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.

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No. 3 A future All-Star taunts the Blue Jays

The summer of 2000 was a good time for the Toronto Blue Jays. They were contending for the AL East lead. The formidable Yankees suddenly seemed vulnerable. The Blue Jays were just 1.5 games out in the division. Carlos Delgado was having an MVP-caliber season.

But the pitching staff needed help. Roy Halladay’s once-promising career derailed as he posted a 10.64 ERA and was sent down to Single-A. Chris Carpenter was demoted to the bullpen. To solve the problem, GM Gord Ash went shopping and settled on Esteban Loaiza, a 28-year-old right-hander who was 5-6 with a 5.37 ERA in 17 starts for the Texas Rangers.

The Blue Jays gave up two prospects for Loaiza, Michael Young and Darwin Cubillan. Young, a fifth-round pick out of UC-Santa Barbara in 1997, was batting .275 with six homers at Double-A at the time of the trade. Cubillan, a right-handed pitcher, had made his MLB debut back in May and had an 8.04 ERA in seven appearances. It seemed like a small price to pay for immediate help. They were wrong.

Loaiza went 5-7 with a 3.62 ERA in 14 starts for the Blue Jays the rest of the season, but the team’s fortunes didn’t improve. They went just 32-34 after the trade and finished in third place in the division, 4.5 games back of the Yankees. They wouldn’t come any closer to the playoffs for another 15 years.

Loaiza won 25 games over the next two seasons with the Blue Jays, posting a 4.96 ERA in 69 starts before he signed with the White Sox as a free agent. It was there that he had his best season, finishing runner-up for the AL Cy Young Award in 2003.

As for Young, he spent the next decade showing his former team what they had given up. Young starred for the Rangers for 13 years. He made seven All-Star teams. He won a batting title. He twice drove in at least 100 runs in a season.

The Rangers made the World Series in back-to-back years with Young in their lineup. He left the club after 2012 as the franchise’s all-time leader in games played and hits. Only Juan González and Rafael Palmeiro, two players with Hall of Fame credentials if not for their ties to performance-enhancing drugs, drove in more runs in a Rangers uniform.

Loaiza never became the star the Blue Jays envisioned when they made the trade. Young did, a constant reminder of what the Blue Jays could’ve had.

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.