Over the years, every General Manager is judged on both the deals they made and the ones they didn’t. Whether it is a missed draft choice, a bad trade, or one they never made at all, their legacy is defined by both the actions they made and the possibilities they missed. The Toronto Blue Jays have had their fair share of missed opportunities over the years. Every missed opportunity brings up the question of what might have been if the Jays had made the deal available and how might it have changed their future?
1993 – Randy Johnson for Mike Timlin and Steve Karsay
Midway through the Jays’ 1993 championship season, GM Pat Gillick was hunting for additional support at the trade deadline. At the time, he was shopping former first round pick pitcher Steve Karsay for a marquee player. By the end of July, he’d narrowed it down to two potential trades; Rickey Henderson from the Oakland Athletics and Randy Johnson from the Seattle Mariners.
Both choices had their advantages; Henderson was cheaper and the premiere leadoff hitter on the market. Johnson was a hard throwing lefty who had led the AL in walks for three years in a row but was also a dominant strikeout pitcher and in the middle of a career year. In addition, Henderson would be a true rental; a free agent at the end of the year while Johnson was under control until 1998.
Gillick settled on the Johnson trade and contacted Seattle GM Woody Woodward to make the trade. Unfortunately, Woodward was allegedly out golfing at the time and couldn’t be reached. Gillick contacted Oakland GM Sandy Alderson regarding a deal for Henderson. Alderson agreed to the deal and they finalized sending Steve Karsay and a player to be named later. Woodward contacted Gillick back later to agree to the deal to send Johnson to Toronto for Karsay and reliever Mike Timlin. Gillick felt that since he’d given his word, he couldn’t back out on the deal with Alderson and made the trade for Henderson.
While It is hard to criticize a deal that helped the Jays win their second championship title, the idea of Johnson in the Jays rotation until 1998 makes you wonder if it might have extended their competitive window. Imagine a 1997 rotation that included Hentgen, Johnson, Williams and Clemens.
OOTP What If: The Jays would win the 1993 Championship Season 4-1 over the Atlanta Braves. When the strike began in 1994, the Jays were 9 games ahead in the division before the season ended. They’d come back to win the World Series in 1995. However, after dismal starts in 1996 and 1997, the Jays would finish no higher than third, watching the Expos become the second non-American team to win the World Series in 1997.
2002 – Jose Cruz Jr for David Wright
JP Ricciardi still is a favourite punching bag in Toronto, maligned for a host of reasons, both real and imagined. One criticism that is true is that Ricciardi and his Front Office missed spectacularly on a number of franchise changing opportunities during his tenure. The first was in 2002, when a third place Jays team was offered a trade for OF Jose Cruz Jr. Cruz was an inconsistent player, considered to have star potential, especially after his dominant offensive year in 2001. However, he was a poor fielder, in the midst of an average year, and his contract was up at the end of the season.
Mets GM Steve Phillips saw Cruz as a key upgrade to his line for his contending team and approached Ricciardi about a deal centered around prospect David Wright, their second selection in the 2001 draft. Ricciardi, seeing Cruz as a major league asset, refused to deal him for a prospect so low down in the Mets system. His decision became even more questionable when at the end of the year, he declined to offer arbitration, the version of a qualifying offer at the time, which allowed Cruz to leave via free agency for nothing. This would be repeated soon after with Carlos Delgado.
Wright turned into ‘Mr Met’, a perennial All-Star who would rack up close to 50 bWAR over 11 seasons at 3B before being sidelined by injuries. Replacing Cory Koskie as the Jays 3B in 2004 at minimal cost, the Jays would have had significantly more financial flexibility as well as an improvement by multiple wins especially during the 2006-2007 when the Jays were closer to a potential upset.
OOTP What If: While Wright’s rookie season and several subsequent years wouldn’t move the dial much, in 2007, the Jays snuck into the Wild Card game, squeaking in ahead of Boston and sweeping the Yankees before losing the World Series ironically to the Mets. However, following a massive off-season ahead of the 2013 season, Wright would come close to winning the Triple Crown as the Jays dominated the league and won the World Series 4-1 against the San Francisco Giants
2005 – Ted Lilly for Ryan Howard
In 2005, the Jays were viewed as a team edging towards contention. They had a solid line-up of solid performers like Vernon Wells, Frank Catalanotto, and Gregg Zaun and emerging potential stars like Orlando Hudson, Alex Rios, and Aaron Hill. Their rotation had over-performed behind Roy Halladay, with strong seasons from Gustavo Chacin, Ted Lilly and Josh Towers and their bullpen was solid. The Phillies approached GM Ricciardi with a deal to help improve their rotation which was considered a weak element compared to their dynamic lineup. The Phillies offered Ryan Howard, an exceptional prospect who was dominating in the minor leagues. However, the Jays were rotating Shea Hillenbrand and Eric Hinske through 1B and DH with Aaron Hill, which they saw as a potential alignment for the future.
Lilly would depart the Jays following the 2006 season. Howard would win Rookie of the Year in 2005 and MVP in 2006. Neither Hinske or Hillenbrand would emerge as the answer at first, while Hill would move to second following the Hudson trade. While Howard is best remembered for the collapse of offensive value following the bulk of his huge contract, Howard was worth over 20 bWAR during his first six years of control in the majors.
