The 8 Best And 7 Worst Moves By The Toronto Blue Jays Since Their Last World Series

O Canada, why did the Blue Jays go 22 years without a playoff berth?

After the 1993 World Series, what always happens in sports, regardless of the division, happened: the teams that were down on their luck became good again. Remember, the New York Yankees were likely headed for the American League pennant in 1994 before the strike and were in the World Series by 1996, while the Boston Red Sox were rebuilding and prepping for a late 1990s, early 2000s run. Baltimore still had Cal Ripken Jr. to lead the way and, by 1995, there were six divisions instead of four. A regression was bound to happen eventually, right?

So in the grand scheme of things, I don't think the Blue Jays going over 20 years without a playoff appearance was entirely on them making bad front office decisions. I mean, trading Michael Young for Esteban Loaiza isn't going to help your case, but it's also hard to compete with the Yankees and Red Sox offering insane contract after insane contract. Really, you have two options: try to build from the farm up, like the Tampa Bay Rays, or develop talent than trade them for unproven young talent or players that have fallen out of favor, like what the Baltimore Orioles did with some of their superstars.

Today, I'll do my best to look at what I believe to be some of the best and worst front office decisions by the Toronto Blue Jays since 1993. Any decisions that have been made in the past year, such as letting Edwin Encarnacion walk or signing Kendrys Morales, are not eligible. At the same time, off-the-field issues such as the team standing by a player are not eligible either.

Grab your passport, switch currencies, and prepare for some really nice people because we're headed to Canada.

17 Best: Bringing back Cito Gaston

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What? How could I put this on here? Look, I get that Toronto Blue Jays fans were and remain mixed about Cito Gaston's second stint with the Toronto Blue Jays from 2008-10, but I thought it was a smart move. When you're playing in a division where you know year after year who the two best teams are going to be, it's easy to lose confidence and play without much caring; go back and watch the Baltimore Orioles before Buck Showalter took over in 2010. They once gave up 30 runs in a game!

But, it is important to note there were some issues with Gaston's second tenure, including a reported mutiny in 2009 about his impatience with players, but maybe that was a good thing. In Gaston's final season, the Blue Jays improved by ten games and saw several key players for their future - Jose Bautista, especially - show flashes of brilliance. Small victories, friends. Gaston's return was a reminder to players that accepting third or fourth place in the A.L. East simply wasn't enough.

16 Worst: Trading Yan Gomes

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Let's put it this way: if Yan Gomes hadn't been below replacement value the past three seasons, he'd be much higher on this list. If Russell Martin was worth the massive contract he signed with the Blue Jays after the 2014 season, maybe Gomes wouldn't be on here. We're at a bit of a crossroads, so either we settle this through an old-fashioned duel or we revisit this trade. I like option two.

If the Blue Jays were trading Gomes for a decent level prospect or a Major League-level player that needed a change of scenery, this may not even make the list and we'd chalk it up to, "alright, no big deal." But to trade Gomes for a pitcher that had been worth -2.7 WAR in his first three full big-league seasons? What??? And to think this only the beginning...

15 Best: Taking the risk to re-sign Jose Bautista

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When Bautista needed a new contract going into the 2011 season, the Blue Jays took an absolute RISK by signing him to a five-year extension worth $64 million. Even if you make the argument that Bautista was going to get a raise regardless if he went from 50 home runs to 20 just off his versatility alone, to give the guy $64 million off one insane season is...well...insane!

And while we know how well it worked out for all parties, you have to really think about how dangerous this was. Remember, the Blue Jays had traded Vernon Wells around this time, so they knew what it was like to get burnt by a bloated extension...and they still gave Joey Bats the money!


13 Worst: The John Olerud Trade

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One of the rare players to jump directly to the majors after either high school or college, is it possible to forget John Olerud was a Toronto Blue Jay despite it being the team he spent the most time with - and the guy wasn't a journeyman, so it's not like we can pull the Richard Jefferson argument. Maybe the next time we have a player that spends close to or at least half of his career with a single team and we forget that, we can call it the John Olerud Effect.

Anyways, Olerud was a two-time World Champion with the Blue Jays and made the 1993 All-Star Game that year when he flirted with a .400 average and finished at .363, but was traded to the New York Mets in December 1996 for Robert Person. How'd the trade work out?

Olerud in three years with the Mets: 17.2 WARPerson in three years with the Blue Jays: -1.8 WAR


12 Best: Letting A.J. Burnett Walk

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Let's flash it back to 2008 for a second, where A.J. Burnett has just finished his second straight season where he's posted a 2.4 WAR and a 3.45 FIP (Fielding Independent Pitching) while helping the Toronto Blue Jays to a better-than-it-looks fourth place finish in the American League East. If you'll recall, Burnett was set to draw big bucks on the free agent market and at 32 years old on Opening Day 2009, would probably still have a few solid years left in the tank alongside Roy Halladay.

