

The other pieces in the trade never played for the Blue Jays. d’Arnaud was part of the 2013 deal with the Mets for R.A. Dickey and has gone on to have a 10-year career in the Majors, including winning a World Series with the Braves—where he was reunited with Anthopoulos—in 2021. Taylor was traded to the Athletics for Brett Wallace the same day as the Halladay trade; Wallace, in turn, was traded to the Astros for Anthony Gose.

Halladay is forever memorialized with his No. 32 banner hanging from the rafters at the Rogers Centre. He’s the only player to have his number retired by the Blue Jays and was the first player elected to the Hall of Fame who began his career in Toronto (Fred McGriff became the second this year). He gave the Blue Jays everything he had, even if he had to go elsewhere to fulfill his postseason dreams.

No. 1 The Mike Sirotka debacle

David Wells has called the 1999 trade that sent him back to the Blue Jays the worst day of his career. His exit from Toronto may have been one of the worst days for the franchise.

Wells, the husky left-hander with the rubber arm and devastating curveball, debuted with the Blue Jays in 1987 and was a member of the 1992 World Series champions, pitching four games out of the bullpen without allowing a run as the Blue Jays defeated the Atlanta Braves.

He arrived for a second stint with the Blue Jays in 1999, part of a trade that sent reigning Cy Young Award winner Roger Clemens to the Yankees, with another World Series ring and a perfect game on his resume. But he wasn’t happy. Wells loved being a Yankee. He loved the allure of wearing the iconic pinstripes. He idolized Babe Ruth, rubbing Ruth’s plaque in Monument Park before every start. He even wore Ruth’s cap during one game.

Wells gave the Blue Jays 37 wins over the next two years. He led the American League in complete games both years and started the All-Star Game in 2000, when he won 20 games for the only time in his career. But he wanted out, and Blue Jays General Manager Gord Ash obliged him.

Ash received two offers, from the New York Mets and the Chicago White Sox. The Mets offered left-hander Glendon Rusch and prospect Grant Roberts. But Ash decided to take the White Sox offer of pitchers Mike Sirotka and Kevin Beirne, outfielder Brian Simmons, and prospect Mike Williams.

The centrepiece of the deal was Sirotka. The left-hander was coming off his best season at the age of 29, winning 15 games for the White Sox in 2000 with a 3.79 ERA. He was about to join a Blue Jays rotation that already included rising stars Chris Carpenter and Roy Halladay.

His physical with the Blue Jays went well. Then a follow-up visit with renowned Dr. James Andrews revealed the bad news: Sirotka had a partial tear of the rotator cuff in his left shoulder and a torn labrum. The Blue Jays sought compensation from the White Sox for failing to disclose Sirotka’s health status. They appealed to the league office. Finally, Commissioner Bud Selig delivered a scathing 14-page ruling against the Blue Jays.

“After careful consideration of all the information before me, I uphold the transaction and deny the Toronto club’s claim for relief,” Selig wrote. “Although there is a dispute about whether certain facts about Sirotka’s condition were disclosed before the clubs agreed to the trade, the Toronto club talked directly to Sirotka about his health on the day of the trade and believed it had the opportunity to make the trade conditional. The Blue Jays never elected to do so.”

Sirotka never left the dugout with the Blue Jays. He never appeared in another Major League game. Beirne appeared in just five games with the Blue Jays; Simmons played 60 in 2001, his last year in the Majors. Williams never made it to the big leagues.

Wells, meanwhile, after a year with the White Sox, got his wish: he returned to the Yankees in 2002.