The 5 Worst Trades Made By Toronto Blue Jays GM Alex Anthopoulos

by Clayton Richer | Posted on Saturday, December 21st, 2013
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Alex Anthopoulos

As I peer out my window fixated on the ever growing pile of snow that I will soon be forced to shovel,  I find myself pondering the potential acquisitions the Toronto Blue Jays could make to solidify their roster for the upcoming baseball campaign. My thoughts carry me to my third base line seat at the Rogers Centre and, while reminiscing about fresh peanuts and $10 adult beverages, I soon reflect on the trigger pulling, team-friendly moves Blue Jays General Manager Alex Anthopoulos has made to acquire the likes of Colby Rasmus and Brett LawrieThe man known to the Blue Jays faithful as the “Silent Assassin” has been known to fleece the odd GM. He has traded for players who have not lived up to their lofty expectations and grown out of favor with their respective Managers. However, have you ever thought about the worst deals that Anthopoulos has made since taking over the helm of Blue General Manager on October 3rd, 2009 from the incumbent J.P. Ricciardi? Here is my list of five transactions that one could agree Anthopoulos would like a mulligan on.

1. Mike Napoli for Frank Francisco: On January 11th, 2011 Alex Anthopoulos made the trade that defines him as a General Manager by sending Vernon Wells and his monstrous, financially strapping contract to the Los Angeles Angels in return for Mike Napoli and Juan Rivera. However, Just 2 weeks later Anthopoulos reciprocated the favor making his worst lopsided trade to date exchanging the newly acquired Napoli for veteran reliever Frank Francisco of the Texas Rangers. Napoli would go onto bat .320 and crush 30 home runs in 113 games that season for the Rangers while Francisco only lasted one season with the Jays.

2. Aaron Hill and John McDonald for Kelly Johnson: I will agree that at the time of the deal it seemed like a wash. Both Hill and Johnson were set to become free agents and both had grew stagnant in their current environment leading up to the trade. Hill rejuvenated his career in the desert hitting .315 in the last 33 games of the 2011 season with Diamondbacks and continued that trend into 2012 batting .302 with 26 bombs while winning a Silver Slugger award. As for Kelly Johnson, he whiffed his way out of Canada posting a pathetic .225 average and fanned 159 times in 2012. Oh, did I mention the Jays also sent fan favorite and web gem master John McDonald to Arizona in the deal as well?

3. Mike Aviles and Yan Gomes for Esmil Rogers: On it’s face this deal is not mind blowing. However, the current catching epidemic and the eventual demise and departure of J.P. Arencibia obviously plays into my rationale. Gomes blossomed into an everyday player last season for the Indians batting .294 with an .826 OPS and 11 home runs proving he is a major league talent. Aviles was his steady self and a valuable asset off the bench and the veteran presence you would expect. In a time when the Blue Jays value catchers at a premium they dealt Gomes as an after-thought, a move that paid dividends immediately for the Tribe. Don’t get me wrong, Esmil Rogers has major league stuff but he also has an earned run average just under 5.00.

4.  Francisco CorderoBen Francisco ,Asher WojciechowskiCarlos PerezDavid Rollins , Joseph Musgrove and Kevin Comer for J.A. Happ, David Carpenter and Brandon Lyon: The Jays shipped a couple of veterans and a plethora of pitching prospects, three of which were 1st round selections, for a bottom of the rotation starter in Happ. Who knows in 5 years how this deal will shape out? It now seems like an awful steep ransom to pay for a starter with a career earned run average over 4.00.

5. Roy Halladay for Kyle Drabek, Travis d’Arnaud and Michael Taylor: I realize Anthopoulos’s hands were tied on this deal, but 4 seasons have past and not one single player has matriculated into an everyday major leaguer. The acquisition of Taylor turned into Brett Wallace, who was eventually flipped for Anthony Gose. The speedy Gose has all the tools but had a disappointing 2013 season. Currently the jury is out on whether he will ever be more than a fourth outfielder at the major league level. Drabek struggled at the major league level with his control and composure before suffering yet another season ending injury and d’Arnaud was used as trade bait to acquire R.A. Dickey. We all know what the “Doc” has done since returning south of the border. Now it’s time to see what Drabek and Gose can do in 2014.

More often than not Anthopoulos walks away the winner in his savvy but silent deals, but these are 5 questionable transactions that came to mind during my winter doldrums that may not go in the favor of the crafty canuck. Until the next deal, stay warm and remind yourself spring training is only 55 days away.

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Clayton Richer
About the Author

Clayton Richer is the Owner of Baseball Hot Corner and a Toronto Blue Jays enthusiast. Follow and interact with Clayton on Twitter @MLBHotCorner or @ClaytonRicher

  • bob l

    i think his worst trade did not even make your list. last year’s trade for dickey has to be number one. gave up a catcher that could be desperately used now and a pitcher who has the potential to be lights out for an aging knuckballer. give me a break! as far as your list goes,i think number four should be higher. too many prospects for happ.