And while the Blue Jays did offer Burnett $54 million dollars over four years, they weren't willing to overpay when it became clear the former Florida Marlins star was down to the Boston Red Sox and New York Yankees. Given that the rotation was more or less Halladay and then everyone else, letting Burnett walk was a smart, underrated move that we'll applaud. At least the deal worked out for Burnett...

11 Worst: Letting Carlos Delgado Walk

Nick Turchiaro-USA TODAY Sports

And while it may have been smart to let Burnett walk in free agency, I don't know if I can say the same thing for Carlos Delgado after the 2004 season. Look, I get it: the guy was 32, had just hit .269, seen a major drop in production, drew major controversy for refusing to stand for God Bless America (make your Colin Kaepernick jokes in the comment section!), and had his lowest WAR (2.9) since a 3.6 mark in 1999. But Delgado was an absolute icon in Toronto and the Blue Jays let him walk...over financial concerns.

If Delgado looked absolutely lost at the plate in 2004, maybe this would be easier, but why would you let him go for "payroll constraints" when you knew what he was capable of? Again, a guy who wound up signing with the Marlins for $52 million over four years wasn't going to come cheap, but this was Carlos Delgado we were talking about! Luckily for both sides, things have been patched up and Delgado remains an icon in Toronto. Hooray!

10 Best: The Josh Donaldson Heist

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This is recent, so I don't think we need to rehash too much history here. After breaking out with the Oakland Athletics and nearly winning the 2013 American League MVP, Donaldson was traded to the Toronto Blue Jays in November 2014 for Brett Lawrie (huh???), Kendall Graveman (alright), Sean Nolin (huh?), and Franklin Barreto (wuh?) because the Athletics knew he'd soon demand a heavy payday. Never change, Oakland.

It didn't take long for Donaldson to prove his worth, winning the 2015 American League MVP and remaining one of the team's best hitters over the past three years. Donaldson may not be long for Toronto, especially if the Blue Jays consider a potential brief rebuild, but to look at what he's done and imagine what they had to give up speaks volumes to their front office.

9 Worst: Inter-division trades

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Look, I don't hate inter-division trades the way most people do, but I do think teams have to be careful when dealing big-name players to a team they play nearly 20 times a year - and potentially more in the postseason. The Yankees and Red Sox trading Kelly Johnson for Stephen Drew in 2014 isn't a problem, but the Blue Jays trading David Cone to the Yankees in 1995 for Jason Jarvis, Mike Gordon, and Marty Janzen?

Yeah, that's not good, especially when you remember Cone helped them to four World Series rings in five years and threw a perfect game in 1995. Four years later, the two would reconvene on a trade when the Jays sent Roger Clemens to the Bronx for David Wells, Homer Bush, and Greame Lloyd; and while Wells worked out in his two years with the Blue Jays, that was ALL the Jays could get for Clemens, the two-time reigning AL Cy Young?

I would've had to have thought Mike Lowell and Juan Rivera would be in that deal as well, but the trade definitely worked out for the Yankees. Toronto, on the other hand? Nope.

8 Best: Landing Jose Bautista for nothing

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Some will make the argument that this should be higher, but unlike Donaldson who was a proven star and would immediately start for the Blue Jays, Toronto acquired the journeyman Bautista in August 2008 for a player to be named later (catcher Robinzon Diaz) to serve a utility role down the stretch. If Toronto could somehow overtake the Yankees and Red Sox for the Wild Card, Bautista would be a valuable late-inning piece.

Absolutely no one saw Bautista's 50 home run season in 2010 coming, nor did anyone think he'd continue to hit home run after home run in the following seasons, so it'd be wrong to ignore landing them landing the future six-time All-Star for Robinzon Diaz of all people! But, because the leap to greatness was so unexpected, we can't put it much higher than fourth on the good part.

7 Worst: Overpaying B.J. Ryan

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Now granted, we're still in the era of overpaying closers, but this was something special. Out of nowhere, the Toronto Blue Jays signed former Baltimore Orioles closer B.J. Ryan to do the same for them; and on paper, this was a smart move as Ryan struck out 12.8 men per nine innings in 2005. Not bad! But to sign Ryan to a five-year, $47 million dollar contract?

