Justin Upton: Yay Or Nay?

(Courtesy of The AP)

The Yankees have been and continue to be without one of their starting outfielders.  The Diamondbacks are rumored to be interested in trading a young, talented outfielder.  The trade deadline is less than 2 weeks away.  It doesn't take a Mensa International-qualifying IQ score to connect these dots.  When somebody like Justin Upton is supposedly on the trade block, of course the Yankees are going to be involved in the rumors.  There hasn't been a ton of discussion about just how heavily involved the Yankees are in the Upton market right now, but my expectation is that the discussion will only intensify once the latest diagnosis on Brett Gardner is revealed and the deadline draws closer.

Regardless of what happens with Gardner, I don't think the Yankees are in a situation where they NEED to make a move, especially one that will incur as much lost-prospect cost as Upton.  But it's not every day that a player of Upton's caliber ends up being available, so what I'm struggling to answer for myself is whether or not the Yankees SHOULD go after Upton if Arizona is serious about moving him and he's serious about being willing to accept a trade to New York (one of his no-trade clause teams).  There's a lot of factors in play here, so allow me to work them all for myself to see if I can come to a conclusion.


Case For-

On paper, this is almost a no-brainer for the Yankees.  They've already lost their left fielder this year, they're looking at losing their right fielder after this year, and Upton is a right fielder who could bring some much needed right-handed power to the lineup.  He's also a true 5-tool talent.  The Yankees have a couple of 3.5-4-tool guys (Granderson, Cano, Teix), but nobody with a skill makeup that rivals that of Upton.  He can hit for average, hit for power, field his position, run the bases, and he's got a plus outfield arm.  He's also only 24 years old, over a month away from his 25th birthday, and working on his 5th full Major League season.  Upton hasn't even reached his physical prime yet and he's already racked up 2 20 HR/20 SB seasons, 2 ASG selections, 1 Silver Slugger Award, and 1 top-5 MVP finish.  That's elite-level talent and production no matter how you look at it.

Upton also represents more than just a rental fill-in for the 2012 outfield.  He's currently under contract through the 2015 season at a rate ($12.833 million AAV) that is at least fair and at most a potential steal for a player of his caliber.  In a sense, Upton represents a "Version 2.0" trade of the past Swisher/Granderson trades.  He's even younger than they were when the Yankees traded for them, talent-wise he's a better player than either of them, and he's under team control for the foreseeable future.  Adding Upton would allow the Yankees to stay at the top of the food chain in the present and allow them to get younger and better for the future.

If there's a type of player to break the prospect bank for, it's Upton.  And if the D-backs are serious about moving him, it would be a classic buy-low scenario that would give the Yankees the best chance to land him without having to completely gut their farm system.  He would still come at considerable cost, but in theory the Yankees gain a bit of negotiating leverage with the D-backs being the proactive ones in getting the trade ball rolling.

Case Against-

As much as there is to like about Upton, both as an individual baseball player and a potential piece of the Yankee puzzle, there are some serious red flags with him.  For one, the fact that he's having such a down year is a little disconcerting.  Upton is following up a career year in 2011 with his worst season to date.  He currently sports a .325 wOBA, 97 wRC+, and his power is way down (.394 SLG, .121 ISO).  What makes these downward trends even more concerning is the fact that it's not the first time this has happened.  After a big 2009 season, Upton's follow-up 2010 campaign was nothing special, even factoring in his injury problems.  Being as young as he is, it's easy to say that he's still learning how to put everything together, but for a player with as much natural talent as Upton has, you hate to not see yearly progression.

The timing of this whole situation is also something that raises my eyebrows.  You don't sign a franchise player like Upton to a 6-year contract and then 2 years later put him on the trade block after a career year, especially when your team is coming off a postseason appearance the year before and still not out of the Wild Card race this year.  To me, that screams "Arizona's front office knows something that we don't" about Upton.  Be it concerns over injuries (legitimate considering Upton has only played more than 138 games in a season once) or attitude (also legitimate given some past incidents), there just seems like there has to be something else going on behind the scenes that's influencing this decision by Arizona.

And even with this being a buy-low trade scenario for the Yankees, any bit of potential trade leverage they could gain would be easily negated by Kevin Towers' familiarity with the Yankees' MiL system.  He's less than 2 years removed from his scouting job in the Yankee organization, and he won't allow Upton to go for prospects he isn't keen on.  The Yankees' chances of adding Upton for anything less than a big package of their top prospects is very low with Towers as a trade partner, and since the Yankees don't have a lot of Major League-ready players at positions the D-backs would be interested in, they would really have to sweeten the pot with multiple blue-chip low-level guys.  Is Upton worth giving up ManBan, Phelps/Nova, Sanchez, Austin, a/o Williams, if that's what it came to?

I'm still not sure what I'd do if I were in Cash's shoes.  The AAV of Upton's contract looks good, but he's looking at over $14 million coming his way in 2014, a number that the Yankees likely wouldn't want to pay if they are dead set on getting to the $189 million threshold.  That's one more factor to consider and one more thing that makes this situation so interesting.  If I had to guess right now, I would say the Yankees won't end up getting Upton, but I do think they at least owe it to themselves to make an offer and have the discussion.