Alex Anthopoulos’ Legacy: Is It What Jays Fans Think It Was?

By Mason McRae

One of the most talked about topics amongst Jays fans is the Ross Atkins vs Alex Anthopoulos debate. Some Jays fans absolutely refuse to give Atkins any sort of leeway, and love to point the finger at Shapiro and Atkins for the team’s current state, when in reality, the blame lies with the former GM – Alex Anthopoulos – and today you’ll fully understand how Alex Anthopoulos’ atrocious asset management is still affecting the Jays.

First things first, I want to make it clear that Alex Anthopoulos wasn’t a bad GM, nor a great one. He was just an average one, he had his flaws that balanced out his strengths. But in no way am I saying that he was/is one of the worst executives in the league. The meaning of this all is to educate the people thinking the Jays current state is because of mistakes created by the Atkins office.

When taking over the Jays on October 3rd, 2009. Anthopoulos wasn’t handed a very ideal situation, the Jays were an average team that needed to trade away their face of the franchise in Roy Halladay. Which led to AA’s first big mistake:  the Jays got Kyle Drabek, Michael Taylor, and Travis D’Arnaud for Halladay. Drabek was suppose to be Halladay’s heir apparent at the top of the rotation and never came close, while Taylor and D’Arnaud were shipped away. None of the 3 played a role for the Blue Jays, and the worst part – this wasn’t AA’s worst deal, it might’ve even been the third worst depending on who you ask.

Anthopoulos took a three-year break from blockbuster deals, and woke up in 2012 with a mission set in mind – “it’s now or never”.  He sent away a dozen highly touted prospects for a bunch of could-have-beens and veterans. The first atrocious 2012 deal was sending Yan Gomes and Mike Aviles ro Cleveland for Esmil Rogers. Yan Gomes became an average starting catcher for the Indians and would’ve saved the Blue Jays from the J.P Arencibia project that blew up in the Jays’ face, while Esmil Rogers was about as good as gone in his short tenure. 

The second of the hilariously bad 2012 deals, was signing Ceasar Izturis to a 3 year/11M deal. Izturis spent his entire time on the DL, or chewing gum on the bench. This takes us to the third mistake made in 2012. On November 19, 2012 the Blue Jays sent Justin Nicolino, Henderson Alvarez, Anthony DeSclafani, Yunel Escobar, Adeiny Hechavarria, Jake Marisnick and Jeff Mathis to the Miami Marlins for John Buck, Emilio Bonifacio, Mark Buehrle, Josh Johnson and Jose Reyes. The positive side of this trade: Mark Buehrle had a few decent seasons where he lead the league in run support and gave the Jays lots of innings when they needed them. The bad: Henderson Alvarez, Anthony DeSclafani, Adeiny Hechavarria, and Jake Marisnick became capable players on teams not based in Toronto. This one was bad, very bad, and it still somehow wasn’t his worst deal, maybe not even his second-worst deal.

Here comes the best of the worst, the infamous “Dickey for Syndergaard” deal. Luckily we got Josh Thole though, right? We also gave up on the last of the Halladay trade pieces in Travis D’Arnaud. It’s hilarious seeing people defend this trade on Twitter. Yeah, I’m serious – I still get people in my twitter mentions say crap like “Dickey ate innings for us and was always healthy, while Syndergaard keeps getting hurt”.  I’ve given up responding to those Tweets – I just assume it’s one of Anthopoulos’ burner accounts and move about my day.  Since I have to, here’s why the trade failed. Dickey’s best season (in Toronto) was worse than Syndergaard’s worst season in NY. Syndergaard would’ve been the clear cut ace for the Jays the last few seasons. If you’re one of the people defending this trade, do us a favour. Research the process of deactivating your twitter account.

Now, with the horrid 2012 over with, the road ahead looks bright.