OOTP What If: While missing Howard was a massive loss for Ricciardi, multiple scenarios failed to produce a result that allowed the Jays to find a way back to the post-season, even as they improved. In 2006, the Jays would miss the Wild Card spot by 2 games and in 2010 by 3 games, with their most successful seasons with Howard on the team.
2007 – Alex Rios for Tim Lincecum/Matt Cain
By 2007, the Jays were deeply mired into year after year of third place finishes, with either excellent teams undone by injury or key bouts of inconsistency and under-performance that cost them just enough to sink them in the ultra-competitive AL East. Coming off of a solid season, GM Ricciardi was casting about for ways to close the distance between his club and the behemoths of the East. Alex Rios looked like he was emerging as a star right fielder, with a combination of power and speed, despite the odd mental lapse in the field. The San Francisco Giants were in the position of trying to replace the generational talent of Barry Bonds and had approached Ricciardi about a potential trade.
The two potential pieces that Rios was considered worth were young pitchers Tim Lincecum and Matt Cain. Both were highly regarded young arms, but the Giants were prioritizing offense at the time. While the Jays felt they had a top one-two of Halladay and Burnett in their rotation, the pieces behind them were promising but inconsistent, unproven or injury prone. Unfortunately for the Jays, Ricciardi believed that his rotation was more advanced than his offense and that subtracting Rios would hurt more than adding either of the pitchers. Rios continued up and down years, never reaching his perceived potential, eventually being picked up with his sizable contract off waivers for nothing in return. Lincecum especially would blossom, turning in over 20 bWAR over the next four years. Meanwhile, after the 2008 season, the Jays rotation would fall apart as opt-outs, injuries and underperformance sank the team and eventually cost them their ace, Roy Halladay
OOTP What If: In 2008, the Jays finished five games over .500 and still finished 4th. Running seasons with the Tim Lincecum trade turns the Jays into a juggernaut, winning the AL East in 2008 and the Wild Card in 2009 and 2010. Although they’d only make the World Series in 2008 (and win in shutdown fashion), a mix of health and three bonafided aces at the top of the rotation (Burnett did not use his opt-out) showed the Jays as a series contender in the division.
2009 – Roy Halladay for Jared Weaver/Joe Saunders, and Peter Bourjos
In early 2009, Roy Halladay made it clear to then GM JP Ricciardi that he was not open to a contract extension following the 2010 season which was the final year on his existing contract. Ricciardi opened up initial trade discussions with a number of clubs, guided by Halladay’s desire to join a contending club. The Anaheim Angels made an aggressive offer leading up to the trade deadline, offering either Jared Weaver or Joe Saunders, two young starters and defensive wizard in center field, Peter Bourjos. Ricciardi had his eye on young infielder Erick Aybar, who was having an excellent year at the plate to go along with his excellent defensive role at second and short. Eventually, talks broke down over Aybar, as the Angels decided it was an ask too far, especially since Halladay would not guarantee a contract extension during the season.
Sadly for the Jays, Jared Weaver was on the cusp of a breakout that would make him one of the best starters in baseball. Although Bourjos never truly broke out to meet his potential, he posted 7 bWAR between 2010 and 2011 with plus defense. The deal with the Phillies, made by Anthopoulos following Ricciardi’s dismissal as GM, netted three highly regarded prospect, but the only real value through a series of trades would eventually be Devon Travis. Meanwhile, in 2011, Weaver and Halladay would face off against each other as the opposing starting pitchers at the All-Star Game.
OOTP What If: Much like the Ryan Howard trade, while the Jays posted a slightly better record following the trade, it didn’t close the distance between the team and a playoff berth for the first few years. Weaver’s genius on the mound couldn’t compensate for the turnover in talent. However, following the trade for the 2013 season with the Marlins, the Jays went on to win a franchise record of 108 games and take the World Series from the Los Angeles Dodgers.
2018 – John Donaldson for Jack Flaherty
One of the most painful recent misses was the possible trade of Josh Donaldson to the St. Louis Cardinals before the 2018 season. The Jays had come off of their first two playoff appearances in over two decades in 2015 and 2016. While they had faltered due to injury in 2017, there was still a sense that the Jays still had a competitive window open to them, with the Yankees banking on young talent, the Orioles suffering significant departures, and the Red Sox the main competition to beat. The key component would need to be the dominant offensive production of Donaldson in the lineup. The Cardinals offered promising young starter Jack Flaherty and at least one other unnamed piece for Donaldson. However, with the half-in, half-out strategy of the Jays front office, they felt that even if they didn’t compete, they’d still be able to move Donaldson for a significant haul at the trade deadline.
This didn’t work. At all. In the slightest.
Donaldson would be injured most of the year and end up getting flipped at the last moment for Julian Merryweather of the Cleveland Indians. Flaherty would have a solid year in the Cardinals rotation in 2018 and break out in 2019, posting almost 6 bWAR. Unless Merryweather breaks out as an ace starter, it is clear that missing Flaherty has hindered the Jays rebuild and return to competitiveness.
OOTP What If: The Jays clearly have been more than one starter away from competing. Adding Flaherty to the team didn’t change 2018 at all, but in 2019, the Jays finished a game above .500. However, running 2020-2023, the combination of Pearson, Flaherty, and surprisingly Thornton turn the Jays into a legitimate contender and 90+ game winning team year after year.