Surprisingly, Ryan's first season with the Jays worked out, with him saving 38 games with a 1.37 ERA and 86 strikeouts in 72.1 innings. But, the money proved to be too much in the end as in four seasons with the Blue Jays, Ryan saved 118 games with a 160-69 K-BB ratio in 155.1 innings, though he missed nearly all of the 2007 season after Tommy John surgery. If Ryan was on a five-year, $20 million deal, maybe we'd look back differently?

6 Best: Offloading the Vernon Wells contract

Nick Turchiaro-USA TODAY Sports

I've said this before and I'll say it again: I do not think the Blue Jays signing Vernon Wells to a lucrative extension was a mistake, nor do I think he was the bust people make him out to be. Did Wells live up to expectations? Not necessarily, but what can you do? Most Blue Jays fans I've asked about Wells all seem to share pretty much the same answer: he wasn't the best, but he could've been a lot worse.

Don't you just love Canadian kindness?

In early 2011, the Blue Jays offloaded Wells to the Los Angeles Angels for Mike Napoli and Juan Rivera in a deal that nearly made this list for what happened after. This is a deal that can't be pinned on Tony Reagins, the unfortunately criticized ex-Angels general manager, but the Blue Jays getting rid of the bloated contract was smart? Then again, they'd be doing the opposite not even two years later....

5 Worst: Trading Michael Young

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Out of respect for tortured Blue Jays fans, I'll let FanSided's David Lynch cover this:

"The phrase “hindsight is 20/20” works all too well in the case of Michael Young. Toronto traded him before they really knew what they had. All they had in him was a future seven time All-Star, one time Gold Glover, and a two-time top-ten MVP finisher."

Putting Young so high may be unfair because the Blue Jays really didn't know what they had in him and it's another case of a prospect succeeding while a veteran failed, but come on. Michael Young is potentially going to have a Hall of Fame case when he's eligible in 2019 (I can't see him getting in before 2021 at the earliest right now) and the Blue Jays gave him up for nothing. For shame...


3 Best: Embracing being Canada's team..

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This is a weird one to put on the list, but given what I said in the intro and in the Cito Gaston entry, I think it's important to really commend the Blue Jays for embracing the need to be Canada's team. Remember, the Toronto Raptors had some really difficult years both before and after Chris Bosh left, while the Maple Leafs haven't done much of anything since 2004 (Auston Matthews is changing that!), so it was on the Blue Jays to step up.

And yes, this meant a little bit of tanking and a little bit of rebuilding the farm system, but you think about how competitive baseball really is beyond the parity and how few teams get to do that; if you're an awful team 162 games a year, you're losing profits on probably 75 of your 81 home games - and that's if you're lucky with a loyal fanbase. Some will call the recent influx of Blue Jays fans bandwagoners, but things could be worse. Toronto could have gone with the Cincinnati Reds approach...

2 Worst: Trading two top prospects for R.A. Dickey

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Before people ask why the blockbuster deal with the Miami Marlins isn't on here, at least there's a defense to be made there. If healthy, Josh Johnson was a Cy Young talent, Jose Reyes was still a solid shortstop and Mark Buerhle worked out as the Jays' ace; all the Blue Jays really 'lost' in the trade was Henderson Alvarez and Adeiny Hechavarria. Jake Marisnick, maybe, but that loss would be more on the Marlins who dealt him to Houston than the Blue Jays.

But trading Noah Syndergaard and Travis d'Arnaud for R.A. Dickey, even if he was coming off the 2012 National League Cy Young Award, makes no sense. At the time, Dickey was 38 years old, which is probably a bit too old to be trading two top prospects for. Mets fans may give Sandy Alderson a hard time, but this was an absolute steal.

Luckily for the Blue Jays, Dickey worked out and helped them to two playoff appearances, but imagine if the Blue Jays currently had a rotation of Marcus Stroman, Noah Syndergaard, Marco Estrada, and a healthy Aaron Sanchez? Woof.

1 Best: Giving Edwin Encarnacion one last chance

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Well, we were going to have to mention Encarnación at some point, but in this context? This move is easy to forget and I actually forgot about this until earlier this year, but the Toronto Blue Jays actually let Encarnación get claimed off waived by the Oakland Athletics...who then non-tendered him a month later! Two weeks later, the Blue Jays re-signed Encarnación, moved him to designated hitter after a slow start, and the rest is history.

You want to talk about risks? This may not be as big a risk as giving Bautista over 60 million after one fantastic season, but to give Encarnación one last chance to show he could be a big-league player? The irony is not lost that the Oakland Athletics had two chances at elite third baseman and let the Toronto Blue Jays have both...

Which of these deal is the best? Which is the worst? Make sure to let us know in the comment section below!

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