It’s 2015, and Anthopoulos has turned around the entire Blue Jays organization, impressive – very impressive. They had one of the worst prospect pools when he took over and since then they’ve gathered a really bright young core that includes Aaron Sanchez, Roberto Osuna, Marcus Stroman and many more. This was Anthopoulos’ masterpiece in Toronto. I’ll give credit to him when it’s due, Anthopoulos is one of the best executives in the league when it comes to drafting and developing. 

At the 2015 deadline, the Jays acquire Troy Tulowitzki and LaTroy Hawkins for Jeff Hoffman, Jesus Tinoco, Miguel Castro and Jose Reyes. None of the Jays’ highly touted prospects worked out for Colorado, but neither did Troy Tulowitzki, who was great the 3 months they needed him in 2015 and after that, he became riddled with injuries that derailed his career. Side note: If Tulo wasn’t plagued with unbelievably bad luck with injuries, he would’ve been one of the best shortstops of our generation. Unfortunately though, he was just a massive waste of money for the three seasons they had him on the roster, until they dealt him to the Yankees and continued to cash his checks.

The last of the 2015 deadline deals, was the David Price deal. At the time, I loved it. We knew it was a rental and I was fine with it. Daniel Norris, Jairo Labourt, and Mat Boyd were the pieces going back, and at the time it looked like Norris would be the centerpiece. But now, Matt Boyd is by far and away the biggest part of the trade, Detroit got a great player in Boyd and still have him under control. This trade becomes a fail for Toronto because of losing in the ALCS and also losing valuable players after the 2015 season, while Price left for Boston.

That basically wraps up the recap of all of AA’s massive mistakes, now it’s time to put it all together.

The argument for the Anthopoulos truthers is: They won, now he’s gone and we aren’t. Basically, 21st century Jays fans haven’t experienced winning and would’ve given up anything for a taste of October baseball. I saw a great metaphor on twitter basically summing this article up on in one funny tweet. 



 He’s got a point, AA traded away their top prospects for a two year window at a championship and left the year before the ship sunk. The opposing argument is that he left a playoff team behind, the problem with that argument – is that Encarnacion left after a year and the Jays gained a first-round compensation that’s turned into their #1 pitching prospect in Nate Pearson (great asset management, point Atkins) and Bautista, Tulowitzki, Estrada, Martin and Donaldson were all becoming old and regressing (Maybe not Donaldson so much, that happened the following season). But the point is, Atkins was handed a system that had absolutely nothing aside from Vladimir Guerrero Jr, whom nobody knew about at the time because he was still so young and I believe Eric Pardinho was an AA signing, that was on the fringe of when AA left and Atkins joined the staff, so correct me if I’m wrong. But that’s all that was in the system, it was one of the worst in the league.

To conclude this all, AA was an adequate GM. He brought Toronto to the forefront of a championship and gave the Blue Jays fans two exciting seasons, but they didn’t win anything and threw away the future.

So thank you AA for a fun two years, but at what cost?

It’s time to rebuild, and in Atkins I trust!


6 thoughts on “Alex Anthopoulos’ Legacy: Is It What Jays Fans Think It Was?

  1. Any article that focuses on the strengths and weaknesses of the AA regime without talking about the Josh Donaldson trade (probably the best Blue Jay’s trade ever) or the Vernon Wells unloading is clearly a polemic. AA was too quick to unload rookies at the end of the steroid era when trading rookies for vets was becoming an increasingly bad idea. The Donaldson deal, along with his supposed involvement in getting Bautista, and being lucky to get EE back define that era. They also went all in to get Vlad. That being said I thought he overdid it on risky players and strict rentals when they went for it.
    I liked the new regime overall with my main criticism that they were too slow to unload aging assets getting very little for Bautista, EE, and Donaldson. They have now shifted to full rebuild and have drafted reasonably well, and although AA sold the farm he made some historic trades, and though Atkins rebuilt the farm he waited to long and got nothing for valuable assets.

