If Justin Upton Becomes Available, Should the Blue Jays Target Him?

Alex Anthopoulos (AA) has a thing for players who have a fallen out of favor on their respectful teams. First it was Jose Bautista (When he was the Assistant GM in 2008), then it was Yunel Escobar (From the Braves in 2010), then it was Brett Lawrie (off-Season 2011), and then, his last work of art was Colby Rasmus (July 2011). So, when D-backs owner Ken Kendrick bashed Upton last month, suddenly he became a realistic option for the Blue J ays. And as Arizona falls further and further out of contention, it is becoming more and more probable that Upton, 24, hits the market.  Nick Piecoro from the Arizona Republic wrote yesterday that Arizona does covet Blue Jays shortstop prospect Adeiny Hechavarria, but it would require more than that (obviously) to get him.  He also points out a few reasons why it would make sense for the D-Backs to trade Upton. His first one is that they have a few outfield prospects in AAA that moving Upton would create jobs for, and his second is that they need a third baseman, shortstop and a top of the rotation starter. So, do the Blue Jays have these pieces, and should they push for Upton?

Third Baseman

Obviously the Blue Jays are not trading Brett Lawrie, as he has been their most consistent player this year, he is the reason for a whole lot of merchandise sales, and he is controllable for a long time! But what the Blue Jays do have is Yunel Escobar. Escobar, who is a SS right now, has the throwing arm to play third, and he definitely has the range for it. The only question mark would be his hands, which are pretty good as well, so he would likely be able to play third if asked to.


If Yunel Escobar was included in a trade, obviously the only SS left in Toronto would be Hech (or Omar Vizquel…). So, if Arizona would throw in Stephen Drew, who was also blasted by Ken Kendrick last month, Hech would become available for Arizona. This scenario is unlikely though because it is hard to imagine the Jays trading away both of their shortstops, although I guess it could happen.

Front Line Starter

The Blue Jays don’t have any MLB ready top of the rotation starters, or even back of the rotation starters, so this piece is NOT coming from the Jays by themselves. This situation would likely require a third team, similar to last season when the Jays traded for Edwin Jackson to get Colby Rasmus.

Here is a possible trade scenario…

To Blue Jays

Justin Upton (From Arizona)

Stephen Drew (From Arizona)

Carl Pavano (From Minnesota)

To Arizona

Yunel Escobar (from Toronto)

Adeiny Hechavarria (from Toronto)

Francisco Liriano (From Minnesota)

David Cooper (From Toronto)

To Minnesota

Travis Snider (From Toronto)

Chad Jenkins (From Toronto)

Carlos Perez (From Toronto)

Bobby Borchering (From Arizona)

Cash Considerations (From Toronto)

Just seems like something that could happen. Gives Minnesota some prospects, and some major league ready talent (Snider, Jenkins), fills Arizona’s needs of the three positions discussed earlier, and gives the Jays a veteran pitcher that they are lacking right now, plus gives them one of the most, if not the most feared outfields in the game with Bautista, Upton and Rasmus. I’m really bad at trade scenarios, so it is probably unfair for one of the teams, but I think if a trade for Upton would occur involving Toronto, Minnesota can be a suitable partner.

So to answer the original question of “Should Toronto Make a Push for Upton?”, I think the answer is yes. The price isn’t too high for what AA would be getting in return, and he could fill his pitching needs at the same time. Perez has no future in Toronto with d’Arnaud and A.J Jiminez in front of him, and Jenkins is expendable. David Cooper might play nicely in Arizona, a hitter friendly park, and Travis Snider becomes useless with the acquisition of Upton.

Obviously this is all hypothetical, but as a die-hard Jays fan, I would love to see AA do something like this.

Feel free to leave your comments below and we will discuss more about this topic, or anything else about the Blue Jays.

For more content written by me, check out bluejaysplus.com!

  • The5_5Hole

    It’s not often that you see these multi-team deals in baseball, but you make a feasible suggestion. I think the Dbacks are being hasty in their consideration of a possible trade for Upton. The guy is struggling, but let him work through it.

  • Mentoch

    @gideonturk Gotta say, I like most stuff you do via Twitter, but that’s a really awful fake trade. Will elaborate in your comments section.

  • gideonturk

    @Mentoch I said I suck at making trades…

  • Mentoch

    @gideonturk I’ll go into greater depth when I’m not restricted by 140 characters, but its got huge flaws. #NotTryingToBeMean