    • Clayton Richer


      I mulled over adding the Dickey deal but was hoping to give it another season before I ruled the deal a bust.

      • PL78

        Gotta agree, d’Arnaud was far too steep a price to pay for Dickey, but then throw in Syndergaard and this one is going to be brutal. Both d’Arnaud+Syndergaard are far better fits on the Jays than Dickey.

        The Napoli one was probably the dumbest trade of the 2000s though. Just totally ridiculous. He so won everything by getting ANYTHING for Wells, as well as eating the entire contract, then gives away Napoli for a middle reliever before he even suited up for the Jays. You don’t do that. Napoli would have out-hit JP and/or Lind, and was just a heckuva lot more valuable than Francisco.

        I wonder if Beane ever calls him and says “Hey, remember when I grabbed E5 just to let you know you were effin up, but then let you have him back when you realized your mistake?” Because that is definitely what happened. Luckily Moss decided to mash, but that A’s team with a guy like Edwin at DH/1B? Wow.

        • Gannicus

          One of the dumbest trades in the 2000s? At the time, our system was stocked with young promising catching prospects D’Arnaud, Jimenez, Perez, Gomes, Nessy (Some obviously more promising than others) with a young JPA ready for a crack at full time MLB duty. In hindsight, sure it didn’t work out but calling it one of the dumbest trades of the 2000s is quite laughable. After he got over his injury Franky was a solid closer for the Jays and we had bullpen problems the year before. It’s like blaming every single team for not drafting Mike Trout before the Angels (late first round). Sure in hindsight it looks bad but the context of each situation needs to be considered. As for your Beane/AA thing it seems you base a lot of what you say off narratives you write. They’re interesting and all but write a book, don’t try and pass these things off as facts.

          For me? I think the worst trade has got to be TDA/Synder for Dickey because he believed this would push us over and we would win in 2013. Those guys were close enough to contribute in a years time (or less in TDA’s case).

        • RR427

          I hope you only mean just the Jays when you say that it’s the dumbest deal of the 2000s. If not then I’m pretty sure that that dubious honor goes to the Marlins for giving up Miguel Cabrera and Dontrelle Willis for Burke Badenhop, Cameron Maybin, Mike Rabelo, Andrew Miller, Eulogio De La Cruz and Dallas Trayhern.

    • http://BellMobility Bobby

      Lots of Catchers have been let go.D’Arnault,Gomes,Arencebia,Napoli,also,young Perez.Now,we got Navvaro,who isn’t great defensively either.Gomes is the one that hurts.Syndergaard is one that could blossom into an Ace,his stuff is great.

  • C Cheng

    Eventually the Florida and Mets deal will be 1, 2 on this list so there’s no harm putting them up now.

    • PL78

      AA isnt the GM of those teams, you misreader.

      • Marc

        Um, You’re the one who is misreading. He is referring to the deals for Johnson/Reyes & the deal for Dickey.

        Reading comprehension isn’t that hard bud.

  • John

    You failed to mention that Francisco ended up netting us a sandwich pick, which turned out to be Matt Smoral. That was a reason why AA targeted Francisco, knowing he was going to be a Type B. Also, none of the players we gave up to the Astros project to be much. Asher Woj may turn into a high-leverage reliever, but the rest are all pretty meh.

    • back seat driver

      People will *always* conveniently ignore information that does not fit their narrative. For example, within the Francisco / Napoli deal, there’s more than just draft pick compensation.

      What fans don’t realize is that had we kept Napoli, then we would likely have lost EE.

      By 2011, EE had already been relieved of his 3B duties. Arencibia was a rookie so he would very likely have taken full-time catching duties. Lind was transitioned to full time 1B. That leaves Napoli as the backup C, backup 1B, primary DH.

      Considering that EE did nothing spectacular in 2010, he was very expendable. In fact, EE was actually claimed on waivers (by Oakland), was subsequently released, and then re-signed with the Blue Jays. That’s how expendable he was.

      Adding Napoli would have likely meant goodbye EE.

      Again, this is information that should be presented when considering WHY the Blue Jays flipped Napoli in the first place.

  • MTGJays

    No one knew Napoli was going to hit like that – he never had before. At the time it also seemed like JP was gonna be the next big guy behind the plate. I would do the Marlins trade over again in a heart beat. HIndsight is always 20/20. You can look back and criticize all of these deals, but they were definitely not criticized at the time. Stupid. I do agree that AA gave up too much for Happ and way too much for Dickey. With Dickey, I see where he was going. Dickey just won the CY Young, and AA felt he needed an ace to really put the Jays over the top. The knuckleball is not hard on the arm, so I don’t care that Dickey is pushing 40. Many knuckleballers pitched very well into their 40s and are in the HOF. See Charlie Hough.

  • mC

    Thanks to AA for trading Syndergaard and Darnaud and Buck to the Mets for Dickey and a couple of magic beans.

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