    Liked by 1 person

  2. I can’t say I agree in the slightest with your assertion that AA was great at drafting and developing, at least not on the position player side of things. I struggle to name one really high impact player that was drafted by that regime in their entire time running the club, that’s downright embarrassing with the massive number of draft picks they gamed the system for early on. I will credit for the ingenuity that the regime displayed though.

    I also can’t really agree that the Marlins trade was really much of a failure, given that none of the players moved in the deal were ever anything more than average MLB players at their best. Henderson Alvarez had 2 decent seasons before health issues derailed him, Adeiny Hechavarria was never able to hit, Jake Marisnick is a career backup outfielder, Jeff Mathis is a career backup catcher, and Anthony DeSclafani has had one complete productive season. These guys don’t exactly make up a championship caliber core to say the least.


  3. You have AA exactly backwards. He was great at trades and terrible at drafting.

    The Halladay trade was not a bad trade. True, Halladay was an absolute ace, but he was under contract for just one more year and not only publicly declared his desire to leave a clear rebuild situation, but was willing to use his no-trade clause to pretty much dictate his destination. This was not a good bargaining position, and yet AA managed to pry 3 top 100 prospects as a return. Two of those guys had their careers derailed by injury (is that AA’s fault?) and the other was turned into Devon Travis. This might actually be a very good trade.

    The Dickey trade was bad and the Marlins trade was so-so. I think this was primarily a failure of process. He made three mistakes: (1) he went all in with a 75 win team; (2) he didn’t target the very best; and (3) he treated the Dickey trade like it was for four years of Dickey, not one year. You don’t pay for the right to ink an extension.

    But to AA’s credit he learned his lesson. The next time was very different. He bet on a high true talent team, target the very best. Donaldson, Price, and Tulo > > > Reyes, Dickey and Buehrle.

    You also ignored the Wells trade, one of the greatest salary dumps of all time.

    Now to AA’s draft record. You say he’s “one of the best executives in the league when it comes to drafting and developing.” What’s your evidence for this?

    True, he nabbed some nice arms in his early drafts. From 2010 to 2012, he picked Syndergaard, Stroman, Musgrove, Sanchez, Borucki, DeSclafani, Norris and Dyson. But to properly evaluate that, you should remember that he had 21 (!!!) 1st, 2nd and comp round picks in those three years. Twenty-one! Plus the bonus room that goes with them. Also, a team really should be getting 2 or 3 legit major leaguers in every draft just to keep pace, so I’m not sure how impressive that haul really is. I think as Blue Jay fans we were groomed for low expectations after the truly lousy Ricciardi drafts.

    In his later drafts (2013-2015), his best pick so far is probably Matthew Boyd. Danny Jansen also looks like a major leaguer. After that, the best hopes for extracting some major league value are probably SRF, Romano, Murphy and Bergen.

    AA was great at acquiring draft PICKS, but not so great at using them.

    Liked by 1 person

  4. I don’t think you go far enough or mention the biggest issue with AA and that’s contracts and salary management. The Marlins trade sent tons of potential away, but the worst part were the contracts we got back. We bailed out Miami of all its terrible deals. In an attempt to maneuver, AA then trades Reyes for an even worse salary/contract in Tulowitzki. The Russell Martin contract was atrocious. Rogers was never going to spend more than what he took on from the Florida deal. At that point he was screwed. From then on he was doing patchwork at the detriment to the long term future of the team. Everyone forgets that when AA took over, he stated he was committed to building a team that could compete every year, and then he abandoned his rebuild with the surprise of Bautista and Encarnacion emerged (both JP guys).

    *A reminder, Shapiro traded Cliff Lee to Phili the same year as AA traded Halladay to them, yet he got Carlos Carrasco and we got shit.

    Also, AA was actually good at acquiring extra draft picks, however, his record at drafting was mediocre at best.

    If it wasn’t for the Josh Donaldson trade, AA would be looked at as a terrible GM by the morons who think he was a great one.

    That’s all I have to say.


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