  • gideonturk

    @Mentoch not being mean. I take it as constructive criticism

  • Mentoch

    This is a really poor fake trade, for a whole bunch of reasons.
    The Diamondbacks arent receiving nearly enough in exchange for one of the best young players in baseball today.  I think that the only reason that Towers is dangling Upton out onto the market is to see if he can get a kings ransom in exchange for him.  This package isnt even close to that.  Lets look closely at what they are getting.
    1 – Adeiny Hechavarria is rated by Kevin Goldstein as the #20 prospect in the Jays system, and even though the Jays system is utterly stacked he’s still just a 3 star prospect who despite his inflated Vegas numbers is seen as a guy who is never going to hit at the major league level.  The closest comp for Hechavarria that I see is that he’s going to be like Rey Ordonez.  Someone who is a wizard with the glove, but who’s bat is just never going to play.  He’s probably the centerpiece of this deal, and he’s not even close to good enough to be that type of player.
    2 – Yunel Escobar is a player that I like quite a bit, and is clearly an above average major league shortstop.  He’s signed to a very team friendly contract, and would be an attractive asset in a deal, but he has significant warts.  In this deal you’re proposing that the Diamondbacks get him in order to shift him to plug their hole at third base, and even if he was having a typical Escobar season at the plate, his bat just isnt good enough to carry him at third.  Maybe at 2nd, but he just doesnt provide enough power to be a typical third baseman in the majors.  
    Aside from that, one of the D-Backs major prospects in their system is shortstop Chris Owings, I dont see shortstop as being one of their major weaknesses, though there is some buzz that he might be better off shifting off shortstop.  Getting two guys to block him doesnt make alot of sense.
    3 – The last piece they are getting from the Jays is first baseman David Cooper, and honestly, he’s nothing more than a throw in.  For his entire minor league career, he’s been seen as a player who will never hit enough to carry first base at the major league level, and his limited major league experience has done nothing to dissuade me (or anyone else for that matter) of that opinion.  Basically he profiles as a poor man’s Lyle Overbay, without the plus glove.  That’s not a player who’s even worthy of a roster spot.  Aside from that the Diamondbacks already have a player in Paul Goldschmidt who looks to be their first baseman of the future, and who’s really come into his own this year (and should be on the all-star team instead of Bryan LaHair).  
    Now, this brings me to the biggest flaw in the trade, and that’s Francisco Liriano, and there are many reasons why he’s a bad fit.
    A) He’s in no way a frontline starter.  
    In the past two years (217 innings), he’s put up a 5.09 ERA, while pitching in one of the most pitcher friendly ball-parks in the majors, in Target Field, good for a 80 ERA+.
    B) He’s an impending free agent.  
    If the Diamondbacks trade Justin Upton they are basically raising the white flag on competing this season, and so getting Liriano is worse than useless for them.
    In addition the D-Backs are also giving up a shortstop (though one who’s also a free agent, and has been horrendous this season), and also one of their top 10 prospects in outfielder Bobby Borchering.
    Another flaw here is that the Twins also are likely getting way more in return for what they are giving up, but that’s kind of besides the point, because including them in the first place was probably a mistake.  The more complex that you make a trade proposal the more ridiculous it frequently becomes. 
    Now, despite me tearing this idea to shreds, the actual idea of the Jays making a run at Upton makes tonne of sense.  Anthopolous has a history of going after distressed assets, and they also have a system that’s so stacked they can afford to give up the prospects required to put a package together.
    Here’s more what I’d be thinking…
    1 – AAA – CF – Anthony Gose
    Yes the D-Backs do have a few outfielders on their way up, and also an major league calibre outfielder they cant even find playing time for in Gerardo Parra.  However centerfielder Chris Young is a free agent after next season so a stud like Gose (even though his bat does have some warts), would be the perfect replacement for him.  He’s the type of stud prospect you’d need to include if you wanted to get this type of deal done.  (If not him AA right fielder Jake Marisnick might be a suitable replacement).
    2 – A – LHP – Justin Nicolino
    The Jays have 3 pitchers in their Lansing Lugnuts rotation who you could plug in here (Noah Syndergaard & Aaron Sanchez being the other two).  This is another STAR prospect that would need to be included in any deal for an asset as valuable as Upton.  You could sell the D-Backs on having a rotation built around Trevor Bauer, Tyler Skaggs, Justin Nicolino & Archie Bradley for years to come.  Yes this is a guy the Jays might be leery to give up, but when you have as many arms as the Jays do, its something they could certainly live without.
    3 – AAA – SS – Adeiny Hechavarria. 
    The buzz around the D-backs liking him is certainly there, and so he’s a perfectly acceptable piece to be put in, just not as the centerpiece.
    4 – AA – C – Carlos Perez
    This could practically be any other prospect in the Jays system.  Just another body to flush out the deal.
    This is a deal of a 4 star prospect (Gose or Marisnick), a 3.5 star prospect (Nicolino, or one of his rotation mates), and two 3 star prospect (Hechavarria & Perez).  That’s what its going to take to get Upton, and even that might not get it done.  

  • StatMojo

    @xbaggypants @fansided @CalltothePen while the Blue Jays rank 17th overall in OPS, they are 26th in ERA, maybe a bigger need there.

  • xbaggypants

    @StatMojo I’d have to agree, though the asking price might be steep for Garza, Hamels etc. Are the Jays a playoff team? I’d like to hope so.

  • bballbigbrother

    I have to agree with a lot of the sentiment below. I could see the Jays liking Upton alot, but I have to assume that Anthopoulos would want to spend his incredible wealth of prospects elsewhere.
    Should they choose to make a run at someone, their needs on the mound far outweigh their needs in the outfield. Waiting for free agency would be a smarter move on Hamels, but the Jays could make some decent noise by making a run at Garza. Or if they really want to push a blockbuster package out there, they have the pieces to float toward Seattle and see if they are willing to part with King Felix.